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Vacation Rentals in Chestertown, MD and nearby

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All 57 Rentals in the Chestertown Area
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From
$295
Per Night
1 / 12
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Chestertown
3 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
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From
$140
Per Night
1 / 11
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Chestertown
3 Bedrooms, 1 Bathroom, Sleeps 7
Bookings
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From
$120
Per Night
1 / 28
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Chestertown
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
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From
$99
Per Night
1 / 10
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Chestertown
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (5) Make Inquiry Similar Properties
Amenities & Details
  • Microwave
  • Refrigerator
  • Internet Access
  • Stove
  • Parking
  • Safe
  • Outdoor Dining Area
  • Balcony
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
This artistic, light-filled one-bedroom apartment is located in historic Chestertown, MD. The space includes kitchen/living room combo, bedroom with queen size bed, bathroom with shower and tub. An air mattress can be set up in the living room for 2 additional guests. An outdoor deck with cafe... View all property information
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5 of 5 stars Reviewed November 12, 2014
Would definitely stay again or recommend to friends. Off the beaten path but a stone's throw from everything. Clean, nicely furnished with an eye for the aesthetic. Simple and...
5 of 5 stars Reviewed July 25, 2014
We enjoyed our stay in this very pleasant and bright apartment, walking distance to the visitor's center, the downtown with many shops and restaurants, and the Chester River. The...
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From
$259
Per Night
1 / 9
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Chestertown
1 Bedroom, 1 Bathroom, Sleeps 2
Details Make Inquiry Similar Properties
Amenities & Details
  • Stereo System
  • VCR
  • Internet Access
  • Stove
  • Microwave
  • Refrigerator
  • Central Heating
  • Linens Provided
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Camellia Cottage is a ca. 1950 ranch house apartment located on the property of the award-winning Brampton Bed & Breakfast Inn. The newest accommodation at our Chestertown Bed and Breakfast is a chic, Danish Modern furnished one bedroom flat. With it's own entrance, a fully equipped kitchen and a... View all property information
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From
$99
Per Night
1 / 10
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Chestertown
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (5) Make Inquiry Similar Properties
Amenities & Details
  • Microwave
  • Refrigerator
  • Internet Access
  • Stove
  • Parking
  • Safe
  • Outdoor Dining Area
  • Balcony
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
This artistic, light-filled one-bedroom apartment is located in historic Chestertown, MD. The space includes kitchen/living room combo, bedroom with queen size bed, bathroom with shower and tub. An air mattress can be set up in the living room for 2 additional guests. An outdoor deck with cafe... View all property information
Make Inquiry
5 of 5 stars Reviewed November 12, 2014
Would definitely stay again or recommend to friends. Off the beaten path but a stone's throw from everything. Clean, nicely furnished with an eye for the aesthetic. Simple and...
5 of 5 stars Reviewed July 25, 2014
We enjoyed our stay in this very pleasant and bright apartment, walking distance to the visitor's center, the downtown with many shops and restaurants, and the Chester River. The...
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The following rentals are within 25 miles of Chestertown, Maryland.

From
$800
Per Night
1 / 31
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Annapolis
3 Bedrooms, 3 Bathrooms, Sleeps 10
Details Reviews (1) Make Inquiry Similar Properties
Amenities & Details
  • Grill
  • Washer
  • Fireplace
  • Refrigerator
  • Garage
  • Parking
  • Microwave
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
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. Once... View all property information
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From
$250
Per Night
1 / 20
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Annapolis
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Reviews (1) Make Inquiry Similar Properties
Amenities & Details
  • DVD Player
  • Grill
  • Parking
  • Refrigerator
  • Fireplace
  • Microwave
  • Patio
  • Stove
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
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 & 3 blocks from Spa Creek, is this charming, cozy, easy-living place to relax, entertain & enjoy nature. Plenty of free parking- two... View all property information
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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...
