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Holiday Rentals and Homes in Chestertown, MD

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    1 / 10
    5 of 5 stars (6) Excellent
    Chestertown
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    1 / 28
    5 of 5 stars (2) Excellent
    Chestertown
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Chestertown
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 11
    4 of 5 stars (2) Very good
    Chestertown
    3 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    • x
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    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 stars Reviewed 15 August 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 stars Reviewed 29 August 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 / 22
    4.5 of 5 stars (3) Very good
    Chestertown
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • 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 stars Reviewed 18 October 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 / 21
    5 of 5 stars (1) Excellent
    Chestertown
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Outdoor Dining Area
    • Air Conditioning
    • Parking
    • Grill
    • Washer
    • Wi-Fi
    • Private Garden
    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 stars 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 to...
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    1 / 16
    5 of 5 stars (1) Excellent
    Chestertown
    4 Bedrooms, 9 Bathrooms, Sleeps 8 | Quick View
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    • 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 stars 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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    The following rentals are within 30 kilometers of Chestertown, Maryland.

    1 / 14
    3.5 of 5 stars (16) Average
    Edgemere
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Hot Tub
    • Grill
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    Lake Access with beautiful BEACH. DOCK SLIP available for a nominal fee less than a five minute drive away (make your rez for slip in advance of your arrival!). Sportsman's Feel with several furs decorating the house and abundant wildlife in yard. Main level offers large screen TV in living room -... View all property information
    Location Information
    Edgemere, Maryland 21561
    Stevensville
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Come to our beautiful vacation home and enjoy the scenic view while having fun on the water. Love Point Bay Vacation Home is at the mouth of the Chester River, where it connects to the Chesapeake Bay on Maryland's Eastern Shore. You will feel right at home, yet free of your everyday stress. Leave... View all property information
    Location Information
    Stevensville, Kent Island 21666
    1 / 11
    4.5 of 5 stars (11) Very good
    Edgemere
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    Amenities & Details
    • Outdoor Dining Area
    • Wi-Fi
    • Grill
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    The most central location for activities in the Deep Creek and Laurel Highlands area. Less than 20 minutes to Casino fun at Nemacolin, PA. Over 60 private acres to explore and enjoy. SNOW MOBILES and FOUR-WHEELERS welcome The best area fishing is within 10 minutes: Bear Creek, Yough river, and the... View all property information
    Location Information
    Edgemere, Maryland 21531
    5 of 5 stars Reviewed 10 August 2014
    We got to the cabin on a sat. And it was ready. We were really excited to get away from everything amd when you go there its peace and quite. The kids loved being able to play...
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    1 / 12
    5 of 5 stars (1) Excellent
    Grasonville
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Amenities & Details
    • Internet Access
    • Hot Tub
    • Satellite TV
    • Waterfront
    • Patio
    • Air Conditioning
    • DVD Player
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Welcome to Baydreams vacation home, a unique waterfront vacation home situated near the Kent Narrows in Queen Anne's County, on the Eastern Shore of Maryland. Book the comfort and convenience of a 4 bedroom 3 bath home offering a unique lodging to the discriminating traveler that other... View all property information
    Location Information
    Grasonville, Maryland 21638
    5 of 5 stars Reviewed 12 August 2015
    Baydreams backs onto a Chesapeake Bay inlet. The view from the back windows is beautiful and tranquil. We were particularly impressed with a close view of ospreys nesting behind a...
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    1 / 21
    5 of 5 stars (3) Excellent
    Chester
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • DVD Player
    • Patio
    • Satellite TV
    • Waterfront
    • Wi-Fi
    • Washer
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Chester, Kent Island 21619
    5 of 5 stars Reviewed 6 January 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...
    5 of 5 stars Reviewed 29 July 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. The...
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    1 / 15
    4 of 5 stars (2) Very good
    Rock Hall
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
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    • x
    About this property
    The Cottage takes advantage of its unique environment with a large deck overlooking the extensive lawn and the tranquil waters of Spring Cove. The deck includes a dining set and barbeque grill.The first level includes a screened porch accessed through a first floor bedroom The Cottage is oriented... View all property information
    Location Information
    Rock Hall, Maryland 21661
    4 of 5 stars Reviewed 16 September 2014
    My sisters and mother stayed three nights in this quaint house with great views of one of the marina's and cove area. The downstairs was perfect my mother, with a screened in...
