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.

Elder Access Holiday Rentals in Chestertown

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.
Check In Check Out
    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}
    View Map
    Price
    per night
    $348 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Don't let other travellers get your favourite Chestertown area holiday rental. You're so close to securing your perfect getaway. Book today.
    7 Matching Rentals in the Chestertown AreaView all 15 rentals
    Sort by:
    Default
    Chester River House with Views1 / 11
    (2)Very good
    Chestertown
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Bayview by Chesapeake Bay1 / 28
    (3)Excellent
    Chestertown
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Gorgeous Home on Chester River1 / 16
    (1)Excellent
    Chestertown
    4 Bedrooms, 9 Bathrooms, Sleeps 8 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    The following rentals are within 30 kilometres of Chestertown.
    Waterfront Cottage at Spring Cove1 / 15
    (2)Very good
    Rock Hall
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 September 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...
    Reviewed 19 August 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...
    See all reviews
    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
    Location Information
    Rock Hall, Maryland 21661
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    * 3 Bedroom Rental House in Historic Rock Hall MD1 / 17
    (3)Excellent
    Rock Hall
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Satellite TV
    • Patio
    • DVD Player
    • Porch
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Location Information
    Rock Hall, Maryland 21661
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Enquiry
    Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets)1 / 21
    (3)Excellent
    Chester
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Patio
    • Satellite TV
    • Waterfront
    • Wi-Fi
    • Washer
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 January 2016
    We have stayed in this home several times and will return in July. It is a wonderful house with a private master suite at one end, two bedrooms with a 2nd bath at the other.The...
    Reviewed 29 July 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...
    See all reviews
    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
    Location Information
    Chester, Kent Island 21619
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Sailors Crossing1 / 12
    (2)Excellent
    Rock Hall
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Central Heating
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 days ago
    House was great. Plenty of room to hang out and have fun with a large group and the grill was a plus. Just down the street from an awesome restaurant on the water and a short...
    Reviewed 2 weeks ago
    Stayed here in July...not one bad thing to say! Beautiful, charming, spacious, comfy home. Had an amazing relaxing weekend. Close to everything. Can't wait to go again!!!
    See all reviews
    About this property
    Sailors Crossing is a 3 bedroom, 2 bath home located in the heart of Rock Hall. The dining room seats 6 and the kitchen is roomy enough for several cooks and helpers. If it's crab you're after, the screened porch provides enough room for the group or take the feast out to the backyard, there's...
    View all property information
    Location Information
    Rock Hall, Maryland 21661
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
    Make Enquiry
    Save time - get the best Chestertown rentals sent straight to your email!
    Get the List
    List your property
    Owner log in