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Vacation Rentals in Chestertown, MD

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    1 / 28
    5 of 5 bubbles (3) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 11
    4 of 5 bubbles (2) Very good
    3 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    1 / 10
    5 of 5 bubbles (6) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    1 / 16
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 9 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Waterfront
    • DVD Player
    • Washer
    • Ocean Views
    • Patio
    • Grill
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    5 of 5 bubbles Reviewed June 7, 2016
    Our group - kids and adults - thoroughly enjoyed our stay here. We loved being right on the water and enjoyed the beautiful view. The house was very clean and spacious. It was...
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    1 / 21
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Parking
    • Outdoor Dining Area
    • Private Yard
    • Wi-Fi
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Modern, Cozy 2-Bedroom Cottage with sleeping loft. Views of the Chesapeake Bay from wraparound deck. Perfect destination for families & friends for Bay & Sunsets. Located in the scenic, serene environs of the Eastern Shore of Maryland in Tolchester. The two-bedroom house with sleeping loft... View all property information
    Location Information
    Chestertown, Maryland 21620
    5 of 5 bubbles Reviewed September 24, 2015
    I took my mother here for a getaway birthday weekend. I wanted somewhere we could relax but also be inspired by our surroundings. This quaint cottage was perfect. Nestled close to...
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    1 / 22
    4.5 of 5 bubbles (3) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Grill
    • Waterfront
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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 bubbles Reviewed October 17, 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.
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    1 / 14
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Private Yard
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Our home is located within short walking distances from Washington College(three blocks), the riverfront(four blocks), the farmer's market(one block, downtown shopping, bakery, banks, government buildings ( one to three blocks) . It is fully furnished and equipped. There is ample on street parking,... View all property information
    Location Information
    Chestertown, Maryland 21620
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