Search results; 399 homes in Chestertown

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Guest favourite
Home in Chestertown
NEW Chestertown Retreat
6 guests3 bedrooms4 beds1.5 bathrooms
8–13 Aug
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8–13 Aug
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₹97,148 for 5 nights

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Top guest favourite
Flat in Chestertown
Waterfront historic district 1BR Apartment
1 king bed
1–6 Aug
₹87,703 for 5 nights
5.0 out of 5 average rating, 117 reviews
Top guest favourite
Guest suite in Chestertown
Chestertown - Eastern Shore Getaway
2 beds
26–31 Aug
₹65,652 for 5 nights
4.98 out of 5 average rating, 167 reviews
Guest favourite
Guest house in Chestertown
Cozy Carriage House
1 queen bed
1–6 Aug
₹66,457 for 5 nights
4.89 out of 5 average rating, 177 reviews
Top guest favourite
Flat in Chestertown
Bright, new apartment in the heart of Chestertown
2 beds
1–6 Aug
₹1,15,997 for 5 nights
4.98 out of 5 average rating, 99 reviews
Top guest favourite
Casa particular in Chestertown
Red, White & Waterview Studio Apt with pool
2 beds
4–9 Aug
₹71,390 for 5 nights
4.92 out of 5 average rating, 154 reviews
Guest favourite
Home in Chestertown
Charming Haven on High
3 beds
1–6 Aug
₹1,07,237 for 5 nights
4.97 out of 5 average rating, 32 reviews
Top guest favourite
Flat in Chestertown
Private cozy cottage - center of Chestertown .
1 king bed
10–15 Aug
₹87,976 for 5 nights
4.96 out of 5 average rating, 241 reviews
Guest favourite
Home in Chestertown
River Cottage, Chestertown
2 queen beds
1–6 Aug
₹1,22,844 for 5 nights
4.94 out of 5 average rating, 32 reviews
Room in Chestertown
Stay with OksanaHosting for 8 years,
Private Bedroom and bath in Chestertown, MD
1–6 Aug
₹43,298 for 5 nights
4.87 out of 5 average rating, 144 reviews
Top guest favourite
Home in Chestertown
Cozy 3-bedroom home w/ Hot tub & firepit
3 queen beds
23–28 Aug
₹1,05,324 for 5 nights
4.97 out of 5 average rating, 135 reviews
Guest favourite
Cottage in Centreville
Captain’s Quarters - Unique home on Corsica River!
2 beds
3–8 Aug
₹93,140 for 5 nights
4.94 out of 5 average rating, 48 reviews
Top guest favourite
Home in Chestertown
The Portside Manor - Queen Street Chestertown
4 beds
3–8 Aug
₹1,99,370 for 5 nights
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Chestertown
Magnolia House: walk to shops, restaurants, river
4 beds
1–6 Aug
₹1,43,989 for 5 nights
5.0 out of 5 average rating, 44 reviews
Guest favourite
Room in Still Pond
Stay with NancyHosting for 6 years,
Room 2 Civil War Era House
1–6 Aug
₹48,836 for 5 nights
4.86 out of 5 average rating, 50 reviews
Top guest favourite
Home in Chestertown
Entire River Front Home - 4 Bedrooms 4.5 Baths
5 beds
2–7 Aug
₹2,76,902 for 5 nights
4.99 out of 5 average rating, 108 reviews
Guest favourite
Home in Chestertown
River front cottage with private dock & water fun
11 beds
9–14 Sept
₹2,42,667 for 5 nights
4.97 out of 5 average rating, 91 reviews
Top guest favourite
Home in Betterton
Grandma’s Cottage
4 beds
4–9 Aug
₹1,00,692 for 5 nights
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Chestertown
Waterfront w/ Hot Tub + Dock | Harbor View Haven
6 beds
25–30 Aug
₹2,15,984 for 5 nights
4.95 out of 5 average rating, 77 reviews