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Holiday Homes and Apartments Chestertown, MD and nearby

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All 16 Rentals in the Chestertown Area
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From
$122
Per Night
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1 / 10
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Chestertown
Apartment - 
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (5) Make Enquiry
From
$186
Per Night
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1 / 11
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Chestertown
House Rental - 
3 Bedrooms, 1 Bathroom, Sleeps 7
Bookings
Details Reviews (1) Make Enquiry
From
$379
Per Night
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1 / 12
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Chestertown
House Rental - 
3 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
Details Reviews (3) Make Enquiry
From
$141
Per Night
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1 / 28
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Chestertown
House Rental - 
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • ?
  • ?
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 11 June 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 10 June 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
$333
Per Night
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1 / 9
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Chestertown
Cottage - 
1 Bedroom, 1 Bathroom, Sleeps 2
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Amenities & Details
  • Air Conditioning
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
About this property
Camellia Cottage is a ca. 1950 ranch house apartment located on the property of the award-winning Brampton Bed & Breakfast Inn. The newest accommodation at our Chestertown Bed and Breakfast is a chic, Danish Modern furnished one bedroom flat. With it's own entrance, a fully equipped kitchen and a... View all property information
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The following rentals are within 30 kilometres of Chestertown, Maryland.

From
$321
Per Night
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1 / 17
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Rock Hall
House Rental - 
3 Bedrooms, 2 Bathrooms, Sleeps 7
Details Reviews (3) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • 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
$321
Per Night
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1 / 15
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Rock Hall
Cottage - 
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (2) Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • 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 17 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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From
$231
Per Night
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1 / 21
Chester
House Rental - 
4 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Private Fishing...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • 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 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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From
$386
Per Night
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1 / 30
Centreville
House Rental - 
4 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (3) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Private Outdoor...
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • 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
$269
Per Night
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1 / 11
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Stevensville
Apartment - 
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
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
$148
Per Night
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1 / 5
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Galena
Cottage - 
2 Bedrooms, 1 Bathroom, Sleeps 5
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • 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
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From
$231
Per Night
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1 / 12
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Rock Hall
Apartment - 
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • 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
$579
Per Night
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1 / 12
Grasonville
House Rental - 
4 Bedrooms, 3 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • 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
$482
Per Night
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1 / 37
Chester
House Rental - 
4 Bedrooms, 4 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • 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
$739
Per Night
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1 / 23
Stevensville
House Rental - 
4 Bedrooms, 4 Bathrooms, Sleeps 14
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • 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
$302
Per Night
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1 / 6
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Rock Hall
Bungalow - 
3 Bedrooms, 1 Bathroom, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Grill
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • 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)
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  • Smoking allowed (0)

Amenities

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