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Cottages, Villas, Apartments in Chestertown
Holiday Rentals
USA
Maryland (MD)
Cottages, Villas, Apartments in Chestertown
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Internet or Wifi (28)
Air Conditioning (28)
Washer/Dryer (26)
Grill (22)
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Suitability
Kid friendly (27)
Pet friendly (10)
Wheelchair access (0)
Elder access (0)
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Holiday Rental House (24)
Condominium/Apartment (4)
Cabin Holiday Rental (0)
Private Room (0)
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Distinctive Features
Waterfront (14)
Private Chef (0)
Private Beach (0)
Ski In/Ski Out (0)
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Distance from
5 mi
Kent County Visitors Center
MassoniArt Gallery
Garfield Center for the Arts at the Prince Theatre
Historical Society of Kent County
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28 rentals
in Chestertown.
Carriage House Hideaway in Middle of Chestertown
43
Condo/Apartment
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0 bedrooms
1 bathroom
Sleeps 2
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First Floor Studio Apartment in Historic Chestertown
44
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 3
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As seen on
Breathtaking waterfront home on the Chester River
19
Holiday Rental House
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4 bedrooms
5 bathrooms
Sleeps 10
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As seen on
Harbor View Haven | Waterfront w/ HOT TUB + Dock!
13
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 10
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As seen on
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
17
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 8
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As seen on
Circa 1900 Home in the Heart of Historic Downtown Chestertown
17
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 6
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As seen on
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
29
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 10
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Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
23
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
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As seen on
Newly restored apartment in the heart of Chestertown
16
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
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Historic Downtown Garden Oasis with Private Patio
24
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Historic Manor House on Beautiful Eastern Shore Estate
10
Holiday Rental House
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6 bedrooms
5 bathrooms
Sleeps 13
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Cottage within walking distance to the Bay!
5
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 4
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As seen on
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
77
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Contemporary waterfront house with private dock & kayaks!
65
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
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Cottage upper Chesapeake Eastern Shore on major creek with shared pool and dock.
3
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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As seen on
River Lodge, Casual Riverfront setting
10
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 10
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As seen on
Victorian Hideaway: Beautiful Exterior, Modern interior
30
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
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As seen on
The Portside Manor - Queen Street Chestertown - Walking Distance to Downtown
1
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 8
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As seen on
The Lazy River House
7
Holiday Rental House
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3 bedrooms
4 bathrooms
Sleeps 10
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As seen on
Langford Creek Estate | Waterfront w/ HOT TUB + Deck!
5
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
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As seen on
Goose Landing on Fairlee Creek
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 10
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As seen on
Historic Stepne Manor on Maryland's Eastern Shore
2
Holiday Rental House
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5 bedrooms
4 bathrooms
Sleeps 15
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As seen on
Country Estate in Historic District
3
Holiday Rental House
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5 bedrooms
4 bathrooms
Sleeps 10
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As seen on
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
10
Holiday Rental House
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6 bedrooms
7 bathrooms
Sleeps 14
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As seen on
Celebrate Memorial Weekend at a Beautiful Estate with Pool!
8
Holiday Rental House
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11 bedrooms
9 bathrooms
Sleeps 30
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As seen on
Pet-Friendly Home on Chester River w/ Dock!
Holiday Rental House
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7 bedrooms
5 bathrooms
Sleeps 14
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As seen on
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
6
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
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As seen on
Eastern Shore Getaway: Walk to Tolchester Marina!
2
Holiday Rental House
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5 bedrooms
3 bathrooms
Sleeps 10
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As seen on
1
Showing results 1-28 of 28
Frequently Asked Questions about Chestertown
Do any holiday rentals in Chestertown have a pool?
Yes, here are some popular holiday rentals in Chestertown that have a pool:
Carriage House Hideaway in Middle of Chestertown
First Floor Studio Apartment in Historic Chestertown
Breathtaking waterfront home on the Chester River
See all holiday rentals with a pool in Chestertown on Tripadvisor
Do any holiday rentals in Chestertown have internet access?
Yes, here are some popular holiday rentals in Chestertown that have internet access:
Carriage House Hideaway in Middle of Chestertown
First Floor Studio Apartment in Historic Chestertown
Breathtaking waterfront home on the Chester River
See all holiday rentals in Chestertown on Tripadvisor
What are the best pet friendly rentals in Chestertown?
The best pet friendly rentals in Chestertown are:
Carriage House Hideaway in Middle of Chestertown
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
See all pet friendly holiday rentals in Chestertown on Tripadvisor
What are some great rentals in Chestertown that are kid friendly?
Some of the most popular kid friendly rentals in Chestertown are:
Carriage House Hideaway in Middle of Chestertown
First Floor Studio Apartment in Historic Chestertown
Breathtaking waterfront home on the Chester River
See all kid friendly holiday rentals in Chestertown on Tripadvisor
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