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Holiday Rentals near Chester River Wine & Cheese Co.

117 S Cross St, Chestertown, Maryland 21620-1513
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    Don't let other travellers get your favourite Chestertown area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 6 Rentals in Chestertown
    Cozy & Spacious Chestertown Home1 / 28
    (5)Excellent
    Chestertown
    0.7 miles from Chester River Wine & Cheese Co.
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Belle Rose Cottage at Victory Farm (Pet Friendly!)1 / 17
    (3)Excellent
    Chestertown
    3.0 miles from Chester River Wine & Cheese Co.
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Chester River House with Views1 / 11
    (4)Very good
    Chestertown
    1.0 miles from Chester River Wine & Cheese Co.
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Cottage On Kent1 / 7
    (1)Excellent
    Chestertown
    0.4 miles from Chester River Wine & Cheese Co.
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Washer
    • Central Heating
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    I found this charming cottage to be perfect; Lorraine and David have thought of everything to make a visit to Chestertown delightful, comfortable and easy. The cottage is...
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    About this property
    Cottage On Kent is a guest cottage within walking distance to downtown, the Chester River and Washington College. It has one bedroom with a queen size bed, a full kitchen, a spacious bathroom, a cozy living room, off-street parking and access to an outside sitting area. The Cottage is...
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    Location Information
    Chestertown, Maryland
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Cozy Apartment in Chestertown1 / 7
    (1)Excellent
    Chestertown
    0.2 miles from Chester River Wine & Cheese Co.
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 May 2017
    This first floor apartment is cozy, sweet, and convenient to everything downtown. A quick 2 block walk brings you to restaurants, shops, galleries, the Farmer's Market on...
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    About this property
    A delightful one-bedroom apartment located in historic Chestertown. Close to Washington College & Heron Point. Apartment accommodates 2 guests. It is the perfect place for enjoying this historic, artistic town on Maryland's Eastern Shore. The space includes kitchen/living room combo, bedroom with...
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    Location Information
    Chestertown, Maryland
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Charming Apartment in Historic Chestertown, MD1 / 10
    (7)Excellent
    Chestertown
    0.2 miles from Chester River Wine & Cheese Co.
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Terrace
    • Balcony
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 May 2017
    This is a lovely upstairs apartment with a super comfy bed, great shower, and everything you would want or need for an easy stay. The cupboards are stocked, you can cook if you...
    Reviewed 27 August 2015
    Absolutely the best deal for me in Chestertown. Came back to visit family and friends, and luckily this place was available. Home away from home, roomy, and I was able to work...
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    About this property
    This artistic, light-filled one-bedroom apartment is located in historic Chestertown, MD. The space includes kitchen/living room combo, bedroom with queen size bed, bathroom with shower and tub. An outdoor deck with cafe table and chairs is a nice place to sit on a sunny day. It is perfect for a...
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    Location Information
    Chestertown, Maryland
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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