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Search results; 587 homes in Chestertown

Top guest favourite
Guest suite in Chestertown
Chestertown - Eastern Shore Getaway
1 bedroom, 2 beds, 1 private bathroom
10–15 Aug
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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
20–25 Jul
4.97 out of 5 average rating, 279 reviews
Top guest favourite
Serviced apartment in Chestertown
Waterfront historic district 1BR Apartment
1 bedroom, 1 king bed, 1 bathroom
18–23 Jul
5.0 out of 5 average rating, 145 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, 240 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, 132 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, 249 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, 85 reviews
Top guest favourite
Home in Chestertown
High Tide & Hound
2 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
4.98 out of 5 average rating, 80 reviews
Top guest favourite
Home in Chestertown
Harbor View Haven | Waterfront w/ Hot Tub + Dock!
3 bedrooms, 6 beds, 2 bathrooms
10–15 Jul
4.95 out of 5 average rating, 107 reviews
Superhost
Guest house in Chestertown
Cozy Carriage House
1 queen bed, 1 bathroom
5–10 Jul
4.86 out of 5 average rating, 192 reviews
Top guest favourite
Home in Chestertown
Charming Haven on High
2 bedrooms, 3 beds, 1.5 bathrooms
5–10 Jul
4.95 out of 5 average rating, 65 reviews
Guest favourite
Flat in Chestertown
1-br apt in downtown Chestertown (Unit 1)
1 bedroom, 1 queen bed, 1 bathroom
1–6 Jul
4.9 out of 5 average rating, 93 reviews
Top guest favourite
Guest house in Chestertown
Owl Cottage - Cozy, Private & Walkable to Town
1 bedroom, 2 beds, 1 bathroom
7–12 Jul
4.98 out of 5 average rating, 62 reviews
Home in Chestertown
Riverside at Pear Tree Point | Waterfront Escape
3 bedrooms, 6 beds, 2 bathrooms
5–10 Jul
Guest favourite
Home in Chestertown
Relaxing Waterfront - Golf Course & Sunset Views
3 bedrooms, 6 beds, 3 bathrooms
6–11 Jul
4.91 out of 5 average rating, 34 reviews
Guest favourite
Home in Chestertown
Riverfront Retreat
6 bedrooms, 11 beds, 5.5 bathrooms
12–17 Jul
5.0 out of 5 average rating, 5 reviews
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, 180 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, 179 reviews
Guest favourite
Room in Still Pond
Room 2 Civil War Era House
1 queen bed, 1 bathroom
1–6 Jul
4.87 out of 5 average rating, 60 reviews