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.

Holiday Homes and Apartments Kennedyville, 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.
dd/mm/yyyy dd/mm/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 Payment Protection.Learn more
    Show Prices
    Change Dates
    Price
    per night
    |||
    |||
    $0
    $296 Average
    $1,000+
    Bedrooms
    Any
    Amenities
    Any
    Payment
    Book Online
    View Map
    More filters
    loading...
    Don't let other travellers get your favourite Kennedyville area holiday rental. You're so close to securing your perfect getaway. Book today.

    The following rentals are within 40 kilometres of Kennedyville, Maryland.

    1 / 11
    4 of 5 stars (2) Very good
    Chestertown
    3 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    1 / 10
    5 of 5 stars (6) Excellent
    Chestertown
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    1 / 21
    5 of 5 stars (1) Excellent
    Chestertown
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    1 / 28
    5 of 5 stars (2) Excellent
    Chestertown
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Porch
    • Grill
    • Patio
    • Parking
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This cozy one-bedroom house is a wonderful spot for a weekend getaway or as a base to discover the culture, history and cuisine of Maryland's Eastern Shore. Enjoy nature, birds - bald eagles, ospreys, blue herons - stunning sunsets and more by the bay. The one-bedroom house includes full kitchen,... View all property information
    Location Information
    Chestertown, Maryland 21620
    5 of 5 stars Reviewed 10 June 2014
    My husband and I were lucky enough to stay in a charming little guest house on the Bay (Tolchester area of Chestertown, MD). House is almost right on the water, very clean, very...
    5 of 5 stars Reviewed 10 June 2014
    I stayed at Francesca's lovely Bayview cottage on the Chesapeake Bay in Tolchester, Maryland this weekend. The cottage is delightful, with porches on three sides, comfy beds, and...
    See all reviews
    Chestertown
    4 Bedrooms, 8 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Waterfront
    • DVD Player
    • Washer
    • Ocean Views
    • Patio
    • Grill
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This gorgeous home is located directly on the Chester River in Chestertown, Md, on the Eastern shore. There are 5 bedrooms, one down and four on the second floor. On the main floor there is a great room that is part kitchen, part TV area and part dining room. Off of this room is a lovely living... View all property information
    Location Information
    Chestertown, Maryland 21620
    Rock Hall
    3 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Washer
    • Grill
    • Parking
    • Porch
    • Patio
    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
    Location Information
    Rock Hall, Maryland 21661
    1 / 22
    4.5 of 5 stars (3) Very good
    Chestertown
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Waterfront
    • Air Conditioning
    • DVD Player
    • Satellite TV
    • Washer
    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
    Location Information
    Chestertown, Maryland 21620
    3 of 5 stars Reviewed 18 October 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.
    5 of 5 stars Reviewed 28 May 2013
    This rental has everything you could possibly need. A public boat launch a 1/4 mile or less from the house. Kayaks and a large amount of water to explore. A gorgeous 10 mile drive...
    See all reviews
    Chestertown
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other traveller has booked this property
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Patio
    • Washer
    • Wi-Fi
    • Housekeeping...
    • Satellite TV
    • Balcony
    • Grill
    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
    Location Information
    Chestertown, Maryland 21620
    1 / 15
    4 of 5 stars (2) Very good
    Rock Hall
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    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
    Location Information
    Rock Hall, Maryland 21661
    4 of 5 stars 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...
    4 of 5 stars 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 no...
    See all reviews
    Rock Hall
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
    Show Prices
    Payment Protection
    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
    Location Information
    Rock Hall, Maryland 21661
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    1 / 17
    5 of 5 stars (3) Excellent
    Rock Hall
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Shared Outdoor Pool...
    • Washer
    • Satellite TV
    • Patio
    • DVD Player
    • Porch
    • Grill
    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
    Location Information
    Rock Hall, Maryland 21661
    5 of 5 stars Reviewed 20 April 2012
    Great house in a nice location near Marinas, walking distance to restaurants and charming town of Rock Hall. Great place to relax or to take a bike ride. Plenty of sleeping room...
    5 of 5 stars Reviewed 19 April 2012
    We have stayed at this property several times and are planning on booking more time there. The house is great, I think one of the only 3 bedroom 2 bathroom rentals in town. It's a...
    See all reviews
    North East
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Parking
    • Satellite TV
    • Grill
    • Waterfront
    • Washer
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Come vacation in this brand-new home in beautiful Elk Neck and you will be glad you did! It is definitely a most gorgeous location and very peaceful, set back in the woods along the river. Elk Neck is approximately eight miles south of the town of North East, MD where there are many neat little... View all property information
    Location Information
    North East, Maryland 21901
    Galena
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
    Show Prices
    Payment Protection
    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
    Location Information
    Galena, Maryland 21625
    1 / 12
    5 of 5 stars (2) Excellent
    Perryville
    5 Bedrooms, 2 Bathrooms, Sleeps 13 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Waterfront
    • Satellite TV
    • Balcony
    • Internet Access
    • Washer
    • Grill
    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
    Location Information
    Perryville, Maryland 21903
    5 of 5 stars Reviewed 6 August 2015
    The location can't be beat. We had 3 families with teenagers for a lacrosse tournament. We entertained the whole team on the 4th. The house was a perfect fit for our needs...
    5 of 5 stars Reviewed 19 December 2011
    Couldn't ask for a better host.I was made to feel like it was my own home.It's such a charming house.Beautiful view's enjoyed watching the eagles.Looking out across the...
    See all reviews