We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation Rentals in Chestertown, MD and nearby

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
mm/dd/yyyy mm/dd/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Payment Protection
    Use a credit card to book with our Peace of Mind Protection.Learn more
    Find a rental
    Price per night
    Min
    to
    Max
    Bedrooms
    Any
    Amenities
    Select
    Payment
    Select
    Go to map view
    More filters
    All 65 Rentals in the Chestertown Area
    loading...
    From
    $99
    / Night
    Payment Protection
    View Details
    1 / 10
    5 of 5 stars (5) Excellent
    Chestertown
    1 Bedroom / 1 Bathroom / Sleeps 4
    travelers have booked this property
    Overview Reviews (5) Make Inquiry
    From
    $145
    / Night
    Payment Protection
    View Details
    1 / 11
    5 of 5 stars (1) Excellent
    Chestertown
    3 Bedrooms / 1 Bathroom / Sleeps 7
    travelers have booked this property
    Overview Reviews (1) Make Inquiry
    From
    $120
    / Night
    Payment Protection
    View Details
    1 / 28
    5 of 5 stars (2) Excellent
    Chestertown
    1 Bedroom / 1 Bathroom / Sleeps 4
    travelers have booked this property
    Overview Reviews (2) Make Inquiry
    From
    $295
    / Night
    Payment Protection
    View Details
    1 / 12
    4.5 of 5 stars (3) Very good
    Chestertown
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    travelers have booked this property
    Overview Reviews (3) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Internet Access
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Located close to both Chestertown (15 minutes) and Rock Hall (30 minutes), MD this quiet, simple but energetic space is an ideal gathering place for families and friends. Stay here and relax the entire visit or explore the many activities, restaurants and cultural venues available in the Kent... View all property information
    Make Inquiry
    Location Information
    Chestertown, Maryland 21620
    3 of 5 stars Reviewed October 18, 2014
    If the unit is under construction, do not rent it. We should have been notified of the construction and given the opportunity to cancel.
    See all reviews

    The following rentals are within 25 miles of Chestertown, Maryland.

    From
    $350
    / Night
    Payment Protection
    View Details
    1 / 25
    5 of 5 stars (3) Excellent
    Annapolis
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (3) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Fireplace
    • Grill
    • Housekeeping...
    • Internet Access
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Half a block to walk to the Naval Academy Stadium and minutes away from stunning Annapolis town center. This adorable little cottage has lots of sleeping and great outdoor space. Sun Porch & Plenty of parking. A perfect place to relax and enjoy Annapolis, the property is available all year around... View all property information
    Make Inquiry
    Location Information
    Annapolis, Maryland 21401
    5 of 5 stars Reviewed April 23, 2015
    beautiful cottage in a perfect location. 5 min walk to the Navy Stadium. 10 min walk to the historic downtown area where there are many specialty shops, restaurants, taverns and...
    5 of 5 stars Reviewed April 15, 2015
    I've used the "cottage" a few times on recommendation of a friend as I do business often in Annapolis and have found it to be convenient, comfortable and well cared for. With its...
    See all reviews
    From
    $209
    / Night
    Payment Protection
    View Details
    1 / 11
    Stevensville
    2 Bedrooms / 1 Bathroom / Sleeps 6
    travelers have booked this property
    Overview Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Come to our beautiful vacation home and enjoy the scenic view while having fun on the water. Love Point Bay Vacation Home is at the mouth of the Chester River, where it connects to the Chesapeake Bay on Maryland's Eastern Shore. You will feel right at home, yet free of your everyday stress. Leave... View all property information
    Make Inquiry
    Location Information
    Stevensville, Kent Island 21666
    From
    $800
    / Night
    Payment Protection
    View Details
    1 / 31
    5 of 5 stars (1) Excellent
    Annapolis
    3 Bedrooms / 2 Bathrooms / Sleeps 10
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Safe
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Bright, open, waterfront contemporary located on a landscaped property with magnificent views of Lake Ogleton! Pier (4'MLW) for your boat, crabbing, fishing and swimming. Bay Ridge Subdivison has great views, sandy beaches, streets for jogging, nature walks, and just great places to chill.... View all property information
    Make Inquiry
    Location Information
    Annapolis, Maryland 21036
    From
    $350
    / Night
    Payment Protection
    View Details
    1 / 25
    5 of 5 stars (1) Excellent
    Annapolis
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    traveler have booked this property
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Housekeeping...
