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Vacation Rentals in Chestertown, MD and nearby

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    15 Vacation Rentals in Chestertown
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    From
    $145
    / Night
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    1 / 11
    5 of 5 stars (1) Excellent
    Chestertown
    3 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
    Overview Reviews (1)
    From
    $99
    / Night
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    1 / 10
    5 of 5 stars (5) Excellent
    Overview Reviews (5)
    From
    $120
    / Night
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    1 / 28
    5 of 5 stars (2) Excellent
    Chestertown
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Overview Reviews (2)
    From
    $295
    / Night
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    1 / 12
    4.5 of 5 stars (3) Very good
    Overview Reviews (3)

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

    From
    $235
    / Night
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    1 / 9
    Rock Hall
    3 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    From
    $209
    / Night
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    1 / 11
    Stevensville
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    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
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    From
    $250
    / Night
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    1 / 17
    5 of 5 stars (3) Excellent
    Rock Hall
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
    Overview Reviews (3)
    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
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    From
    $115
    / Night
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    1 / 5
    Galena
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
    Overview
    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
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    From
    $250
    / Night
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    1 / 15
    4 of 5 stars (2) Very good
    Rock Hall
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    Overview Reviews (2)
    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
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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
    / Night
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    1 / 12
    Rock Hall
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Overview
    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
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    From
    $280
    / Night
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    1 / 21
    5 of 5 stars (2) Excellent
    Chester
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Overview Reviews (2)
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Private Fishing...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • 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
    $300
    / Night
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    1 / 30
    4.5 of 5 stars (3) Very good
    Centreville
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Overview Reviews (3)
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • 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
    $575
    / Night
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    1 / 23
    Stevensville
    4 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
    Overview
    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
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    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
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    From
    $450
    / Night
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    1 / 12
    Grasonville
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
    Overview
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • 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
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    From
    $375
    / Night
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    1 / 37
    Chester
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
    Overview
    Amenities & Details
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • 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
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