Search results; 295 places in Chestertown

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Guest favorite
Guest suite in Chestertown
Beautiful Waterfront Chestertown Getaway
2 guests1 bedroom2 beds1 bath
Sep 30 – Oct 5
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Sep 30 – Oct 5
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R15,518 ZAR for 5 nights

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Top guest favorite
Home in Chestertown
High Tide & Hound
3 beds
Aug 3 – 8
R17,653 ZAR for 5 nights
5.0 out of 5 average rating, 17 reviews
Guest favorite
Home in Chestertown
Charming Haven on High
3 beds
Jul 13 – 18
R19,344 ZAR for 5 nights
4.96 out of 5 average rating, 27 reviews
Top guest favorite
Apartment in Chestertown
Waterfront historic district 1BR Apartment
1 king bed
Jul 18 – 23
R18,414 ZAR for 5 nights
5.0 out of 5 average rating, 113 reviews
Top guest favorite
Guest suite in Chestertown
Chestertown - Eastern Shore Getaway
2 beds
Jul 19 – 24
R13,108 ZAR for 5 nights
4.98 out of 5 average rating, 165 reviews
Top guest favorite
Guest suite in Chestertown
House On The Hill - Historic Private Second Floor
3 beds
Jul 13 – 18
R11,628 ZAR for 5 nights
4.99 out of 5 average rating, 97 reviews
Top guest favorite
Apartment in Chestertown
Private cozy cottage - center of Chestertown .
1 king bed
Aug 10 – 15
R16,720 ZAR for 5 nights
4.96 out of 5 average rating, 237 reviews
Top guest favorite
Condo in Chestertown
Historic Loft w/ Park View & Spa Access
2 queen beds
Jul 9 – 14
R24,524 ZAR for 5 nights
5.0 out of 5 average rating, 25 reviews
Guest favorite
Guesthouse in Chestertown
Cozy Carriage House
1 queen bed
Aug 10 – 15
R10,571 ZAR for 5 nights
4.89 out of 5 average rating, 175 reviews
Top guest favorite
Apartment in Chestertown
Bright, new apartment in the heart of Chestertown
2 beds
Jul 18 – 23
R25,412 ZAR for 5 nights
4.98 out of 5 average rating, 95 reviews
Guest favorite
Home in Chestertown
Relaxing Waterfront - Golf Course & Sunset Views
6 beds
Aug 9 – 14
R30,528 ZAR for 5 nights
5.0 out of 5 average rating, 6 reviews
Top guest favorite
Guesthouse in Chestertown
Owl Cottage - Cozy, Private & Walkable to Town
2 beds
Aug 10 – 15
R21,036 ZAR for 5 nights
5.0 out of 5 average rating, 33 reviews
Top guest favorite
Home in Chestertown
Cozy 3-bedroom home w/ Hot tub & firepit
3 queen beds
Jul 26 – 31
R22,114 ZAR for 5 nights
4.97 out of 5 average rating, 132 reviews
Room in Chestertown
Stay with OksanaHosting for 8 years,
Private Bedroom and bath in Chestertown, MD
Jul 11 – 16
R9,091 ZAR for 5 nights
4.87 out of 5 average rating, 143 reviews
Top guest favorite
Farm stay in Chestertown
Blue Heron Farm Waterfront Chalet
4 beds
Jul 21 – 26
R34,883 ZAR for 5 nights
4.94 out of 5 average rating, 160 reviews
Guest favorite
Home in Chestertown
Holiday Escape to the Riverside
8 beds
Aug 17 – 22
R46,933 ZAR for 5 nights
5.0 out of 5 average rating, 20 reviews
Top guest favorite
Home in Chestertown
Totally Renovated historic house near town center
5 beds
Aug 17 – 22
R32,905 ZAR for 5 nights
5.0 out of 5 average rating, 199 reviews
Guest favorite
Home in Chestertown
NEW Chestertown Retreat
4 beds
Jul 29 – Aug 3
R23,784 ZAR for 5 nights
4.98 out of 5 average rating, 46 reviews
Guest favorite
Apartment in Chestertown
Cozy One Bed/One Bath Apartment in Chestertown
2 queen beds
Jul 20 – 25
R22,621 ZAR for 5 nights
5.0 out of 5 average rating, 17 reviews