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Search results; 307 homes in Chestertown

Top guest favourite
Guest suite in Chestertown
Chestertown - Eastern Shore Getaway
1 bedroom, 1 bed, 1 private bathroom
24–29 Aug
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4.98 out of 5 average rating, 200 reviews
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Flat in Chestertown
Carriage House Studio -Secluded "Treehouse" Escape
2 king beds
29 Aug – 3 Sept
4.97 out of 5 average rating, 289 reviews
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Home in Chestertown
Charming Haven on High
2 bedrooms, 3 beds
5–10 Aug
4.96 out of 5 average rating, 71 reviews
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Home in Chestertown
Harbor View Haven | Waterfront w/ Hot Tub + Dock!
3 bedrooms, 6 beds
25–30 Aug
4.96 out of 5 average rating, 112 reviews
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Home in Chestertown
High Tide & Hound
2 bedrooms, 3 beds
6–11 Sept
4.97 out of 5 average rating, 89 reviews
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Home in Chestertown
Cozy 3-bedroom home w/ Hot tub & firepit
3 bedrooms, 3 queen beds
15–20 Aug
4.98 out of 5 average rating, 184 reviews
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Home in Chestertown
The Garden Estate: Historic Town Center Home
5 bedrooms, 6 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 247 reviews
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Guest suite in Chestertown
House On The Hill - Historic Private Second Floor
2 bedrooms, 3 beds
9–14 Aug
4.99 out of 5 average rating, 139 reviews
Guest favourite
Home in Chestertown
Heart of Historic Chestertown - Church Alley
2 bedrooms, 2 queen beds
10–15 Aug
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Serviced apartment in Chestertown
Waterfront historic district 1BR Apartment
1 bedroom, 1 king bed
9–14 Aug
5.0 out of 5 average rating, 150 reviews
Guest favourite
Home in Chestertown
Primrose Cottage~Walk to Downtown Chestertown
3 bedrooms, 4 beds
9–14 Aug
5.0 out of 5 average rating, 7 reviews
Home in Chestertown
Private Chester River Retreat | Fire Pit & Views
3 bedrooms, 6 beds
18–23 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Guest suite in Chestertown
Beautiful Waterfront Chestertown Getaway
1 bedroom, 2 beds
8–13 Dec
4.99 out of 5 average rating, 252 reviews
Superhost
Guest house in Chestertown
Cozy Carriage House
1 queen bed
16–21 Aug
4.86 out of 5 average rating, 196 reviews
Top guest favourite
Home in Chestertown
2 Beds, 2.5 Baths - Perfect Downtown Location
2 bedrooms, 2 queen beds
20–25 Aug
4.98 out of 5 average rating, 124 reviews
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Townhouse in Chestertown
Pole Pole House - Downtown Chestertown Retreat
2 bedrooms, 3 beds
9–14 Aug
5.0 out of 5 average rating, 6 reviews
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Flat in Chestertown
Bright, new apartment in the heart of Chestertown
2 bedrooms, 2 beds
23–28 Aug
4.98 out of 5 average rating, 142 reviews
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Home in Chestertown
Magnolia House is for sale! Historic Chestertown
3 bedrooms, 4 beds
5–10 Aug
5.0 out of 5 average rating, 60 reviews
Top guest favourite
Home in Chestertown
Waterfront Wellness - *With Pool and Hot Tub!*
4 bedrooms, 5 beds
22–27 Aug
4.96 out of 5 average rating, 27 reviews