    • Internet Access
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Half a block to walk to the Naval Academy Stadium and minutes away from stunning Annapolis town center. This adorable little cottage has lots of sleeping and great outdoor space. Sun Porch & Plenty of parking. A perfect place to relax and enjoy Annapolis, the property is available all year around... View all property information
    Make Inquiry
    Location Information
    Annapolis, Maryland 21401
    5 of 5 stars Reviewed April 13, 2015
    I had the pleasure of staying at this beautiful cottage for one night. It was very clean, comfortable, and had a really cozy ambiance. The neighborhood was quiet and peaceful and...
    See all reviews
    From
    $325
    / Night
    Payment Protection
    View Details
    1 / 6
    Annapolis
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Our home is located in the Eastport section of Annapolis and just a short walk to Main street, the Historic District and the Naval Academy. We have a large back yard that's great for entertaining, plenty of off street parking and we're just across the street from the best view of the Chesapeake Bay... View all property information
    Make Inquiry
    Location Information
    Annapolis, Maryland 21403
    From
    $250
    / Night
    Payment Protection
    View Details
    1 / 26
    5 of 5 stars (1) Excellent
    Annapolis
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    traveler have booked this property
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dryer
    • Fireplace
    • Grill
    • Housekeeping...
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    History, waterfront, rooftop restaurants, wine bars, sailing, kayaking and more. We have everything here in Annapolis - USNA, sailing, culture, world-class restaurants & a vibrant, walkable capital city! Here in Upper Eastport, on a cul de sac, we are a short walk to the Historic Harbor & 3 blocks... View all property information
    Make Inquiry
    Location Information
    Annapolis, Maryland 21403
    5 of 5 stars Reviewed July 15, 2014
    If you want a cozy place to relax this is the place. Yard was perfect for my dog to run around and I did not have to worry it was all fenced in. Love to grill so I was able to...
    See all reviews
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    From
    $600
    / Night
    Payment Protection
    View Details
    1 / 14
    Annapolis
    1 Bedroom / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Hot Tub
    • Internet Access
    • Ocean Views
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    This beautiful and elegant 1 BR loft with 2.5 bath, that is nestled in a quiet but vibrant private residential community equipped with 2 swimming pools, 2 tennis courts and a restaurant, which sits on the water. This property is located in the Chesapeake Bay area. With access to the beach to the... View all property information
    Make Inquiry
    Location Information
    Annapolis, Maryland 21403
    From
    $85
    / Night
    Payment Protection
    View Details
    1 / 27
    Baltimore
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Internet Access
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Easygoing couple hosting this sunny bedroom, on a tree-lined street, two blocks from Johns Hopkins Homewood campus and Medstar's Union Memorial Hospital. This large bedroom has a private entrance and is well furnished, including an office area, storage space & access to a workout area. The... View all property information
    Make Inquiry
    Location Information
    Baltimore, Maryland 21218
    From
    $140
    / Night
    Payment Protection
    View Details
    1 / 6
    Baltimore
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    This 840 sq. ft. row home is located just off of I-95 and I-695, 9 miles from BWI airport, 3.5 miles from downtown Inner Harbor, 0.6 miles from St. Agnes Hospital, and a short driving distance from numerous other hospitals, including Johns Hopkins, Mercy Medical Center, and University of Maryland... View all property information
    Make Inquiry
    Location Information
    Baltimore, Maryland 21223
    From
    $235
    / Night
    Payment Protection
    View Details
    1 / 9
    Rock Hall
    3 Bedrooms / 1 Bathroom / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Grill
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Charming 3 bed / 1 bath single family home with screened in front porch. Relax on the rocking chairs as you take in the charm of this lovely town on one of the prettiest streets in Rock Hall. Ample parking, large back yard with BBQ, tables and chairs to relax with family and friends after spending... View all property information
    Make Inquiry
    Location Information
    Rock Hall, Maryland 21661
    From
    $200
    / Night
    Payment Protection
    View Details
    1 / 18
    5 of 5 stars (1) Excellent
    Baltimore
    3 Bedrooms / 1 Bathroom / Sleeps 8
    travelers have booked this property
    Overview Reviews (1) Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    In Baltimore on vacation? Going to Camden Yards or to see a Ravens game? Attending a conference at the Convention Center? Visiting the University of Maryland medical school or hospital?What if I told you you could walk to any of the above in less than 10 minutes?! You will not find a better... View all property information
    Make Inquiry
    Location Information
    Baltimore, Maryland 21230
    5 of 5 stars Reviewed January 13, 2014
    Our family group of eight (family of four with two young kids and two sets of grandparents) had a wonderful stay at this vacation rental between Christmas and New Year's. You...