    4 of 5 stars Reviewed 19 August 2014
    My family was looking for a relaxing getaway that would be an alternative to another week at the beach. We found the perfect spot at this cottage near Rock Hall. We rented with no...
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    Rock Hall
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Enjoy the gentle tidal waters of the Chesapeake Bay and its tributaries from your private overlook. The Captain’s Quarters at Spring Cove is a crisp and contemporary second floor living space with great water views. An exterior stairway leads to an ample deck where you can enjoy breakfast and... View all property information
    Location Information
    Rock Hall, Maryland 21661
    1 / 35
    5 of 5 stars (1) Excellent
    Chester
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    Amenities & Details
    • Satellite TV
    • Hot Tub
    • Parking
    • Washer
    • Internet Access
    • Waterfront
    • Balcony
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Swan Cove Condominiums at Kent Narrows(#49064) with private beach and views of the Chesapeake bay! - Brand new luxury condominium with 3000 sq ft, 4 bedrooms, 3 ½ bathrooms, one large family room with open kitchen, one large sunny living room and dinning area. There are 2 king size bed, 2 queen... View all property information
    Location Information
    Chester, Kent Island 21619
    5 of 5 stars Reviewed 11 January 2016
    My family used this home for 10 days over Christmas and New Year. It was just perfect. Plenty of room for our Christmas tree, decorations and packages. Spotlessly clean bedrooms...
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    1 / 17
    5 of 5 stars (3) Excellent
    Rock Hall
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Air Conditioning
    • Shared Outdoor Pool...
    • Washer
    • Satellite TV
    • Patio
    • DVD Player
    • Porch
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This Spacious Home provides 3 Bedrooms and 2 bathrooms. Each room sleeps 2 people comfortably, and an old fashion cot is provided to sleep one more. This home is completely equipped with all the comforts of home. The Central location is in the heart of the Marina district, steps from Waterman’s... View all property information
    Location Information
    Rock Hall, Maryland 21661
    1 / 26
    5 of 5 stars (1) Excellent
    Stevensville
    3 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • Washer
    • Private Outdoor...
    • Satellite TV
    • Hot Tub
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Have the ultimate Maryland getaway by staying at this remarkable Stevensville vacation rental home, surrounded by approximately 20 breathtaking acres of open space with picturesque Eastern Shore views. Whether you're in the mood for a relaxing escape in the great outdoors or a vacation filled with... View all property information
    Location Information
    Stevensville, Kent Island 21666
    5 of 5 stars Reviewed 10 May 2016
    From the moment you ride up the driveway you already know you are in for a wonderful experience. From the cathedral ceilings to the beautiful decor this home welcomes you. The...
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    Galena
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    A very relaxed area to go swimming, tubing, fishing and boating. You have to get in a car to go to a store about 2 miles for food , etc. We have nice restaurants near by and also golf about 5 miles down the road. View all property information
    Location Information
    Galena, Maryland 21625
    Rock Hall
    3 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Washer
    • Grill
    • Parking
    • Porch
    • Patio
    Suitability
    • Pet-friendly
    • Child-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... View all property information
    Location Information
    Rock Hall, Maryland 21661
    Middle River
    4 Bedrooms, 3 Bathrooms, Sleeps 16 | Quick View
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    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    About this property
    The boat is close to the BWI Airport, Baltimore, laundry services, a drive-in movie theater, and great local restaurants. And it FLOATS! It's a sail boat! There are plenty of beds, and it's at the end of a nice, quiet dock (but that doesn't mean you have to be quiet). The Bahama Star is good for... View all property information
    Location Information
    Middle River, Maryland 21220
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    1 / 23
    2 of 5 stars (1) Poor
    Stevensville
    4 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    Amenities & Details
    • Grill
    • Washer
    • Patio
    • Air Conditioning
    • Satellite TV
    • Internet Access
    • Waterfront
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Beautiful 4 Bedroom, 4 Bath Quiet Waterfront Property, 3 queen bedrooms, 1 twin beds, 4 baths, two stories, fantastic master bedroom with mater bath complete with Roman soaking tub. Deck off of the master bedroom. Formal living room, Family room, Glass Sunroom, eat in kitchen, this spacious comes... View all property information
    Location Information
    Stevensville, Kent Island 21666