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Search results; 301 homes in Chestertown

Top guest favourite
Flat in Chestertown
Carriage House Studio -Secluded "Treehouse" Escape
Studio, 2 beds, 1 private bathroom
12–17 Jul
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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
1–6 Aug
5.0 out of 5 average rating, 147 reviews
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Guest house in Chestertown
Owl Cottage - Cozy, Private & Walkable to Town
1 bedroom, 2 beds, 1 bathroom
12–17 Jul
4.98 out of 5 average rating, 63 reviews
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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
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, 133 reviews
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Guest suite in Chestertown
Chestertown - Eastern Shore Getaway
1 bedroom, 2 beds, 1 bathroom
10–15 Aug
4.98 out of 5 average rating, 198 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
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
Top guest favourite
Home in Chestertown
Waterfront Home with Private Dock | Peaceful Stay
2 bedrooms, 2 beds, 1.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 87 reviews
Superhost
Guest house in Chestertown
Cozy Carriage House
1 queen bed, 1 bathroom
2–7 Aug
4.87 out of 5 average rating, 194 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
Home in Chestertown
Lovely Home in Chestertown With Free EV Charging
3 bedrooms, 4 beds, 2.5 bathrooms
9–14 Jul
5.0 out of 5 average rating, 95 reviews
Top guest favourite
Casa particular in Chestertown
Red, White & Waterview Studio Apt with pool
1 bedroom, 2 beds, 1 bathroom
26–31 Jul
4.92 out of 5 average rating, 182 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, 250 reviews
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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
Top guest favourite
Home in Chestertown
Classic Victorian in Chestertown
4 bedrooms, 8 beds, 2.5 bathrooms
10–15 Jul
4.96 out of 5 average rating, 137 reviews
Guest favourite
Home in Chestertown
Heart of Historic Chestertown - Church Alley
2 bedrooms, 2 queen beds, 1.5 bathrooms
8–13 Jul
5.0 out of 5 average rating, 12 reviews
Guest favourite
Home in Chestertown
River front cottage with private dock & water fun
5 bedrooms, 11 beds, 3 bathrooms
20–25 May
4.96 out of 5 average rating, 105 reviews
Top guest favourite
Home in Chestertown
Relaxing Waterfront - Golf Course & Sunset Views
3 bedrooms, 6 beds, 3 bathrooms
8–13 Jul
4.97 out of 5 average rating, 34 reviews