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Vacation Rentals in Chestertown, MD

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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 / 14
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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 / 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 / 14
    4.5 of 5 bubbles (3) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • Waterfront
    • Air Conditioning
    • Grill
    • DVD Player
    • Washer
    • Patio
    • Satellite TV
    • Wi-Fi
    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 / 11
    4 of 5 bubbles (2) Very good
    3 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    A 3 bedroom house on the Chester River with amazing sunsets over the dock. Fully equipped, with central air conditioning, dishwasher, washer, dryer and parking - also free use of kayaks to enjoy the Chester River. An ideal property for those dropping off, picking up, or just visiting a student at... View all property information
    Location Information
    Chestertown, Maryland 21620
    3 of 5 bubbles Reviewed August 15, 2015
    The sunsets are magnificent. The house is comfy, but showing some deferred maintenance like grass growing from the gutters, green stuff on the exterior, landscaping so very...
    5 of 5 bubbles Reviewed August 29, 2014
    what a beautiful area of md. to stay at for an relaxing get away.the beautiful sun sets and sunrise.
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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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