    See all reviews
    From
    $203
    / Night
    Payment Protection
    View Details
    1 / 6
    Baltimore
    2 Bedrooms / 4 Bathrooms / Sleeps 4
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Internet Access
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Rent the entire House or Rent a Private Room. See my listings for individual private room. This listing for the entire house. If you stay for a 40 nights or more FREE WEEKLY MAID SERVICE. (2 Private Bedrooms have private Bathrooms). Both bedrooms have full/queen beds. If you are in Baltimore... View all property information
    Make Inquiry
    Location Information
    Baltimore, Maryland 21205
    From
    $150
    / Night
    Payment Protection
    View Details
    1 / 26
    4.5 of 5 stars (7) Very good
    Baltimore
    3 Bedrooms / 1 Bathroom / Sleeps 6
    travelers have booked this property
    Overview Reviews (7) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Built in the 1920s, this Tudor style house retains its original charm, it is spacious and creatively painted, with hardwood floors throughout. Fully furnished and decorated with artwork, rugs and antiques from our travels around the world. Two bedrooms with comfortable queen size beds, and one with... View all property information
    Make Inquiry
    Location Information
    Baltimore, Maryland 21218
    5 of 5 stars Reviewed August 31, 2014
    We came into town early for vacation. Friends joined use mid-week for a 4 day conferance down town. The home was the perfect location. Close to grocery store, dinning too. Robert...
    5 of 5 stars Reviewed July 13, 2014
    Stayed here for one week while we visited the capitol and surrounding areas. Townhouse is great and we had no problems. It was hot outside and all the AC units worked well. Very...
    See all reviews
    From
    $150
    / Night
    Payment Protection
    View Details
    1 / 18
    Baltimore
    3 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Internet Access
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Built in the 1920s, this Tudor style house retains its original charm, it is spacious and creatively painted, with hardwood floors throughout. Fully furnished and decorated with artwork, rugs and antiques from our travels around the world. Two bedrooms with comfortable queen size beds, and one with... View all property information
    Make Inquiry
    Location Information
    Baltimore, Maryland 21218
    From
    $750
    / Night
    Payment Protection
    View Details
    1 / 26
    5 of 5 stars (2) Excellent
    Annapolis
    6 Bedrooms / 4 Bathrooms / Sleeps 13
    travelers have booked this property
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Pool Table
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    The Perfect House for a Navy Football Game Weekend!! This is a beautiful historic property within walking distance of downtown Annapolis and the Navy-Marine Corps Stadium. With six bedrooms (two queen beds, three fulls and two twins) the house could comfortably sleep up to 12. Additional rooms... View all property information
    Make Inquiry
    Location Information
    Annapolis, Maryland 21405
    5 of 5 stars Reviewed September 27, 2014
    Our large group of women in their 30's had a great time and everyone had a comfortable bed and plenty of room. Caitlyn was very responsive, friendly and accommodating from the...
    5 of 5 stars Reviewed August 11, 2014
    We just returned from our sailing weekend in Annapolis and had an amazing time staying at this lovely house for the weekend. The house was perfect for a larger group. The large...
