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Search results; 302 homes in Chestertown

Home in Chestertown
Shabby-chic with a fireplace and backyard
2 bedrooms, 2 beds, 2 private baths
Aug 21 – 26
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4.93 out of 5 average rating, 27 reviews
Top guest favorite
Apartment in Chestertown
A secluded carriage house with garden views
4.97 out of 5 average rating, 291 reviews, 2 beds, 1 bath
Aug 29 – Sep 3
Top guest favorite
Home in Chestertown
2 minutes from High Street Wharf
4.97 out of 5 average rating, 90 reviews, 2 bedrooms, 3 beds, 2 baths
Sep 6 – 11
Top guest favorite
Home in Chestertown
Renovated with a hot tub and fire pit
4.98 out of 5 average rating, 186 reviews, 3 bedrooms, 3 beds, 2 baths
Aug 15 – 20
Top guest favorite
Home in Chestertown
Historic estate on a town-center acre
5.0 out of 5 average rating, 247 reviews, 5 bedrooms, 6 beds, 4 baths
Aug 30 – Sep 4
Top guest favorite
Home in Chestertown
3-minute walk to historic downtown
4.96 out of 5 average rating, 74 reviews, 2 bedrooms, 3 beds, 1.5 baths
Aug 20 – 25
Superhost
Guesthouse in Chestertown
Carriage house with garden, near downtown
4.86 out of 5 average rating, 196 reviews, 1 bed, 1 bath
Aug 16 – 21
Top guest favorite
Guest suite in Chestertown
Waterfront suite with dock and creek views
4.99 out of 5 average rating, 252 reviews, 1 bedroom, 2 beds, 1 bath
Aug 17 – 22
Top guest favorite
Home in Chestertown
Waterfront with a hot tub and dock
4.96 out of 5 average rating, 115 reviews, 3 bedrooms, 6 beds, 2 baths
Aug 30 – Sep 4
Top guest favorite
Guesthouse in Chestertown
Renovated carriage house with private gardens
4.99 out of 5 average rating, 69 reviews, 1 bedroom, 2 beds, 1 bath
Aug 13 – 18
Top guest favorite
Guest suite in Chestertown
1870 home with a fire pit downtown
4.99 out of 5 average rating, 141 reviews, 2 bedrooms, 3 beds, 1 bath
Aug 25 – 30
Top guest favorite
Home in Chestertown
Brick patio with string lights near downtown
4.98 out of 5 average rating, 124 reviews, 2 bedrooms, 2 beds, 2.5 baths
Aug 20 – 25
Top guest favorite
Apartment in Chestertown
Rooftop deck with Chester River views
5.0 out of 5 average rating, 151 reviews, 1 bedroom, 1 bed, 1 bath
Aug 27 – Sep 1
Top guest favorite
Apartment in Chestertown
Restored 1877 building, 2 blocks from river
4.98 out of 5 average rating, 142 reviews, 2 bedrooms, 2 beds, 1 bath
Aug 23 – 28
Guest favorite
Home in Chestertown
Restored colonial townhouse near Chester River
5.0 out of 5 average rating, 16 reviews, 2 bedrooms, 2 beds, 1.5 baths
Aug 12 – 17
Home in Chestertown
Waterfront retreat with a fire pit
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 6 beds, 2 baths
Aug 18 – 23
Top guest favorite
Home in Chestertown
1750s colonial 2 blocks from the river
5.0 out of 5 average rating, 60 reviews, 3 bedrooms, 4 beds, 3.5 baths
Aug 16 – 21
Top guest favorite
Home in Chestertown
Renovated 1920s Four Square near waterfront
5.0 out of 5 average rating, 99 reviews, 3 bedrooms, 4 beds, 2.5 baths
Sep 13 – 18
Home in Chestertown
Chestertown home with boat parking
New place to stay, 3 bedrooms, 4 beds, 2 baths
Aug 14 – 19