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Search results; 298 homes in Chestertown

Descriptions are based on details hosts provide
Top guest favourite
Guest suite in Chestertown
Chestertown - Eastern Shore Getaway
1 bedroom, 2 beds, 1 private bathroom
18–23 Aug
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4.98 out of 5 average rating, 199 reviews
Top guest favourite
Flat in Chestertown
A secluded carriage house with garden views
2 king beds, 1 bathroom
27 Jul – 1 Aug
4.97 out of 5 average rating, 285 reviews
Top guest favourite
Home in Chestertown
Charming Haven on High
2 bedrooms, 3 beds, 1.5 bathrooms
17–22 Jul
4.96 out of 5 average rating, 68 reviews
Guest favourite
Home in Chestertown
Restored colonial townhouse near Chester River
2 bedrooms, 2 queen beds, 1.5 bathrooms
20–25 Jul
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Chestertown
2 minutes from High Street Wharf
2 bedrooms, 3 beds, 2 bathrooms
2–7 Aug
4.98 out of 5 average rating, 84 reviews
Top guest favourite
Home in Chestertown
The Garden Estate: Historic Town Center Home
5 bedrooms, 6 beds, 4 bathrooms
25–30 Aug
5.0 out of 5 average rating, 243 reviews
Top guest favourite
Home in Chestertown
Lovely Home in Chestertown With Free EV Charging
3 bedrooms, 4 beds, 2.5 bathrooms
9–14 Aug
5.0 out of 5 average rating, 95 reviews
Top guest favourite
Serviced apartment in Chestertown
Waterfront historic district 1BR Apartment
1 bedroom, 1 king bed, 1 bathroom
27 Aug – 1 Sept
5.0 out of 5 average rating, 147 reviews
Top guest favourite
Townhouse in Chestertown
Pole Pole House - Downtown Chestertown Retreat
2 bedrooms, 3 beds, 1 bathroom
28 Jul – 2 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Chestertown
Renovated with a hot tub and fire pit
3 bedrooms, 3 queen beds, 2 bathrooms
15–20 Aug
4.98 out of 5 average rating, 181 reviews
Top guest favourite
Home in Chestertown
Remodeled Victorian with a gourmet kitchen
4 bedrooms, 8 beds, 2.5 bathrooms
15–20 Jul
4.96 out of 5 average rating, 138 reviews
Top guest favourite
Guest house in Chestertown
Renovated 1800s carriage house with gardens
1 bedroom, 2 beds, 1 bathroom
25–30 Jul
4.98 out of 5 average rating, 64 reviews
Guest favourite
Loft in Chestertown
Loft overlooking Fountain Park downtown
4 bedrooms, 5 beds, 2.5 bathrooms
15–20 Jul
4.93 out of 5 average rating, 86 reviews
Top guest favourite
Home in Rock Hall
Historic waterman’s cottage with sunset views
1 bedroom, 1 queen bed, 1 bathroom
19–24 Jul
4.94 out of 5 average rating, 66 reviews
Top guest favourite
Home in Chestertown
Harbor View Haven | Waterfront w/ Hot Tub + Dock!
3 bedrooms, 6 beds, 2 bathrooms
23–28 Aug
4.95 out of 5 average rating, 110 reviews
Top guest favourite
Home in Chestertown
Relaxing Waterfront - Golf Course & Sunset Views
3 bedrooms, 6 beds, 3 bathrooms
15–20 Jul
4.97 out of 5 average rating, 35 reviews
Home in Chestertown
3 Mi to Washington College! Updated Home w/ Patio
3 bedrooms, 4 beds, 1 bathroom
20–25 Jul
4.33 out of 5 average rating, 3 reviews
Top guest favourite
Home in Chestertown
River house with dock and private access
4 bedrooms, 7 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Chestertown
Brick patio with string lights near downtown
2 bedrooms, 2 queen beds, 2.5 bathrooms
26–31 Jul
4.98 out of 5 average rating, 123 reviews