    See all reviews
    From
    $250
    / Night
    View Details
    1 / 23
    Annapolis
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Comfortable Timber Frame deep waterfront home in Annapolis close to USNA. Private wooded setting with wonderful water views. 3 miles to Annapolis Historic district. Easy commute to Washington, DC and Baltimore, MD. Tastefully furnished and equipped. View all property information
    Make Inquiry
    Location Information
    Annapolis, Maryland 21409
    Get the List
    From
    $120
    / Night
    Payment Protection
    View Details
    1 / 7
    5 of 5 stars (5) Excellent
    Baltimore
    1 Bedroom / 1 Bathroom / Sleeps 2
    travelers have booked this property
    Overview Reviews (5) Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Newly renovated, fully furnished, spacious one bedroom apartment in 19ty century rowhouse in Baltimore's historic Mt Vernon neighborhood. This second floor walkup apartment is located on a linden tree-lined street just steps from restaurants, cultural attractions, historic sites, and shopping.... View all property information
    Make Inquiry
    Location Information
    Baltimore, Maryland 21201
    5 of 5 stars Reviewed April 8, 2015
    The Mt Vernon area is so close to everything we wanted to visit. There is public transit readily available and the streets are pedestrian friendly. The Light Rail from the...
    5 of 5 stars Reviewed September 19, 2014
    We have stayed in Baltimore several times and this is by far the most comfortable stay we have experienced. We felt we left with new friends. The apartment is lovely and the...
    See all reviews
    From
    $120
    / Night
    Payment Protection
    View Details
    1 / 4
    Baltimore
    1 Bedroom / 1 Bathroom / Sleeps 2
    travelers have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    One bedroom, one full bathroom corporate apartment in owner occupied, elegant Victorian townhome in historic Mt Vernon neighborhood. Unit is fully furnished with a queen sized bed, full bathroom with tub/shower, and fully-equipped kitchen. Our Location: Nestled on a tree-lined side street, we're... View all property information
    Make Inquiry
    Location Information
    Baltimore, Maryland 21201
    From
    $425
    / Night
    Payment Protection
    View Details
    1 / 30
    4.5 of 5 stars (2) Very good
    Annapolis
    4 Bedrooms / 2 Bathrooms / Sleeps 9
    travelers have booked this property
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Our beautifully-appointed home pays homage to the Colonial Period. It comfortably sleeps eight guests with four bedrooms and 2.5 baths. It boasts elegant dining and living rooms. Enjoy the quiet street and an easy stroll to downtown Annapolis. We have taken great care and paid pain-staking... View all property information
    Make Inquiry
    Location Information
    Annapolis, Maryland 21401
    From
    $250
    / Night
    Payment Protection
    View Details
    1 / 17
    5 of 5 stars (3) Excellent
    Rock Hall
    3 Bedrooms / 2 Bathrooms / Sleeps 7
    Overview Reviews (3) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    This Spacious Home provides 3 Bedrooms and 2 bathrooms. Each room sleeps 2 people comfortably, and an old fashion cot is provided to sleep one more. This home is completely equipped with all the comforts of home. The Central location is in the heart of the Marina district, steps from Waterman’s... View all property information
    Make Inquiry
    Location Information
    Rock Hall, Maryland 21661
    From
    $299
    / Night
    View Details
    1 / 12
    5 of 5 stars (1) Excellent
    Perryville
    5 Bedrooms / 2 Bathrooms / Sleeps 13
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Feel yourself unwind as soon as you pull in the drive and take in the splendid water views from the decks of this private home on the North East River. Listen as the blue herons call while fishing in the shallows, and watch the bald eagles and ospreys circle in search of prey. The river's mood... View all property information
    Make Inquiry
    Location Information
    Perryville, Maryland 21903
    From
    $300
    / Night
    Payment Protection
    View Details
    1 / 9
    Annapolis
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • x
    • Wheelchair access
    • Elder access
    About this property
    This is the newly renovated 780 sf studio unit that is on the ground floor of a main house that is similarly titled and on the same property. Striking and dramatic 8700 - 9000 sf contemporary, new loft style renovation of the main house with exposed structure and mechanical systems that serves as... View all property information
    Make Inquiry
    Location Information
    Annapolis, Maryland 21401
    From
    $700
    / Night
    Payment Protection
    View Details
    1 / 6
    Annapolis
    5 Bedrooms / 6 Bathrooms / Sleeps 12
