Best price vacation rentals in Chestertown, MD 21620, USA • 38 Listings
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Chestertown, MD 21620, USA Vacation Rentals | 

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5.0 (6)
Beautiful Waterfront Estate
Up to 27 guests
Airbnb$2,107
Vrbo$2,463
Average Nightly Rate
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5.0 (32)
Historic Stepne Manor on Maryland's Eastern Shore
Up to 15 guests
Vrbo$775
Airbnb$947
Average Nightly Rate
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5.0 (76)
Country Estate in Historic District
Up to 10 guests
Airbnb$215
Vrbo$260
Average Nightly Rate
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5.0 (8)
Manor House on Beautiful Eastern Shore Estate
Up to 13 guests
Airbnb$990
Vrbo$990
Average Nightly Rate
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5.0 (76)
Carriage House Hideaway in Middle of Chestertown
Up to 2 guests
Airbnb$120
Vrbo$125
Average Nightly Rate
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5.0 (130)
Waterfront w/Deepwater Pier Walking Distance to Downtown Chestertown
Up to 8 guests
Airbnb$396
Vrbo$450
Average Nightly Rate
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5.0 (54)
Chestertown's Pet-Friendly Little Red Cottage
Up to 4 guests
Airbnb$218
Vrbo$225
Average Nightly Rate

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5.0 (22)
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
Up to 8 guests
Vrbo$450
Airbnb$465
Average Nightly Rate
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4.8 (69)
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Up to 6 guests
Airbnb$365
Vrbo$365
Average Nightly Rate

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5.0 (36)
3 BR Patriot House- UNIT ONE /Mid-Century Modern
Up to 6 guests
Airbnb$329
Average Nightly Rate
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5.0 (137)
Rivershore Retreat
Up to 6 guests
Airbnb$295
Average Nightly Rate
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5.0 (131)
Town House in the Heart of Chestertown
Up to 4 guests
Airbnb$200
Average Nightly Rate
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5.0 (47)
RIVER WATCH
Up to 4 guests
Airbnb$275
Average Nightly Rate
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5.0 (63)
The Bittersweet
Up to 4 guests
Airbnb$85
Average Nightly Rate
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5.0 (107)
Cozy Carriage House
Up to 2 guests
Airbnb$98
Average Nightly Rate
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5.0 (90)
Duchess of Kent: Walk to downtown & College
Up to 12 guests
Airbnb$338
Average Nightly Rate
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5.0 (16)
Quiet, Shabby-chic home in downtown Chestertown
Up to 6 guests
Airbnb$268
Average Nightly Rate
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5.0 (20)
Patriot House - Unit Two
Up to 7 guests
Airbnb$332
Average Nightly Rate
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5.0 (140)
Historic Chestertown
Up to 5 guests
Airbnb$311
Average Nightly Rate
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5.0 (44)
Chestertown - Eastern Shore Getaway
Up to 4 guests
Airbnb$99
Average Nightly Rate
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5.0 (33)
River front cottage with private dock & water fun
Up to 10 guests
Airbnb$444
Average Nightly Rate
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5.0 (59)
Piney Grove Farm
Up to 12 guests
Airbnb$600
Average Nightly Rate
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5.0 (26)
The Patriot House-Chestertown, MD
Up to 13 guests
Airbnb$414
Average Nightly Rate
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5.0 (124)
Beautiful Waterfront Chestertown Getaway
Up to 2 guests
Airbnb$108
Average Nightly Rate
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5.0 (9)
1-br apt in downtown Chestertown
Up to 2 guests
Airbnb$164
Average Nightly Rate
  1. United States
  2. Maryland
  3. Chestertown Vacation Rental Price Comparison

Compare Airbnb vs. Booking.com vs. Vrbo prices for vacation rentals in Chestertown, MD 21620, USA

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