Search results; 356 homes in Chestertown

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Guest favorite
Casa particular in Chestertown
Red, White & Waterview Studio Apt with pool
3 guests1 bedroom2 beds1 bath
Aug 17 – 22
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Aug 17 – 22
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ﺩ.ﺇ2,691 for 5 nights

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Top guest favorite
Apartment in Chestertown
Private cozy cottage - center of Chestertown .
1 king bed
Aug 18 – 23
ﺩ.ﺇ3,570 for 5 nights
4.96 out of 5 average rating, 242 reviews
Top guest favorite
Apartment in Chestertown
Bright, new apartment in the heart of Chestertown
2 beds
Aug 13 – 18
ﺩ.ﺇ4,211 for 5 nights
4.98 out of 5 average rating, 99 reviews
Top guest favorite
Apartment in Chestertown
Waterfront historic district 1BR Apartment
1 king bed
Aug 29 – Sep 3
ﺩ.ﺇ3,750 for 5 nights
5.0 out of 5 average rating, 118 reviews
Guest favorite
Guesthouse in Chestertown
Cozy Carriage House
1 queen bed
Aug 16 – 21
ﺩ.ﺇ2,497 for 5 nights
4.89 out of 5 average rating, 179 reviews
Guest favorite
Home in Chestertown
Charming Haven on High
3 beds
Aug 20 – 25
ﺩ.ﺇ4,887 for 5 nights
4.97 out of 5 average rating, 33 reviews
Top guest favorite
Home in Chestertown
Cozy 3-bedroom home w/ Hot tub & firepit
3 queen beds
Aug 23 – 28
ﺩ.ﺇ4,538 for 5 nights
4.97 out of 5 average rating, 137 reviews
Top guest favorite
Guest suite in Chestertown
Chestertown - Eastern Shore Getaway
2 beds
Aug 26 – 31
ﺩ.ﺇ2,807 for 5 nights
4.98 out of 5 average rating, 168 reviews
Top guest favorite
Home in Chestertown
Totally Renovated historic house near town center
5 beds
Aug 17 – 22
ﺩ.ﺇ7,863 for 5 nights
5.0 out of 5 average rating, 202 reviews
Top guest favorite
Home in Chestertown
High Tide & Hound
3 beds
Sep 14 – 19
ﺩ.ﺇ3,552 for 5 nights
4.96 out of 5 average rating, 24 reviews
Top guest favorite
Home in Chestertown
2 Beds, 2.5 Baths - Perfect Downtown Location
2 queen beds
Aug 26 – 31
ﺩ.ﺇ5,829 for 5 nights
4.97 out of 5 average rating, 94 reviews
Top guest favorite
Farm stay in Chestertown
Blue Heron Farm Waterfront Chalet
4 beds
Aug 17 – 22
ﺩ.ﺇ6,996 for 5 nights
4.94 out of 5 average rating, 164 reviews
Room in Chestertown
Stay with OksanaHosting for 8 years,
Private Bedroom and bath in Chestertown, MD
Aug 15 – 20
ﺩ.ﺇ1,852 for 5 nights
4.87 out of 5 average rating, 144 reviews
Top guest favorite
Home in Chestertown
Down by the River
5 beds
Sep 2 – 7
ﺩ.ﺇ13,281 for 5 nights
5.0 out of 5 average rating, 44 reviews
Top guest favorite
Guest suite in Chestertown
House On The Hill - Historic Private Second Floor
3 beds
Sep 14 – 19
ﺩ.ﺇ2,373 for 5 nights
4.99 out of 5 average rating, 100 reviews
Guest favorite
Home in Chestertown
Holiday Escape to the Riverside
8 beds
Aug 24 – 29
ﺩ.ﺇ9,170 for 5 nights
5.0 out of 5 average rating, 23 reviews
Top guest favorite
Guest suite in Chestertown
Beautiful Waterfront Chestertown Getaway
2 beds
Nov 12 – 17
ﺩ.ﺇ3,354 for 5 nights
4.99 out of 5 average rating, 230 reviews
Top guest favorite
Guest suite in Chestertown
Historic Downtown Garden Oasis with Private Patio
1 queen bed
Aug 24 – 29
ﺩ.ﺇ3,285 for 5 nights
4.96 out of 5 average rating, 77 reviews
Guest favorite
Cottage in Centreville
Captain’s Quarters - Unique home on Corsica River!
2 beds
Aug 17 – 22
ﺩ.ﺇ3,983 for 5 nights
4.94 out of 5 average rating, 48 reviews