Search results; 351 homes in Chestertown

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Guest favourite
Home in Chestertown
Goose Haven, new waterfront house on Fairlee Creek
12 guests4 bedrooms10 beds3 bathrooms
10–15 Aug
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10–15 Aug
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₹2,20,493 for 5 nights

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Top guest favourite
Flat in Chestertown
Waterfront historic district 1BR Apartment
1 king bed
1–6 Aug
₹87,694 for 5 nights
5.0 out of 5 average rating, 116 reviews
Top guest favourite
Home in Chestertown
High Tide & Hound
Free cancellation
10–15 Aug
₹84,673 for 5 nights
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Guest suite in Chestertown
Chestertown - Eastern Shore Getaway
Free cancellation
26–31 Aug
₹65,645 for 5 nights
4.98 out of 5 average rating, 166 reviews
Top guest favourite
Guest suite in Chestertown
House On The Hill - Historic Private Second Floor
Free cancellation
1–6 Sept
₹58,114 for 5 nights
4.99 out of 5 average rating, 100 reviews
Top guest favourite
Flat in Chestertown
Private cozy cottage - center of Chestertown .
Free cancellation
10–15 Aug
₹87,967 for 5 nights
4.96 out of 5 average rating, 241 reviews
Top guest favourite
Guest suite in Chestertown
Beautiful Waterfront Chestertown Getaway
Free cancellation
30 Sept – 5 Oct
₹74,807 for 5 nights
4.99 out of 5 average rating, 228 reviews
Top guest favourite
Flat in Chestertown
Bright, new apartment in the heart of Chestertown
2 beds
1–6 Aug
₹1,15,986 for 5 nights
4.98 out of 5 average rating, 98 reviews
Guest favourite
Home in Chestertown
Charming Haven on High
Free cancellation
3–8 Aug
₹93,131 for 5 nights
4.97 out of 5 average rating, 31 reviews
Top guest favourite
Home in Chestertown
Cozy 3-bedroom home w/ Hot tub & firepit
Free cancellation
23–28 Aug
₹1,05,313 for 5 nights
4.97 out of 5 average rating, 135 reviews
Guest favourite
Guest house in Chestertown
Cozy Carriage House
Free cancellation
1–6 Aug
₹66,450 for 5 nights
4.89 out of 5 average rating, 177 reviews
Top guest favourite
Casa particular in Chestertown
Red, White & Waterview Studio Apt with pool
2 beds
4–9 Aug
₹70,779 for 5 nights
4.92 out of 5 average rating, 154 reviews
Guest favourite
Home in Chestertown
Holiday Escape to the Riverside
Free cancellation
24–29 Aug
₹2,14,452 for 5 nights
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Farm stay in Chestertown
Blue Heron Farm Waterfront Chalet
Free cancellation
17–22 Aug
₹1,63,608 for 5 nights
4.94 out of 5 average rating, 162 reviews
Top guest favourite
Guest house in Chestertown
Owl Cottage - Cozy, Private & Walkable to Town
Free cancellation
21–26 Sept
₹1,00,178 for 5 nights
5.0 out of 5 average rating, 34 reviews
Room in Chestertown
Stay with OksanaHosting for 8 years,
Private Bedroom and bath in Chestertown, MD
1–6 Aug
₹43,293 for 5 nights
4.87 out of 5 average rating, 144 reviews
Guest favourite
Home in Chestertown
NEW Chestertown Retreat
4 beds
8–13 Aug
₹97,138 for 5 nights
4.98 out of 5 average rating, 47 reviews
Guest favourite
Cottage in Centreville
Captain’s Quarters - Unique home on Corsica River!
Free cancellation
3–8 Aug
₹93,131 for 5 nights
4.93 out of 5 average rating, 46 reviews
Guest favourite
Home in Chestertown
River front cottage with private dock & water fun
Free cancellation
9–14 Sept
₹2,42,643 for 5 nights
4.97 out of 5 average rating, 90 reviews