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From
$250
Per Night
1 / 17
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Rock Hall
3 Bedrooms, 2 Bathrooms, Sleeps 7
Details Reviews (3) Make Inquiry Similar Properties
Amenities & Details
  • Dryer
  • Grill
  • Microwave
  • Pool
  • Refrigerator
  • VCR
  • DVD Player
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • 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
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From
$150
Per Night
1 / 17
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Baltimore
3 Bedrooms, 1 Bathroom, Sleeps 5
Bookings
Details Reviews (6) Make Inquiry Similar Properties
Amenities & Details
  • Microwave
  • DVD Player
  • Garage
  • Stove
  • Patio
  • Stereo System
  • VCR
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • 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
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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...
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From
$750
Per Night
1 / 26
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Annapolis
6 Bedrooms, 5 Bathrooms, Sleeps 13
Bookings
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Amenities & Details
  • Dishwasher
  • Air Conditioning
  • Washer
  • DVD Player
  • VCR
  • Parking
  • Microwave
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • 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
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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...
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From
$400
Per Night
1 / 30
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Annapolis
4 Bedrooms, 3 Bathrooms, Sleeps 9
Bookings
Details Reviews (2) Make Inquiry Similar Properties
Amenities & Details
  • Refrigerator
  • Stereo System
  • Stove
  • Washer
  • Grill
  • Fireplace
  • Air Conditioning
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • Smoking allowed
  • 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
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From
$200
Per Night
1 / 23
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Baltimore
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
Details Reviews (1) Make Inquiry Similar Properties
Amenities & Details
  • Microwave
  • Dryer
  • Deck
  • Ceiling Fans
  • Satellite TV
  • Parking
  • Stove
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • 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
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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...
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From
$275
Per Night
1 / 53
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Baltimore
2 Bedrooms, 3 Bathrooms, Sleeps 6
Bookings
Details Reviews (3) Make Inquiry Similar Properties
Amenities & Details
  • Grill
  • Patio
  • Washer
  • Hot Tub
  • Fireplace
  • Canoe
  • Dishwasher
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
************ RATE INCLUDES PLENTY OF ONSITE ACTIVITIES AND AMENITIES! ************** ****** THIS HOME IS A 2 BEDROOM PLUS A STUDIO APARTMENT UNIT IN LOWER LEVEL + 2.5 BATHS ****** PLEASE NOTE THAT RATES FOR PERIODS OF SPECIAL EVENTS LIKE THE STADIUM GAMES, ETC. ARE NOT NOTED HERE. CONTACT OWNER... View all property information
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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...
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From
$120
Per Night
1 / 7
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Baltimore
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (4) Make Inquiry Similar Properties
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • 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
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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...
5 of 5 stars Reviewed July 2, 2014
First and foremost, Sussane and Joe were the best host I have ever met! They were very nice and helpful! I couldn't ask for more accommodating hosts! The apartment is great...
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From
$379
Per Night
1 / 21
Payment Protection
Baltimore
5 Bedrooms, 6 Bathrooms, Sleeps 8
Bookings
Details Reviews (1) Make Inquiry Similar Properties
Amenities & Details
  • Refrigerator
  • Washer
  • Patio
  • DVD Player
  • Parking
  • Dishwasher
  • Microwave
  • Stove
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Built in the 1920s, this unique house retains its original charm, it is spacious and creatively painted, with hardwood floors throughout. Fully furnished and decorated with artwork, rugs and antiques. 1 king bedroom and 3 additional bedrooms with comfortable queen size beds, linens, dishes,... View all property information
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4 of 5 stars Reviewed July 1, 2014
This house is a no shoes house with lots of space and rooms for a big family as mine. We enjoyed the amenities, but the internet service was limited, which we did not mined. The...
