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Search results; 302 homes in Chestertown

Top guest favourite
Flat in Chestertown
Carriage House Studio -Secluded "Treehouse" Escape
Studio, 2 beds, 1 private bathroom
20–25 Aug
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4.97 out of 5 average rating, 283 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
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
Top guest favourite
Home in Chestertown
Cozy 3-bedroom home w/ Hot tub & firepit
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
High Tide & Hound
2 bedrooms, 3 beds, 2 bathrooms
2–7 Aug
4.98 out of 5 average rating, 83 reviews
Top guest favourite
Guest house in Chestertown
Owl Cottage - Cozy, Private & Walkable to Town
1 bedroom, 2 beds, 1 bathroom
13–18 Jul
4.98 out of 5 average rating, 63 reviews
Top guest favourite
Guest suite in Chestertown
Chestertown - Eastern Shore Getaway
1 bedroom, 2 beds, 1 bathroom
18–23 Aug
4.98 out of 5 average rating, 199 reviews
Top guest favourite
Guest suite in Chestertown
House On The Hill - Historic Private Second Floor
2 bedrooms, 3 beds, 1 bathroom
10–15 Aug
4.99 out of 5 average rating, 134 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
Superhost
Guest house in Chestertown
Cozy Carriage House
1 queen bed, 1 bathroom
10–15 Aug
4.87 out of 5 average rating, 195 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, 241 reviews
Superhost
Townhouse in Chestertown
Pole Pole House - Downtown Chestertown Retreat
2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Chestertown
Heart of Historic Chestertown - Church Alley
2 bedrooms, 2 queen beds, 1.5 bathrooms
12–17 Jul
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Guest suite in Chestertown
Beautiful Waterfront Chestertown Getaway
1 bedroom, 2 beds, 1 bathroom
13–18 Oct
4.99 out of 5 average rating, 251 reviews
Top guest favourite
Casa particular in Chestertown
Red, White & Waterview Studio Apt with pool
1 bedroom, 2 beds, 1 bathroom
31 Jul – 5 Aug
4.92 out of 5 average rating, 183 reviews
Top guest favourite
Home in Chestertown
Classic Victorian in Chestertown
4 bedrooms, 8 beds, 2.5 bathrooms
12–17 Jul
4.96 out of 5 average rating, 138 reviews
Guest favourite
Home in Chestertown
Walk to Historic Chestertown: Dog-Friendly Retreat
2 bedrooms, 3 beds, 2 bathrooms
9–14 Aug
5.0 out of 5 average rating, 15 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, 109 reviews
Guest favourite
Loft in Chestertown
Loft at Fountain Park - Prime Downtown Location
4 bedrooms, 5 beds, 2.5 bathrooms
12–17 Jul
4.93 out of 5 average rating, 85 reviews