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Holiday Rentals in Chestertown

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    All 16 Rentals in Chestertown
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    Cozy & Spacious Chestertown Home1 / 28
    (5)Excellent
    Chestertown
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Retreat at a quiet, water front cottage1 / 14
    (3)Very good
    Chestertown
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Chester River House with Views1 / 11
    (4)Very good
    Chestertown
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Gorgeous Home on Chester River1 / 16
    (2)Very good
    Chestertown
    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
    Kid friendly
    Smoking allowed
    Reviewed 13 February 2018
    This is a lovely , comfortable home. We enjoyed our stay very much and would definitely rent the house again. There were a few glitches due to the house having been closed up...
    Reviewed 7 June 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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    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...
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    Chestertown, Maryland 21620
    Holiday Rental House - 4 Bedrooms, 9 Bathrooms, Sleeps 8
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    Belle Rose Cottage at Victory Farm (Pet Friendly!)1 / 17
    (3)Excellent
    Chestertown
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Parking
    • Air Conditioning
    • Private Garden
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 June 2018
    This is not my first stay at the cottage and I was stoked to be there. My wife and I had more than the space we needed as well as things we needed in the kitchen and laundry in...
    Reviewed 16 January 2018
    This cottage is a little piece of heaven. Everything you need for a short- or long-term stay is right at your fingertips: a full-sized kitchen, living room, bedroom, and a...
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    About this property
    Nestled behind the main house with a fenced garden, the cottage is a cozy respite after a busy day site seeing or visiting with local friends. Relax and discover the culture, history, nature, and cuisines of Maryland's Eastern Shore. Perfect for folks traveling with a dog or two. Short or long term...
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    Chestertown, Maryland 21620
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Cottage On Kent1 / 7
    (1)Excellent
    Chestertown
    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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    Chestertown, Maryland 21620
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Charming Apartment in Historic Chestertown, MD1 / 10
    (7)Excellent
    Chestertown
    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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    Chestertown, Maryland 21620
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Sunview Cottage on Chesapeake Bay1 / 22
    (1)Excellent
    Chestertown
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Parking
    • Outdoor Dining Area
    • Private Garden
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 September 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...
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    About this property
    Modern, Cozy 2-Bedroom Cottage with sleeping loft. Views of the Chesapeake Bay from house and wraparound deck. Perfect destination for a couples getaway, family trip or friends gathering to enjoy the Bay & Sunsets. Located in the scenic, serene environs of the Eastern Shore of Maryland in...
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    Chestertown, Maryland 21620
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Cozy Apartment in Chestertown1 / 7
    (1)Excellent
    Chestertown
    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 21620
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    The following rentals are within 25 kilometers of Chestertown.
    Waterfront House, Eastern Shore Chesapeake Bay1 / 34
    (22)Excellent
    Centreville
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Washer
    • Air Conditioning
    • Porch
    • Cable/satellite TV
    • Grill
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We welcome your inquiries and would be glad to answer any questions you have before booking. In response to inquiries and booking requests, we will send you our standard rental agreement for your information and approval. This house is on the estate of John Raskob, builder of the Empire State...
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    Location Information
    Centreville, Maryland 21617
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Summer House1 / 10
    (1)Excellent
    Rock Hall
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Grill
    • Parking
    • Porch
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 September 2018
    The location is peaceful and about 2 blocks from the water. The "Summer House" was clean and set up well for guests with plenty of linens and towels. We had 8 people...
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    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...
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    Location Information
    Rock Hall, Maryland 21661
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    Sailors Crossing1 / 12
    (3)Excellent
    Rock Hall
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Patio
    • Central Heating
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 September 2017
    Beautiful home with many amenities, clean and comfortable. Awesome screened-in porch, great place to enjoy your morning coffee. Community park right behind home with tennis...
    Reviewed 15 August 2017
    House was great. Plenty of room to hang out and have fun with a large group and the grill was a plus. Just down the street from an awesome restaurant on the water and a short...
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    About this property
    Sailors Crossing is a 3 bedroom, 2 bath home located in the heart of Rock Hall. Parking is limited to 3 cars. The dining room seats 6 and the kitchen is roomy enough for several cooks and helpers. If it's crab you're after, the screened porch provides enough room for the group or take the feast out...
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    Location Information
    Rock Hall, Maryland 21661
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Rock Hall
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Parking
    • Air Conditioning
    • Washer
    • Grill
    • Private Garden
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on one of the prettiest streets in Rock Hall, the Bay Cottage offers 2 bedrooms and 1 full bathroom. A fully equipped kitchen, gas grill and outdoor seating pulls the family together for mealtimes or enjoy our local restaurants which are just a short walk. Pets are welcomed on this fenced...
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    Location Information
    Rock Hall, Maryland 21661
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Still Pond
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Central Heating
    • Washer
    • Terrace
    • Patio
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious room w old pine floors, comes with semi-private bathroom, breakfast and some meals provided, in a charming Victorian in delightful town, half acre lot and shared use of rooms. Out and out close for 15 scenic launching areas for boating. Less than 5 mins to spectacular sunsets at Betterton....
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    Still Pond, Maryland 21667
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Peace and Quiet in a Delightful Victorian1 / 37
    (2)Very good
    Still Pond
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Wi-Fi
    • Patio
    • Private Garden
    • Washer
    • Parking
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 June 2018
    Easy location, very lovely people who are kind and cordial. Perfect place to stay for a quick Eastern Shore visit.
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    About this property
    Spacious room w old pine floors, comes with semi-private bathroom, breakfast and some meals provided, in a charming Victorian in delightful town, half acre lot and shared use of rooms. Out and out close for 15 scenic launching areas for boating. Less than 5 mins to spectacular sunsets at Betterton....
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    Location Information
    Still Pond, Maryland 21667
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Centreville
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Patio
    • Air Conditioning
    • Private Garden
    • Washer
    • Wi-Fi
    • Secure Parking
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stunning upscale private apartment that sleeps 3. Located in a private setting at Wye Branch Manor. Less than 10 miles to golf, outlet shopping, hiking trails and the Wye River. 15 miles to historic Easton, 20 minutes to Saint Michael's and Oxford. The apartment is 1 mile from Wye Mills, there is a...
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    Location Information
    Centreville, Maryland 21671
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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