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From
$280
Per Night
1 / 3
Payment Protection
Annapolis
4 Bedrooms, 4 Bathrooms, Sleeps 8
Details Make Inquiry Similar Properties
Amenities & Details
  • Towels Provided
  • Balcony
  • Air Conditioning
  • Garden or Yard
  • Central Heating
  • Local Guides/Maps
  • Ceiling Fans
  • Linens Provided
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Unique Bed and Breakfast One of the oldest residences in Annapolis with all modern amenities. Best Breakfast! Perfect for USNA and St. John's families Wonderful hosts! View all property information
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From
$275
Per Night
1 / 11
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Baltimore
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Make Inquiry Similar Properties
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
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
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From
$140
Per Night
1 / 6
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Baltimore
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Inquiry Similar Properties
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • 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
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From
$150
Per Night
1 / 18
Payment Protection
Annapolis
4 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
Details Make Inquiry Similar Properties
Amenities & Details
  • Refrigerator
  • Parking
  • Dryer
  • VCR
  • Stove
  • Washer
  • DVD Player
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • Smoking allowed
  • Elder access
  • x
About this property
The perfect retreat for a family visiting Annapolis on vacation or for visiting your Johnny at St. John's 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... View all property information
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From
$120
Per Night
1 / 4
Payment Protection
Baltimore
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Make Inquiry Similar Properties
Amenities & Details
  • Dishwasher
  • Local Guides/Maps
  • Soap/Shampoo...
  • Microwave
  • Stove
  • Central Heating
  • Refrigerator
  • Internet Access
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • 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
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From
$299
Per Night
1 / 3
Payment Protection
Baltimore
4 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry Similar Properties
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • 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
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From
$170
Per Night
1 / 14
Payment Protection
Annapolis
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Make Inquiry Similar Properties
Amenities & Details
  • Stove
  • Dryer
  • Refrigerator
  • Dishwasher
  • Microwave
  • Patio
  • Ceiling Fans
  • Satellite TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
PLEASE CONTACT US BEFORE BOOKING FOR USNA GRADUATION and BOAT SHOWS (Rates May Vary) PLEASE NOTE WE ARE NOT TAKING RESERVATIONS FOR USNA GRADUATION 2015-2016 Large 1 BR 1 BA apartment with den/study (single pull-out daybed available), large and bright living room with pull-out sofa, and three... View all property information
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From
$400
Per Night
1 / 23
Payment Protection
Annapolis
2 Bedrooms, 2 Bathrooms, Sleeps 10
Booking
Details Make Inquiry Similar Properties
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • 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
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From
$250
Per Night
1 / 20
Payment Protection
Annapolis
3 Bedrooms, 1 Bathroom, Sleeps 7
Details Make Inquiry Similar Properties
Amenities & Details
  • Refrigerator
  • Hot Tub
  • Stove
  • Fireplace
  • Garage
  • Washer
  • Parking
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Charming 3BR 1BA cape cod is 1 1/2 miles from City Dock and USNA. Enjoy the large back yard with two-level patio, hot tub and fire pit. Master bedroom has king bed. Second bedroom has a queen sized bed. Air mattress available in office for third bedroom. Additional queen air mattress available... View all property information
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From
$169
Per Night
1 / 4
Payment Protection
Annapolis
3 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
Details Reviews (2) Make Inquiry Similar Properties
Amenities & Details
  • Dryer
  • DVD Player
  • Dishwasher
  • Washer
  • VCR
  • Ceiling Fans
  • Refrigerator
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Large, open third floor condominium with cathedral ceilings. Large master bedroom has queen bed. 2nd bedroom has twin beds. Large loft has queen size bed. Although the condo can accommodate 6 for sleeping, I will rent only to parties of 4 or fewer. Dining room can seat 8 + Washer and Dryer,... View all property information
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5 of 5 stars Reviewed June 29, 2014
We really enjoyed our stay at your condo. It was roomy and felt like home. It is in a very nice condo community which was very quiet. It was nice being able to cook and see into...
5 of 5 stars Reviewed November 12, 2013
My family of four stayed there for the weekend. We were there to watch the Navy-Hawaii football game. We could not find any hotel rooms in/around Annapolis that could host a...
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From
$200
Per Night
1 / 7
Payment Protection
Baltimore
5 Bedrooms, 5 Bathrooms, Sleeps 6
Bookings
Details Reviews (3) Make Inquiry Similar Properties
Amenities & Details
  • Parking
  • Grill
  • Safe
  • Microwave
  • Refrigerator
  • Dishwasher
  • Washer
  • Garage
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • 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
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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...
5 of 5 stars Reviewed August 3, 2014
Nice old home with lots of character, we could tell that there is a lot of love put in the house. It was only a 10 minute walk from Johns Hopkins, which was why we were there...
