Search results; 351 homes in Chestertown

Top guest favourite
Guest suite in Chestertown
Chestertown - Eastern Shore Getaway
1 bedroom, 2 beds, 1 private bathroom
22–27 Jul
,
4.98 out of 5 average rating, 197 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
Superhost
Home in Chestertown
114 High - Lux Home Downtown Chestertown Sleeps 11
5 bedrooms, 7 beds, 3.5 bathrooms
20–25 Nov
5.0 out of 5 average rating, 12 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, 281 reviews
Top guest favourite
Home in Chestertown
Lovely Home in Chestertown With Free EV Charging
3 bedrooms, 4 beds, 2.5 bathrooms
5–10 Jul
5.0 out of 5 average rating, 95 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
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
Superhost
Home in Chestertown
Primrose Cottage~Walk to Downtown Chestertown
3 bedrooms, 4 beds, 1 bathroom
5–10 Jul
5.0 out of 5 average rating, 4 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, 108 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
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
Relaxing Waterfront - Golf Course & Sunset Views
3 bedrooms, 6 beds, 3 bathrooms
6–11 Jul
4.91 out of 5 average rating, 35 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
Guest favourite
Loft in Chestertown
Loft at Fountain Park - Prime Downtown Location
4 bedrooms, 5 beds, 2.5 bathrooms
5–10 Jul
4.93 out of 5 average rating, 85 reviews
Home in Chestertown
Riverside at Pear Tree Point | Waterfront Escape
3 bedrooms, 6 beds, 2 bathrooms
5–10 Jul
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, 81 reviews
Top guest favourite
Home in Betterton
Ruby's Sea Glass Cottage near Betterton Beach
3 bedrooms, 5 beds, 1 bathroom
5–10 Jul
4.98 out of 5 average rating, 64 reviews
Top guest favourite
Home in Worton
Cozy Cape Cod in worton MD
3 bedrooms, 4 beds, 3 bathrooms
5–10 Jul
5.0 out of 5 average rating, 16 reviews
Guest favourite
Home in Chestertown
Waterfront Paradise w/ Pier - kayak to Chestertown
3 bedrooms, 7 beds, 2 bathrooms
25–30 Oct
4.91 out of 5 average rating, 65 reviews