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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
Chester Village 'Pied-à-terre' above art gallery
4.92 out of 5 average rating, 427 reviews, 1 bedroom, 3 beds, 1 bathroom
19–24 Jul
Top guest favourite
Flat in Chester
Historic hideaway above a bookstore
4.97 out of 5 average rating, 64 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Top guest favourite
Flat in Chester
Wood-burning fireplace and a roof deck
4.98 out of 5 average rating, 197 reviews, 2 bedrooms, 2 beds, 1 bathroom
29 Jul – 3 Aug
Home in Chester
Historic 1836 Toll House on Brook – Walk to Town
New place to stay, 2 bedrooms, 3 beds, 1.5 bathrooms
7–12 Sept
Top guest favourite
Flat in Chester
Second floor River view apartment with EV charger
5.0 out of 5 average rating, 46 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Nov
Top guest favourite
Home in Chester
Chester Gingerbread House: Stroll to Village
5.0 out of 5 average rating, 44 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
7–12 Sept
Guest favourite
Tiny home in Deep River
Her tiny Parisian boat house
4.91 out of 5 average rating, 46 reviews, 1 bedroom, 1 bed, 2 bathrooms
19–24 Jul
Top guest favourite
Loft in Chester
Historic loft with a private deck
4.98 out of 5 average rating, 184 reviews, 1 bedroom, 2 beds, 1 bathroom
17–22 Jul
Top guest favourite
Room in Chester
Comfy Artist View at Chester Village
4.96 out of 5 average rating, 191 reviews, 1 king bed, 1 bathroom
1–6 Aug
Top guest favourite
Room in Deep River
1854 colonial home in the River Valley
4.98 out of 5 average rating, 44 reviews, 1 queen bed, 1 bathroom
16–21 Aug
Top guest favourite
Flat in Westbrook
Meadowview & Pondside Retreat
4.96 out of 5 average rating, 49 reviews, 1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Cottage in Chester
Cathedral ceilings and a lakeside fire pit
4.97 out of 5 average rating, 309 reviews, 2 bedrooms, 3 beds, 1 bathroom
10–15 Oct
Top guest favourite
Flat in Deep River
Lovely Garden-Level Apartment in Heart of Town
4.94 out of 5 average rating, 172 reviews, 2 bedrooms, 2 beds, 1 bathroom
18–23 Aug
Top guest favourite
Tiny home in Deep River
Safari-inspired retreat in the woods
5.0 out of 5 average rating, 12 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Jul
Flat in Haddam
Welcome home! Cozy Apartment in Haddam
5.0 out of 5 average rating, 4 reviews, 2 bedrooms, 2 beds, 1 bathroom
19–24 Jul
Top guest favourite
Cottage in Deep River
Country Cottage in Private Garden Setting
4.91 out of 5 average rating, 103 reviews, 2 bedrooms, 2 beds, 2 bathrooms
17–22 Aug
Guest favourite
Flat in Clinton
Bright & Cozy Loft Near Beach
4.9 out of 5 average rating, 92 reviews, 1 bed, 1 bathroom
19–24 Jul
Top guest favourite
Room in Deep River
Shared pool and garden near the river
4.96 out of 5 average rating, 53 reviews, 1 bathroom
23–28 Jul