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Search results; Over 1,000 homes in Chester

Descriptions are based on details hosts provide
Superhost
Home in Chester
Stunning Artisan Waterfall Escape, Walk Downtown
2 bedrooms, 3 beds, 3 private bathrooms
1–6 Dec
,
4.96 out of 5 average rating, 221 reviews
Guest favourite
Flat in Chester
High ceilings above an art gallery
1 bedroom, 3 beds, 1 bathroom
19–24 Jul
4.92 out of 5 average rating, 427 reviews
Top guest favourite
Flat in Chester
Historic hideaway above a bookstore
2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
4.97 out of 5 average rating, 64 reviews
Home in Chester
Historic 1836 Toll House on Brook – Walk to Town
2 bedrooms, 3 beds, 1.5 bathrooms
7–12 Sept
New place to stay
Top guest favourite
Flat in Chester
Wood-burning fireplace and a roof deck
2 bedrooms, 2 queen beds, 1 bathroom
29 Jul – 3 Aug
4.98 out of 5 average rating, 197 reviews
Top guest favourite
Flat in Chester
River waterfront with kayaks and a dock
1 bedroom, 1 queen bed, 1 bathroom
12–17 Nov
5.0 out of 5 average rating, 46 reviews
Top guest favourite
Home in Chester
Whimsical Victorian a stroll from downtown
3 bedrooms, 3 beds, 2.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 44 reviews
Top guest favourite
Loft in Chester
The Village Loft: UNIQUE 1 BDRM W/ PRIVATE DECK
1 bedroom, 2 beds, 1 bathroom
17–22 Jul
4.98 out of 5 average rating, 184 reviews
Guest favourite
Tiny home in Deep River
Her tiny Parisian boat house
1 bedroom, 1 single bed, 2 bathrooms
19–24 Jul
4.91 out of 5 average rating, 46 reviews
Top guest favourite
Room in Chester
Federal colonial, 2-minute walk to village
1 king bed, 1 bathroom
1–6 Aug
4.96 out of 5 average rating, 191 reviews
Top guest favourite
Room in Deep River
1854 colonial home in the River Valley
1 queen bed, 1 bathroom
16–21 Aug
4.98 out of 5 average rating, 44 reviews
Top guest favourite
Flat in Deep River
Lovely Garden-Level Apartment in Heart of Town
2 bedrooms, 2 beds, 1 bathroom
18–23 Aug
4.94 out of 5 average rating, 172 reviews
Top guest favourite
Flat in Westbrook
Meadowview & Pondside Retreat
1 bedroom, 1 queen bed, 1 bathroom
30 Aug – 4 Sept
4.96 out of 5 average rating, 49 reviews
Guest favourite
Cottage in Chester
Cathedral ceilings and a lakeside fire pit
2 bedrooms, 3 beds, 1 bathroom
10–15 Oct
4.97 out of 5 average rating, 309 reviews
Top guest favourite
Tiny home in Deep River
Safari inspired little house
1 bedroom, 1 single bed, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Cottage in Deep River
Country Cottage in Private Garden Setting
2 bedrooms, 2 beds, 2 bathrooms
17–22 Aug
4.91 out of 5 average rating, 103 reviews
Flat in Haddam
Welcome home! Cozy Apartment in Haddam
2 bedrooms, 2 beds, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 4 reviews
Guest favourite
Flat in Clinton
Skylit loft 10 minutes from the beach
1 bed, 1 bathroom
19–24 Jul
4.9 out of 5 average rating, 92 reviews
Flat in East Haddam
Renovated historic New England home with fireplace
2 bedrooms, 2 queen beds, 1 bathroom
20–25 Jul
New place to stay