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Chestertown Vacation Rentals

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    All 15 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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    Cottage On Kent1 / 7
    (3)Excellent
    Chestertown
    1 Bedroom, 1 Bathroom, Sleeps 3 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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    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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    • Parking
    • Air Conditioning
    • Private Garden
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 13, 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 January 16, 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
    Retreat at a quiet, water front cottage1 / 14
    (3)Very good
    Chestertown
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Air Conditioning
    • Grill
    • DVD Player
    • Washer
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    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...
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    Location Information
    Chestertown, Maryland 21620
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    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 February 13, 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 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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    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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    Location Information
    Chestertown, Maryland 21620
    Holiday Rental House - 4 Bedrooms, 9 Bathrooms, Sleeps 8
    The following rentals are within 30 kilometres of Chestertown.
    Rock Hall
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Parking
    • Air Conditioning
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    • 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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    Rock Hall, Maryland 21661
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Sailors Crossing1 / 12
    (3)Excellent
    Rock Hall
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Central Heating
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 7, 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 August 15, 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
    Peaceful, Waterfront Home on 3 Acres (pier + western view w/gorgeous sunsets)1 / 21
    (3)Excellent
    Chester
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Patio
    • Cable/satellite TV
    • Waterfront
    • Wi-Fi
    • Washer
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 6, 2016
    We have stayed in this home several times and will return in July. It is a wonderful house with a private master suite at one end, two bedrooms with a 2nd bath at the other.The...
    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...
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    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...
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    Location Information
    Chester, Kent Island 21619
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Centreville
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • 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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    Beautiful Kent Island 4BR, Perfect Location, Close to Chesapeake Bay Beach Club!1 / 12
    (1)Excellent
    Chester
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 24, 2019
    This home is sparkling clean home and flawless. Ten of us stayed there for a wedding and it was even better than we hoped for. Enough room indoors AND outdoors for us to hang...
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    About this property
    Enjoy all that Kent island has to offer--golfing, fishing, crabbing and the laid back island life!! Beautifully remodeled 4 Bedroom house in a great community close to Rt 50 and mins from the Bay Bridge!! Whether you are on Maryland's picturesque Eastern shore for its beaches & water activities...
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    Location Information
    Chester, Kent Island 21619
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    Wye Mills
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Waterfront
    • Washer
    • Private Garden
    • Secure Parking
    • Air Conditioning
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This unique apartment sleeps 5 and is part of the elegant house sitting on 17 private acres in historic Wye Mills with access to a lake. This place is perfect for kayaking, fishing and an overall countryside experience abundant with wildlife. Wye Mills is home to the historic Old Wye Grist Mill...
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    Location Information
    Wye Mills, Talbot County 21679
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 5
    Rock Hall
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious house provides 3 Bedrooms and 1.5 bathrooms. Each bedroom has been freshened in 2019 with new bedding, rugs and paint. The new queen bed mattresses sleep two comfortably, and the cozy living room offers all the comforts of home, WI-FI and cable TV. The house is located in the heart of...
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    Location Information
    Rock Hall, Maryland 21661
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Rock Hall
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Edgemere
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    41' 2016 Brookstone Fifth Wheel RV located at Meehan's Marina on Jones Creek in Sparrows Point, MD. Access to piers, fishing, kayaking and crabbing. Minutes from BWI, Downtown Baltimore and within driving distance to historic Annapolis, MD. This is the RV that we travel with, but we share it when...
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    Location Information
    Edgemere, Maryland 21219
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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