    traveler have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Our home is brand new & only one block from the Naval Academy Stadium on Gibson Rd (you can see the stadium from M. bedroom balcony). With, 4 bedrooms upstairs & 1 bedroom down, all the bedrooms have their own full bath. There is also a family room on the second floor with a mini bar, sink & pull... View all property information
    Make Inquiry
    Location Information
    Annapolis, Maryland 21401
    From
    $115
    / Night
    Payment Protection
    View Details
    1 / 5
    Galena
    2 Bedrooms / 1 Bathroom / Sleeps 5
    Overview Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    A very relaxed area to go swimming, tubing, fishing and boating. You have to get in a car to go to a store about 2 miles for food , etc. We have nice restaurants near by and also golf about 5 miles down the road. View all property information
    Make Inquiry
    Location Information
    Galena, Maryland 21625
    From
    $200
    / Night
    Payment Protection
    View Details
    1 / 7
    5 of 5 stars (4) Excellent
    Baltimore
    5 Bedrooms / 5 Bathrooms / Sleeps 6
    travelers have booked this property
    Overview Reviews (4) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Safe
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Large family home available from June 15-Aug 20, 2014. Negotiable start and end. In the University area of Baltimore-Hopkins, Loyola, Morgan State, Univ Maryland. Fenced in yard, private patio, finished basement with full bath and guest room as well as an in-laws attic room with private bath. Fully... View all property information
    Make Inquiry
    Location Information
    Baltimore, Maryland 21211
    4 of 5 stars Reviewed January 3, 2015
    It is the house that keeps going. Lots of rooms that do not always make sense (eg. one bathroom with sink and toilet only and another with toilet and tub only), but adds to the...
    5 of 5 stars Reviewed August 12, 2014
    Marta and Kelly's house was a godsend! It was PERFECT and may have been the single best planning decision we made for our wedding weekend. I rented it for my immediate family...
    See all reviews
    From
    $199
    / Night
    View Details
    1 / 14
    5 of 5 stars (4) Excellent
    Baltimore
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Reviews (4) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Internet Access
    • Satellite TV
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Come stay aboard our FABULOUS houseboat, berthed in one of the most convenient marinas for exploring all that Baltimore has to offer! Custom designed inside and out, this floating home features handcrafted wood trim and cabinetry, an open style main salon and dining area, a fully appointed galley... View all property information
    Make Inquiry
    Location Information
    Baltimore, Maryland 21231
    5 of 5 stars Reviewed September 17, 2014
    The only thing better than being in Baltimore for the Sailabration Blue Angels Show and massive fireworks display was being on the Scorpius for the wonderful weekend! We had...
    5 of 5 stars Reviewed October 23, 2013
    Loved being on the water!!! Walking distance to most of DC attractions and/or bus/Metro. Restaurant at end of pier sponsored a pet rescue night(Monday), which my 14 y.o...
    See all reviews
    From
    $325
    / Night
    Payment Protection
    View Details
    1 / 21
    Baltimore
    3 Bedrooms / 2 Bathrooms / Sleeps 9
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Welcome to Baltimore! If you are a sports fan than you have found your vacation home, step out our front door and walk through the turnstiles at Camden Yards, go another 500 yards and you will be at Ravens Stadium, The Baltimore Grand Prix runs right past the house! We are just 2 blocks away... View all property information
    Make Inquiry
    Location Information
    Baltimore, Maryland 21230
    From
    $400
    / Night
    Payment Protection
    View Details
    1 / 22
    5 of 5 stars (1) Excellent
    Annapolis
    3 Bedrooms / 6 Bathrooms / Sleeps 10
    traveler have booked this property
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Hot Tub
    • Internet Access
    • Ocean Views
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This spacious, airy and relaxing 3 bedroom Suisse Chalet sits on Mill Creek just off of the Chesapeake Bay and the Severn River. Located on Mulberry Hill Road, Annapolis, Maryland this beautiful and spacious Suisse Chalet is located 5 minutes from the United States Naval Academy, the community of... View all property information
    Make Inquiry
    Location Information
    Annapolis, Maryland 21409
    5 of 5 stars Reviewed April 9, 2015
    The home was located at a very continent location just 5-10mins drive to Naval academy and Annapolis downtown. The home was clean and have all the amenities. The water views from...
