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Search results; 289 homes in Chestertown

Top guest favourite
Home in Chestertown
2 Beds, 2.5 Baths - Perfect Downtown Location
2 bedrooms, 2 beds, 2.5 private bathrooms
20–25 Sept
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4.98 out of 5 average rating, 126 reviews
Top guest favourite
Home in Chestertown
The Garden Estate: Historic Town Center Home
5 bedrooms, 6 beds
20–25 Sept
5.0 out of 5 average rating, 253 reviews
Top guest favourite
Flat in Chestertown
Carriage House Studio -Secluded "Treehouse" Escape
2 king beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 301 reviews
Top guest favourite
Home in Chestertown
High Tide & Hound
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 101 reviews
Top guest favourite
Home in Chestertown
Cozy 3-bedroom home w/ Hot tub & firepit
3 bedrooms, 3 queen beds
2–7 Nov
4.98 out of 5 average rating, 194 reviews
Top guest favourite
Home in Chestertown
Charming Haven on High
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.96 out of 5 average rating, 79 reviews
Top guest favourite
Home in Chestertown
Classic Victorian in Chestertown
4 bedrooms, 8 beds
12–17 Oct
4.96 out of 5 average rating, 139 reviews
Top guest favourite
Guest suite in Chestertown
House On The Hill - Historic Private Second Floor
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.99 out of 5 average rating, 145 reviews
Top guest favourite
Flat in Chestertown
Bright, new apartment in the heart of Chestertown
2 bedrooms, 2 beds
20–25 Sept
4.98 out of 5 average rating, 144 reviews
Top guest favourite
Home in Chestertown
Lovely Home in Chestertown With Free EV Charging
3 bedrooms, 4 beds
20–25 Sept
5.0 out of 5 average rating, 101 reviews
Top guest favourite
Home in Chestertown
The Patriot House-Chestertown, MD
6 bedrooms, 7 beds
27 Sept – 2 Oct
4.96 out of 5 average rating, 135 reviews
Guest favourite
Home in Chestertown
Waterfront Paradise w/ Pier - kayak to Chestertown
3 bedrooms, 7 beds
20–25 Sept
4.91 out of 5 average rating, 67 reviews
Guest favourite
Home in Chestertown
River front cottage with private dock & water fun
5 bedrooms, 11 beds
28 Sept – 3 Oct
4.96 out of 5 average rating, 105 reviews
Top guest favourite
Home in Chestertown
Magnolia House is for sale! Historic Chestertown
3 bedrooms, 4 beds
20–25 Sept
4.98 out of 5 average rating, 63 reviews
Top guest favourite
Guest suite in Chestertown
Beautiful Waterfront Chestertown Getaway
1 bedroom, 2 beds
8–13 Dec
4.99 out of 5 average rating, 255 reviews
Top guest favourite
Home in Chestertown
Primrose Cottage~Walk to Downtown Chestertown
3 bedrooms, 4 beds
14–19 Sept
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Chestertown
Heart of Historic Chestertown - Church Alley
2 bedrooms, 2 queen beds
2–7 Nov
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Loft in Chestertown
Loft at Fountain Park - Prime Downtown Location
4 bedrooms, 5 beds
20–25 Sept
4.94 out of 5 average rating, 93 reviews
Guest favourite
Home in Chestertown
Relaxing Waterfront - Golf Course & Sunset Views
3 bedrooms, 6 beds
4–9 Oct
4.92 out of 5 average rating, 39 reviews