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From
$400
Per Night
1 / 7
Payment Protection
Annapolis
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
Details Make Inquiry Similar Properties
Amenities & Details
  • Microwave
  • DVD Player
  • Stereo System
  • Grill
  • Dishwasher
  • Fireplace
  • Patio
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • 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
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From
$1,500
Per Night
1 / 15
Payment Protection
Annapolis
4 Bedrooms, 4 Bathrooms, Sleeps 10
Bookings
Details Make Inquiry Similar Properties
Amenities & Details
  • Stove
  • Dishwasher
  • Microwave
  • Refrigerator
  • Garage
  • Patio
  • Dryer
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Striking and dramatic 8700 - 9000 sf contemporary, new loft style renovation and building addition with exposed structure and mechanical systems that serves as the architect - owner's live-work getaway. The main house has a 4 stop elevator, 2 car garage, master bdrm and bath suite, 3 additional... View all property information
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From
$300
Per Night
1 / 9
Payment Protection
Annapolis
1 Bedroom, 1 Bathroom, Sleeps 2
Details Make Inquiry Similar Properties
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • Smoking allowed
  • Elder access
  • x
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
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From
$500
Per Night
1 / 11
Payment Protection
Annapolis
1 Bedroom, 2 Bathrooms, Sleeps 4
Details Make Inquiry Similar Properties
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
This is the newly renovated 3-story open plan live-work unit that is connected to the main house that is similarly titled as the main house (1) and the studio apartment (2) - not included with this listing. Striking and dramatic 1500 - 1600 sf contemporary, open plan loft style renovation with a... View all property information
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From
$480
Per Night
1 / 8
Payment Protection
Baltimore
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Make Inquiry Similar Properties
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
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
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From
$115
Per Night
1 / 5
Payment Protection
Galena
2 Bedrooms, 1 Bathroom, Sleeps 5
Details Make Inquiry Similar Properties
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • ?
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
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From
$250
Per Night
1 / 11
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Baltimore
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
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Amenities & Details
  • Garage
  • Refrigerator
  • Hot Tub
  • Microwave
  • Dryer
  • Grill
  • Parking
  • Air Conditioning
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • Smoking allowed
  • 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
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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...
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From
$275
Per Night
1 / 6
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Baltimore
2 Bedrooms, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Deck
  • Parking
  • Refrigerator
  • Washer
  • Microwave
  • Pool
  • Porch
  • Safe
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • 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
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From
$200
Per Night
1 / 18
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Baltimore
3 Bedrooms, 1 Bathroom, Sleeps 8
Bookings
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Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • 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
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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...
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From
$325
Per Night
1 / 21
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Baltimore
3 Bedrooms, 2 Bathrooms, Sleeps 9
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Amenities & Details
  • Stereo System
  • Dryer
  • Stove
  • Parking
  • Dishwasher
  • Ceiling Fans
  • Grill
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • 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
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From
$300
Per Night
1 / 8
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Baltimore
3 Bedrooms, 2 Bathrooms, Sleeps 7
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Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
This is a 100 year old house near Catonsville, MD. It's near a national cemetery and was most likely the house the stone worker for the local cemeteries owned. As such, the stone work of this house is some of the best in Baltimore. The house has an older stone exterior. The inside floors are all... View all property information
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$250
Per Night
1 / 15
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Rock Hall
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • Smoking allowed
  • 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
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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...
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From
$180
Per Night
1 / 12
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Rock Hall
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
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Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • 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
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From
$700
Per Night
1 / 6
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Annapolis
5 Bedrooms, 6 Bathrooms, Sleeps 12
Booking
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Amenities & Details
  • DVD Player
  • Microwave
  • Patio
  • Fireplace
  • Refrigerator
  • Washer
  • Grill
  • Garage
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
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
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From
$695
Per Night
1 / 25
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Annapolis
5 Bedrooms, 3 Bathrooms, Sleeps 21
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Amenities & Details
  • Hot Tub
  • DVD Player
  • Washer
  • Canoe
  • Microwave
  • Refrigerator
  • Dishwasher
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • 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 2014) offer gourmet kitchen with new stainless steel appliances, a second full kitchen in garden... View all property information
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From
$209
Per Night
1 / 11
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Stevensville
2 Bedrooms, 1 Bathroom, Sleeps 6
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Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
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
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$180
Per Night
1 / 21
Chester
4 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Refrigerator
  • Microwave
  • Dishwasher
  • Patio
  • Grill
  • Canoe
  • Washer
  • Fireplace
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Waterfront Rancher on 3 acres, centrally located between Washington DC, St. Michaels, Annapolis, and Baltimore. 4 Bed/2 Bath home with central air sleeps 8. This home has been in our family for over 50 years and is a special place. Over the years there have been many updates to the home. The... View all property information
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5 of 5 stars Reviewed July 29, 2013
First I would like to say thanks, to Harry, and Scott. They were the best host, I've encountered. They have a property, they can be proud of. The house was just excellent. The...