    See all reviews
    From
    $400
    / Night
    Payment Protection
    View Details
    1 / 23
    Annapolis
    2 Bedrooms / 2 Bathrooms / Sleeps 10
    traveler have booked this property
    Overview Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    ************* NEW LISTING - AVAILABLE NOW ************ SAILBOAT SHOW 2014 - $5000.00/wk POWER BOAT SHOW 2014 - $5000.00/wk CHRISTMAS 2014 - $5000.00/wk COMMISSIONING WEEK 2015 - $5000.00/wk Eastport cottage sleeps 10 - 2 bedrooms with sleeping loft - 1 full and 1 half bath - 2 premium queen... View all property information
    Make Inquiry
    Location Information
    Annapolis, Maryland 21403
    From
    $200
    / Night
    Payment Protection
    View Details
    1 / 18
    Annapolis
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    travelers have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    The perfect retreat for a family visiting Annapolis on vacation or for visiting your Johnny or Midshipman at the Naval Academy. This house is modestly priced yet has all the amenities and comfort of a home and the ability to eat in and cook your meals in our huge fully equipped kitchen or barbecue... View all property information
    Make Inquiry
    Location Information
    Annapolis, Maryland 21403
    From
    $575
    / Night
    View Details
    1 / 23
    Stevensville
    4 Bedrooms / 4 Bathrooms / Sleeps 14
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Beautiful 4 Bedroom, 4 Bath Quiet Waterfront Property, 3 queen bedrooms, 1 twin beds, 4 baths, two stories, fantastic master bedroom with mater bath complete with Roman soaking tub. Deck off of the master bedroom. Formal living room, Family room, Glass Sunroom, eat in kitchen, this spacious comes... View all property information
    Make Inquiry
    Location Information
    Stevensville, Kent Island 21666
    From
    $450
    / Night
    Payment Protection
    View Details
    1 / 7
    Annapolis
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    travelers have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Shellback house is a three bedroom, one and 1/2 bath historic townhouse in the heart of Downtown Annapolis with a private garden. The house has views of Ego Alley (Annapolis Waterfront) from the front stoop and the master bedroom. BOOK NOW FOR 2015 LEGISLATIVE SESSION AT STIPEND RATES! Please... View all property information
    Make Inquiry
    Location Information
    Annapolis, Maryland 21401
    From
    $350
    / Night
    Payment Protection
    View Details
    1 / 21
    Arnold
    4 Bedrooms / 2 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Clean, comfortable, family-friendly split-level home, fully furnished, washer and dryer, TV, cable, internet, wifi, quiet neighborhood with off-street parking, large shaded fenced back yard with deck for relaxing after a fun-filled day exploring Historic Annapolis, the Baltimore Harbor or our... View all property information
    Make Inquiry
    Location Information
    Arnold, Maryland 21012
    From
    $250
    / Night
    Payment Protection
    View Details
    1 / 15
    4 of 5 stars (2) Very good
    Rock Hall
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
    Overview Reviews (2) Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    The Cottage takes advantage of its unique environment with a large deck overlooking the extensive lawn and the tranquil waters of Spring Cove. The deck includes a dining set and barbeque grill.The first level includes a screened porch accessed through a first floor bedroom The Cottage is oriented... View all property information
    Make Inquiry
    Location Information
    Rock Hall, Maryland 21661
    4 of 5 stars Reviewed September 16, 2014
    My sisters and mother stayed three nights in this quaint house with great views of one of the marina's and cove area. The downstairs was perfect my mother, with a screened in...
