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 16 Rentals in the Chestertown Area
    loading...
    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
    $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
    $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
    • Waterfront
    • Air Conditioning
    • Fireplace
    • Water Views
    • DVD Player
    • Deck
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • 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
    From
    $190
    / Night
    Payment Protection
    View Details
    1 / 10
    Chestertown
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Washer
    • Wi-Fi
    • Housekeeping...
    • Satellite TV
    • Grill
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Our Victorian cottage, built in the 1880s and upgraded to more modern standards, offers the best of both worlds: A bit of a rural feel, with a fenced-in side yard and back yard, a lovely porch swing, and ... easy strolling distance to the downtown historic Chestertown. Did you know that the... View all property information
    Make Inquiry
    Location Information
    Chestertown, Maryland 21620

    The following rentals are within 20 miles of Chestertown, Maryland.

    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
    • 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
    Make Inquiry
    Location Information
    Stevensville, Kent Island 21666
    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
    • Shared Outdoor Pool...
    • Stereo System
    • Satellite TV
    • Washer
    • DVD Player
    • Patio
    • Dryer
    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
    Make Inquiry
    Location Information
    Rock Hall, Maryland 21661
    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
    • 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
    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
    $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
    • 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
    Make Inquiry
    Location Information
    Rock Hall, Maryland 21661
    From
    $115
    / Night
    Payment Protection
    View Details
    1 / 5
    Galena
    2 Bedrooms / 1 Bathroom / Sleeps 5
    Overview Make Inquiry
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • 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
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    From
    $980
    / Night
    Payment Protection
    View Details
    1 / 11
    Dundalk
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    traveler have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Private Yard
    • Safe
    • Towels Provided
    • Wi-Fi
    • Highchair
    • Air Conditioning
    • Linens Provided
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    You will really comfortable by chosing this nearly-new, custom-designed colonial that has a distinct contemporary flair - decorated in gorgeous, neutral d~cor!!2 acres of land - soaring ceilings, gleaming wood floors - and a family room/kitchen design that everyone wants: gourmet kitchen... View all property information
    Make Inquiry
    Location Information
    Dundalk, Maryland DUNDALK
    From
    $235
    / Night
    Payment Protection
    View Details
    1 / 9
    Rock Hall
    3 Bedrooms / 1 Bathroom / Sleeps 8
    traveler have booked this property
    Overview Make Inquiry
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Washer
    • Patio
    • Refrigerator
    • Grill
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • 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
    $280
    / Night
    View Details
    1 / 21
    5 of 5 stars (2) Excellent
    Chester
    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • Satellite TV
    • DVD Player
    • Private Fishing...
    • Waterfront
    • Air Conditioning
    • Water Views
    • Fireplace
    • Internet Access
    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
    Make Inquiry
    Location Information
    Chester, Kent Island 21619
    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...
    See all reviews
    From
    $375
    / Night
    View Details
    1 / 37
    Chester
    4 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • Satellite TV
    • Hot Tub
    • Deck
    • Water Views
    • Internet Access
    • Waterfront
    • Stereo System
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Swan Cove Condominiums at Kent Narrows(#49064) with private beach and views of the Chesapeake bay! - Brand new luxury condominium with 3000 sq ft, 4 bedrooms, 3 ½ bathrooms, one large family room with open kitchen, one large sunny living room and dinning area. There are 2 king size bed, 2 queen... View all property information
    Make Inquiry
    Location Information
    Chester, Kent Island 21619
    From
    $550
    / Night
    View Details
    1 / 23
    Stevensville
    4 Bedrooms / 4 Bathrooms / Sleeps 14
    Overview Make Inquiry
    Amenities & Details
    • Deck
    • Stereo System
    • Boat Available
    • Air Conditioning
    • Satellite TV
    • Internet Access
    • Waterfront
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    View Details
    1 / 12
    Grasonville
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • Internet Access
    • Hot Tub
    • Satellite TV
    • Waterfront
    • Boat Available
    • Air Conditioning
    • DVD Player
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Welcome to Baydreams vacation home, a unique waterfront vacation home situated near the Kent Narrows in Queen Anne's County, on the Eastern Shore of Maryland. Book the comfort and convenience of a 4 bedroom 3 bath home offering a unique lodging to the discriminating traveler that other... View all property information
    Make Inquiry
    Location Information
    Grasonville, Maryland 21638