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From
$295
Per Night
1 / 22
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Baltimore
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
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Amenities & Details
  • DVD Player
  • Safe
  • Stove
  • Dishwasher
  • Dryer
  • Washer
  • Grill
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
This lovingly restored townhouse in Baltimore's exciting Fell's Point historic district has been modernized and tastefully furnished. Lancaster House is available as short-term rental accommodations. While the house still retains the character of a 200+ year old home, the living space has been... View all property information
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5 of 5 stars Reviewed August 19, 2012
My friends & I stayed in the Lancaster house a few weeks ago, when in town to see the Orioles play. We go to a different city every year, to see a different ballclub/stadium, and...
5 of 5 stars Reviewed May 21, 2012
I stayed for 11 nights and never regretted. This rental is pure Baltimore: classic row/town house on quiet street but 5 minutes from all you can want. Yes, the stair case is very...
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From
$299
Per Night
1 / 12
Perryville
5 Bedrooms, 2 Bathrooms, Sleeps 13
Details Reviews (1) Make Inquiry Similar Properties
Amenities & Details
  • Grill
  • Stereo System
  • Dishwasher
  • Refrigerator
  • Ceiling Fans
  • Stove
  • DVD Player
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
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
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From
$170
Per Night
1 / 28
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Baltimore
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (24) Make Inquiry Similar Properties
Amenities & Details
  • Microwave
  • Dryer
  • Refrigerator
  • Safe
  • Washer
  • Stove
  • Dishwasher
  • Air Conditioning
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
This is a fully appointed in-laws apartment on the third floor of an owner occupied guest house. You have the option of reserving only one bedroom for up to two guests, or three bedrooms for up to 6 guests. CURRENT RATES: - 1 BEDROOM, 1 BATH CORPORATE APARTMENT (2 guest max): $170 per night. - THE... View all property information
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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...
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From
$171
Per Night
1 / 28
Centreville
4 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (3) Make Inquiry Similar Properties
Amenities & Details
  • Microwave
  • Fireplace
  • Grill
  • Dishwasher
  • Stove
  • Parking
  • Patio
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This house is on the former estate of John Raskob, builder of the Empire State Building. The four-bedroom, two-bath house is one of seven that Raskob built for his farm employees. Now it has its own dock and swimming pool fronting on Grove Creek, with access to the Chester River and Chesapeake... View all property information
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From
$250
Per Night
1 / 23
Annapolis
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry Similar Properties
Amenities & Details
  • Washer
  • DVD Player
  • Grill
  • Microwave
  • Stove
  • Dryer
  • Garage
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • 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
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From
$150
Per Night
1 / 13
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Baltimore
2 Bedrooms, 1 Bathroom, Sleeps 6
Details Reviews (3) Make Inquiry Similar Properties
Amenities & Details
  • Patio
  • Water Views
  • Microwave
  • Internet Access
  • Grill
  • Balcony
  • Waterfront
  • Satellite TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
The most unique vacation rental you'll find in Baltimore! Stay waterfront in Fells Point on the fun and funky houseboat Delphinus. It's your home away from home on the water! Our houseboat is fully furnished with a well equipped kitchen, full size refrigerator, cooktop, microwave, and coffeemaker.... View all property information
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5 of 5 stars Reviewed March 31, 2014
From check-in to check-out our weekend getaway was very smooth and we had very detailed instructions. The place was very clean and delightful. We enjoyed our stay & had a...
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