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Vacation Rentals in Chestertown, MD and nearby

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All 16 Rentals in the Chestertown Area
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From
$259
Per Night
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1 / 9
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Chestertown
1 Bedroom, 1 Bathroom, Sleeps 2
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From
$145
Per Night
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1 / 11
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Chestertown
3 Bedrooms, 1 Bathroom, Sleeps 7
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From
$95
Per Night
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1 / 10
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Chestertown
1 Bedroom, 1 Bathroom, Sleeps 4
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From
$110
Per Night
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1 / 28
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Chestertown
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (2) Make Inquiry
Amenities & Details
  • Patio
  • Internet Access
  • Grill
  • Porch
  • Refrigerator
  • TV
  • Air Conditioning
  • Water Views
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This cozy one-bedroom house is a wonderful spot for a weekend getaway or as a base to discover the culture, history and cuisine of Maryland's Eastern Shore. Enjoy nature, birds - bald eagles, ospreys, blue herons - stunning sunsets and more by the bay. The one-bedroom house includes full kitchen,... View all property information
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5 of 5 stars Reviewed June 10, 2014
My husband and I were lucky enough to stay in a charming little guest house on the Bay (Tolchester area of Chestertown, MD). House is almost right on the water, very clean, very...
5 of 5 stars Reviewed June 9, 2014
I stayed at Francesca's lovely Bayview cottage on the Chesapeake Bay in Tolchester, Maryland this weekend. The cottage is delightful, with porches on three sides, comfy beds, and...
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From
$295
Per Night
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1 / 12
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Chestertown
3 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
Details Reviews (3) Make Inquiry
Amenities & Details
  • Ceiling Fans
  • Refrigerator
  • Dishwasher
  • Microwave
  • Washer
  • Dryer
  • DVD Player
  • Deck
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • 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
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3 of 5 stars Reviewed October 18, 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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The following rentals are within 20 miles of Chestertown, Maryland.

From
$250
Per Night
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1 / 17
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Rock Hall
3 Bedrooms, 2 Bathrooms, Sleeps 7
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Amenities & Details
  • Dryer
  • Grill
  • TV
  • DVD Player
  • Microwave
  • VCR
  • Refrigerator
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • 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
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From
$115
Per Night
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1 / 5
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Galena
2 Bedrooms, 1 Bathroom, Sleeps 5
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Amenities & Details
  • # Of Bathrooms
  • Guest Count
  • Number Of Bedrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • ?
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
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From
$250
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1 / 15
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Rock Hall
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Guest Count
  • Number Of Bedrooms
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • 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
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4 of 5 stars Reviewed September 16, 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 August 19, 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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From
$180
Per Night
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1 / 12
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Rock Hall
1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Guest Count
  • Number Of Bedrooms
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • 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
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From
$209
Per Night
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1 / 11
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Stevensville
2 Bedrooms, 1 Bathroom, Sleeps 6
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Amenities & Details
  • Number Of Bedrooms
  • # Of Bathrooms
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • 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
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From
$180
Per Night
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1 / 21
Chester
4 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Microwave
  • TV
  • Fireplace
  • Washer
  • DVD Player
  • Patio
  • Dishwasher
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • 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
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5 of 5 stars 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. The...
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From
$300
Per Night
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1 / 30
Centreville
4 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Microwave
  • Fireplace
  • Grill
  • Dishwasher
  • Stove
  • Parking
  • Patio
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This house is on the former estate of John Raskob, builder of the Empire State Building. The four-bedroom, two-bath house is one of seven that Raskob built for his farm employees. Now it has its own dock and swimming pool fronting on Grove Creek, with access to the Chester River and Chesapeake... View all property information
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From
$375
Per Night
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1 / 37
Chester
4 Bedrooms, 4 Bathrooms, Sleeps 10
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Amenities & Details
  • TV
  • Refrigerator
  • Washer
  • Parking
  • Hot Tub
  • Dryer
  • Stove
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • 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
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From
$575
Per Night
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1 / 23
Stevensville
4 Bedrooms, 4 Bathrooms, Sleeps 14
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Amenities & Details
  • Microwave
  • Garage
  • Dishwasher
  • DVD Player
  • Stove
  • Parking
  • Washer
  • Fireplace
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • 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
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From
$450
Per Night
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1 / 12
Grasonville
4 Bedrooms, 3 Bathrooms, Sleeps 10
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Amenities & Details
  • Refrigerator
  • Parking
  • DVD Player
  • Garage
  • Microwave
  • Hot Tub
  • Fireplace
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • 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
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From
$235
Per Night
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1 / 6
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Rock Hall
3 Bedrooms, 1 Bathroom, Sleeps 8
Details Make Inquiry
Amenities & Details
  • Ceiling Fans
  • Grill
  • Microwave
  • Patio
  • Washer
  • Porch
  • Air Conditioning
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
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
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Suitability

  • Wheelchair access (0)
  • Elder access (7)
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  • Pet friendly (4)
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