    4 of 5 stars Reviewed August 19, 2014
    My family was looking for a relaxing getaway that would be an alternative to another week at the beach. We found the perfect spot at this cottage near Rock Hall. We rented with no...
    See all reviews
    From
    $200
    / Night
    Payment Protection
    View Details
    1 / 23
    5 of 5 stars (1) Excellent
    Baltimore
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    travelers have booked this property
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Gym
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    3 bedrooms in the heart of Hampden, the best neighborhood in Baltimore. Minutes walk to great restaurants & the many independent stores on The Avenue. Minutes drive to downtown (Camden Yards, M&T Stadium, the Baltimore Convention Center, the National Aquarium), as well as a quick drive to... View all property information
    Make Inquiry
    Location Information
    Baltimore, Maryland 21211
    5 of 5 stars Reviewed March 30, 2014
    We truly enjoyed our stay. What a perfect place. We loved the house, the neighborhood, and the books. Very comfortable, warm, and inviting. Oren took great care to make sure we...
    See all reviews
    From
    $160
    / Night
    View Details
    1 / 28
    5 of 5 stars (24) Excellent
    Baltimore
    1 Bedroom / 1 Bathroom / Sleeps 2
    travelers have booked this property
    Overview Reviews (24) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Internet Access
    • Satellite TV
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    This is a fully appointed in-laws corporate apartment on the third floor of an owner occupied guest house. If you need to accomodate more than 2 guests, there are also a two bedroom/one bath suite on the third floor and two bedrooms with private baths on the second floor that are available. Please... View all property information
    Make Inquiry
    Location Information
    Baltimore, Maryland 21202
    5 of 5 stars Reviewed August 24, 2014
    Our group of 8 converged on Baltimore for a wedding this past weekend, and the Empire House was absolutely perfect, in every way. You can park your car in the lot directly...
    5 of 5 stars Reviewed August 17, 2014
    We came from all the corners of the world for a wedding in Baltimore and wanted to be together. We found in the Mansion the ideal place: comfortable, elegantly appointed, and with...
    See all reviews
    From
    $180
    / Night
    Payment Protection
    View Details
    1 / 12
    Rock Hall
    1 Bedroom / 1 Bathroom / Sleeps 4
    travelers have booked this property
    Overview Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Enjoy the gentle tidal waters of the Chesapeake Bay and its tributaries from your private overlook. The Captain’s Quarters at Spring Cove is a crisp and contemporary second floor living space with great water views. An exterior stairway leads to an ample deck where you can enjoy breakfast and... View all property information
    Make Inquiry
    Location Information
    Rock Hall, Maryland 21661
    From
    $325
    / Night
    Payment Protection
    View Details
    1 / 11
    5 of 5 stars (1) Excellent
    Baltimore
    2 Bedrooms / 1 Bathroom / Sleeps 6
    travelers have booked this property
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Grill
    • Gym
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Pet Friendly, Super Convenient, Spacious Enough for the Whole Family The Aries is a new 2 bedroom houseboat between the trendy Fells Point and Canton neighborhoods at the Lighthouse Point Marina, with beautiful views of Fells Point and Canton from the top deck. Renters have use of the fitness... View all property information
    Make Inquiry
    Location Information
    Baltimore, Maryland 21224
    5 of 5 stars Reviewed May 29, 2014
    My husband and I stayed with our 17 year old son; plenty of space, lovely appointments, wonderful rooftop deck. Didn't need to bring a thing for the kitchen for cooking or...
    See all reviews
    From
    $225
    / Night
    Payment Protection
    View Details
    1 / 15
    5 of 5 stars (1) Excellent
    Baltimore
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (1) Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Joe's Boats is happy to welcome the Noble Pirate as the newest addition to our fleet. This eclectic 42' 1968 Chris Craft is a well appointed V hull boat that sleeps 3-4 comfortably. The boat is a tri-level with a master bedroom with a queen bed, twin fold out couch and a V birth. The Noble Pirate... View all property information
    Make Inquiry
    Location Information
    Baltimore, Maryland 21213
    5 of 5 stars Reviewed April 11, 2015
    The house boat Aries is spacious, clean, beautifully decorated, and centrally located in a beautiful area of the harbor. The boat is stocked with everything you need. Joe is very...
