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Search results; Over 1,000 homes in Chester

Top guest favourite
Cottage in Chester
Updated cottage "Beriozka" on Cedar Lake
2 bedrooms, 3 beds, 1 private bathroom
10–15 Oct
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4.97 out of 5 average rating, 310 reviews
Guest favourite
Flat in Chester
Chester Village 'Pied-à-terre' above art gallery
1 bedroom, 3 beds, 1 bathroom
13–18 Sept
4.91 out of 5 average rating, 432 reviews
Top guest favourite
Flat in Chester
The Little Chestnut: Walk to downtown Chester.
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.97 out of 5 average rating, 69 reviews
Home in Chester
Historic 1836 Toll House on Brook – Walk to Town
2 bedrooms, 3 beds, 1.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Loft in Chester
The Village Loft: UNIQUE 1 BDRM W/ PRIVATE DECK
1 bedroom, 2 beds, 1 bathroom
16–21 Aug
4.98 out of 5 average rating, 189 reviews
Top guest favourite
Home in Chester
Chester Gingerbread House: Stroll to Village
3 bedrooms, 3 beds, 2.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 44 reviews
Top guest favourite
Flat in Chester
Charming Chester Retreat - Cottage
2 bedrooms, 2 queen beds, 1 bathroom
19–24 Sept
4.99 out of 5 average rating, 201 reviews
Guest favourite
Room in Deep River
Safari inspired little house
2 single beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 23 reviews
Top guest favourite
Room in Chester
Comfy Artist View at Chester Village
1 king bed, 1 bathroom
17–22 Aug
4.96 out of 5 average rating, 197 reviews
Top guest favourite
Room in Deep River
Riverwind Hearts & Flowers Room in Deep River
1 queen bed, 1 bathroom
22–27 Aug
4.97 out of 5 average rating, 35 reviews
Top guest favourite
Flat in Deep River
Lovely Garden-Level Apartment in Heart of Town
2 bedrooms, 2 beds, 1 bathroom
13–18 Oct
4.94 out of 5 average rating, 172 reviews
Guest favourite
Home in Chester
Charmingly Chester on the Great Brook and Pond
4 bedrooms, 4 double beds, 2.5 bathrooms
18–23 Aug
4.83 out of 5 average rating, 76 reviews
Top guest favourite
Room in Deep River
Hippy home
2 double beds, 1 bathroom
27 Aug – 1 Sept
4.96 out of 5 average rating, 55 reviews
Top guest favourite
Flat in Chester
The Millhouse Downtown Chester
2 bedrooms, 2 queen beds, 1.5 bathrooms
16–21 Aug
4.99 out of 5 average rating, 120 reviews
Top guest favourite
Flat in Chester
Second floor River view apartment with EV charger
1 bedroom, 1 queen bed, 1 bathroom
12–17 Nov
5.0 out of 5 average rating, 50 reviews
Guest favourite
Home in Essex
Historic Essex Home w/ Large Yard Near Downtown!
2 bedrooms, 3 beds, 1.5 bathrooms
30 Sept – 5 Oct
4.91 out of 5 average rating, 139 reviews
Flat in Middletown
Cozy In-law near Wesleyan - clean and private
1 bedroom, 2 beds, 1 bathroom
18–23 Aug
New place to stay
Top guest favourite
Cabin in Colchester
The Colchester Cottage
1 bedroom, 3 beds, 1 bathroom
25–30 Oct
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Guest house in Portland
Guesthouse Farm Stay
1 bedroom, 2 beds, 1 bathroom
31 Oct – 5 Nov
4.98 out of 5 average rating, 342 reviews