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Search results; 305 homes in Chestertown

Top guest favourite
Guest suite in Chestertown
Chestertown - Eastern Shore Getaway
1 bedroom, 2 beds, 1 private bathroom
22–27 Jul
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4.98 out of 5 average rating, 197 reviews
Top guest favourite
Flat in Chestertown
Secluded and romantic getaway in Chestertown
2 king beds, 1 bathroom
5–10 Jul
4.97 out of 5 average rating, 282 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, 146 reviews
Top guest favourite
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
Top guest favourite
Home in Chestertown
Gorgeous home in town center & 4 blocks from WAC
5 bedrooms, 6 beds, 4 bathrooms
5–10 Jul
5.0 out of 5 average rating, 241 reviews
Top guest favourite
Guest suite in Chestertown
House On The Hill - Historic Private Second Floor
2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
4.99 out of 5 average rating, 133 reviews
Top guest favourite
Home in Chestertown
Charming Haven on High
2 bedrooms, 3 beds, 1.5 bathrooms
5–10 Jul
4.96 out of 5 average rating, 67 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, 82 reviews
Superhost
Guest house in Chestertown
Cozy Carriage House
1 queen bed, 1 bathroom
5–10 Jul
4.87 out of 5 average rating, 193 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, 86 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
Top guest favourite
Home in Chestertown
Cozy 3-bedroom home w/ Hot tub & firepit
3 bedrooms, 3 queen beds, 2 bathrooms
11–16 Aug
4.98 out of 5 average rating, 180 reviews
Top guest favourite
Casa particular in Chestertown
Red, White & Waterview Studio Apt with pool
1 bedroom, 2 beds, 1 bathroom
6–11 Jul
4.92 out of 5 average rating, 182 reviews
Guest favourite
Home in Chestertown
Heart of Historic Chestertown - Church Alley
2 bedrooms, 2 queen beds, 1.5 bathrooms
6–11 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
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, 14 reviews
Guest favourite
Home in Chestertown
Relaxing Waterfront - Golf Course & Sunset Views
3 bedrooms, 6 beds, 3 bathrooms
6–11 Jul
4.97 out of 5 average rating, 34 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
Superhost
Townhouse in Chestertown
Pole Pole House - Downtown Chestertown Retreat
2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
5.0 out of 5 average rating, 4 reviews