    See all reviews
    From
    $250
    / Night
    Payment Protection
    View Details
    1 / 15
    Baltimore
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Grill
    • Gym
    • Private Outdoor...
    • Safe
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    The Margaret Claire is a 50 ft houseboat located at Lighthouse Point Marina in Baltimore. The boat has one master suite along with a sleeper sofa and a full kitchen. The boat has amazing deck space with outdoor seating and a grill on the top deck. The boat has wifi and cable television and is well... View all property information
    Make Inquiry
    Location Information
    Baltimore, Maryland 21224
    From
    $250
    / Night
    Payment Protection
    View Details
    1 / 55
    4.5 of 5 stars (3) Very good
    Baltimore
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
    Overview Reviews (3) Make Inquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Ping Pong Table
    • Pool Table
    • Private Fishing...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    ************ RATE INCLUDES PLENTY OF ONSITE ACTIVITIES AND AMENITIES! ************** ****** THIS HOME IS A 2 BEDROOM TOWNHOUSE, PLUS A STUDIO APARTMENT UNIT IN LOWER LEVEL WITH 2 QUEEN BEDS, A FULL SIZE COMFORTABLE SLEEPER SOFA (No springs) + 2.5 BATHS ****** PLEASE NOTE THAT RATES FOR PERIODS... View all property information
    Make Inquiry
    Location Information
    Baltimore, Maryland 21221
    5 of 5 stars Reviewed July 1, 2014
    This townhouse is an end unit and private. Quiet, great location right on the water. 3 decks, had access to 2 kayaks and a paddle boat if we wanted. Plenty of room and it was...
    See all reviews
    From
    $595
    / Night
    Payment Protection
    View Details
    1 / 26
    Annapolis
    5 Bedrooms / 3 Bathrooms / Sleeps 20
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Internet Access
    • Ocean Views
    • Private Fishing...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Comfort & Style: Enjoy stunning Chesapeake Bay Views, Beach, Pier, Boat Slips, Park, Water Access, Fire Pit, Patio Heater and more! Charming cottage & detached studio/game room (both upgraded in 2013) offer gourmet kitchen with new stainless steel appliances, a second full kitchen in garden... View all property information
    Make Inquiry
    Location Information
    Annapolis, Maryland 21403
    From
    $480
    / Night
    Payment Protection
    View Details
    1 / 8
    Baltimore
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    A four flour condo on the water equipped with the latest amenities and modern furniture. It has an elevator and a sitting area and a BBQ on the roof. Ideal for couples or business travelers . View all property information
    Make Inquiry
    Location Information
    Baltimore, Maryland 21601
    From
    $299
    / Night
    Payment Protection
    View Details
    1 / 3
    Baltimore
    4 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    The apartments at 407 North Charles are located in the heart of downtown Baltimore close of a variety of dining and nightlife as well as easy access to major interstates for easy travel. Features of 407 North Charles Apartments include: Laundry in Apartment, Pets Allowed, Parking Garage Available... View all property information
    Make Inquiry
    Location Information
    Baltimore, Maryland 21201
    From
    $275
    / Night
    Payment Protection
    View Details
    1 / 11
    Baltimore
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Luxurious 3 bedroom 3 bathroom vacation apartment fully furnished. 5 min walk from the inner harbor, downtown area, and convention center. all new furniture recently furnished amenities include a gym and a Lounge area with a pool table 190/night View all property information
    Make Inquiry
    Location Information
    Baltimore, Maryland 21202
    From
    $500
    / Night
    View Details
    1 / 13
    Annapolis
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    NOTE: Please call me if you want to book my property. There have been security problems on all vacation rental sites. If anyone should ask you to wire funds please call me at the number listed on this site. Beautiful upgraded home in Eastport is perfectly located in small Cul De Sac... View all property information
    Make Inquiry
    Location Information
    Annapolis, Maryland 21403