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Search results; Over 1,000 homes in Chester

Top guest favourite
Loft in Chester
The Village Loft: UNIQUE 1 BDRM W/ PRIVATE DECK
1 bedroom, 2 beds, 1 private bathroom
28 Sept – 3 Oct
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4.98 out of 5 average rating, 190 reviews
Top guest favourite
Home in Chester
Chester Gingerbread House: Stroll to Village
3 bedrooms, 3 beds, 2.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 47 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, 434 reviews
Home in Chester
Historic 1836 Toll House on Brook – Walk to Town
2 bedrooms, 3 beds, 1.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Room in Chester
Comfy Artist View at Chester Village
1 king bed, 1 bathroom
18–23 Sept
4.96 out of 5 average rating, 198 reviews
Top guest favourite
Cottage in Chester
Updated cottage "Beriozka" on Cedar Lake
2 bedrooms, 3 beds, 1 bathroom
19–24 Oct
4.97 out of 5 average rating, 313 reviews
Top guest favourite
Flat in Chester
The Little Chestnut: Walk to downtown Chester.
2 bedrooms, 3 beds, 1 bathroom
11–16 Oct
4.97 out of 5 average rating, 74 reviews
Top guest favourite
Flat in Chester
Charming Chester Retreat - Cottage
2 bedrooms, 2 queen beds, 1 bathroom
4–9 Oct
4.99 out of 5 average rating, 203 reviews
Top guest favourite
Flat in Chester
The Millhouse Downtown Chester
2 bedrooms, 2 queen beds, 1.5 bathrooms
13–18 Sept
4.99 out of 5 average rating, 123 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, 54 reviews
Top guest favourite
Flat in Deep River
Lovely Garden-Level Apartment in Heart of Town
2 bedrooms, 2 beds, 1 bathroom
25–30 Oct
4.94 out of 5 average rating, 174 reviews
Top guest favourite
Room in Deep River
Riverwind Willow Room in Deep River
1 queen bed, 1 bathroom
4–9 Oct
4.98 out of 5 average rating, 62 reviews
Guest favourite
Home in Chester
Charmingly Chester on the Great Brook and Pond
4 bedrooms, 4 double beds, 2.5 bathrooms
11–16 Sept
4.83 out of 5 average rating, 76 reviews
Guest favourite
Home in East Haddam
Historic House by the River
3 bedrooms, 4 beds, 1.5 bathrooms
13–18 Sept
4.91 out of 5 average rating, 76 reviews
Guest favourite
Cottage in East Haddam
Direct Waterfront Cottage on Moodus Reservoir.
3 bedrooms, 4 beds, 2 bathrooms
9–14 Nov
4.89 out of 5 average rating, 175 reviews
Guest favourite
Flat in East Haddam
Walk To Goodspeed Opera House!
2 bedrooms, 2 king beds, 1 bathroom
9–14 Sept
4.9 out of 5 average rating, 83 reviews
Guest favourite
Flat in Haddam
Welcome home! Cozy Apartment in Haddam
2 bedrooms, 2 beds, 1 bathroom
11–16 Sept
5.0 out of 5 average rating, 10 reviews
Guest favourite
Guest house in Clinton
Clinton's Secret, Beach Pass, Pet Friendly
2 bedrooms, 2 beds, 2.5 bathrooms
10–15 Sept
4.97 out of 5 average rating, 29 reviews
Guest favourite
Home in East Haddam
East Haddam Village | Walkable, Pet Friendly
4 bedrooms, 4 beds, 1.5 bathrooms
12–17 Sept
4.9 out of 5 average rating, 60 reviews