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Search results; 304 homes in Chestertown

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Guest suite in Chestertown
Beautiful Waterfront Chestertown Getaway
1 bedroom, 2 beds, 1 private bathroom
2–7 Nov
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4.99 out of 5 average rating, 251 reviews
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Flat in Chestertown
Carriage House Studio -Secluded "Treehouse" Escape
4.97 out of 5 average rating, 286 reviews, 2 beds, 1 bathroom
16–21 Aug
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Home in Chestertown
Harbor View Haven | Waterfront w/ Hot Tub + Dock!
4.96 out of 5 average rating, 112 reviews, 3 bedrooms, 6 beds, 2 bathrooms
23–28 Aug
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Home in Chestertown
High Tide & Hound
4.98 out of 5 average rating, 85 reviews, 2 bedrooms, 3 beds, 2 bathrooms
2–7 Aug
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Home in Chestertown
The Garden Estate: Historic Town Center Home
5.0 out of 5 average rating, 244 reviews, 5 bedrooms, 6 beds, 4 bathrooms
25–30 Aug
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Home in Chestertown
Charming Haven on High
4.96 out of 5 average rating, 69 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
2–7 Aug
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Home in Chestertown
Cozy 3-bedroom home w/ Hot tub & firepit
4.98 out of 5 average rating, 181 reviews, 3 bedrooms, 3 beds, 2 bathrooms
15–20 Aug
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Home in Chestertown
Lovely Home in Chestertown With Free EV Charging
5.0 out of 5 average rating, 96 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
14–19 Sept
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Home in Chestertown
Heart of Historic Chestertown - Church Alley
5.0 out of 5 average rating, 15 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
10–15 Aug
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Home in Chestertown
River front cottage with private dock & water fun
4.96 out of 5 average rating, 105 reviews, 5 bedrooms, 11 beds, 3 bathrooms
28 Sept – 3 Oct
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Home in Chestertown
Still Waters River House
5.0 out of 5 average rating, 9 reviews, 4 bedrooms, 7 beds, 2 bathrooms
1–6 Sept
Home in Chestertown
Quiet, Shabby-chic home in downtown Chestertown
4.93 out of 5 average rating, 27 reviews, 2 bedrooms, 2 beds, 2 bathrooms
1–6 Aug
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114 High - Upper Floors Apt Chestertown Sleeps 7
5.0 out of 5 average rating, 16 reviews, 3 bedrooms, 5 beds, 2 bathrooms
1–6 Aug
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Guest suite in Chestertown
House On The Hill - Historic Private Second Floor
4.99 out of 5 average rating, 137 reviews, 2 bedrooms, 3 beds, 1 bathroom
10–15 Aug
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Townhouse in Chestertown
Pole Pole House - Downtown Chestertown Retreat
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 3 beds, 1 bathroom
1–6 Aug
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Bright, new apartment in the heart of Chestertown
4.98 out of 5 average rating, 141 reviews, 2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
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Home in Chestertown
2 Beds, 2.5 Baths - Perfect Downtown Location
4.98 out of 5 average rating, 123 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
1–6 Aug
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Home in Chestertown
Relaxing Waterfront - Golf Course & Sunset Views
4.97 out of 5 average rating, 35 reviews, 3 bedrooms, 6 beds, 3 bathrooms
17–22 Aug
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Home in Chestertown
Waterfront Paradise w/ Pier - kayak to Chestertown
4.91 out of 5 average rating, 66 reviews, 3 bedrooms, 7 beds, 2 bathrooms
26–31 Aug