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Search results; Over 1,000 homes in Chester

Descriptions are based on details hosts provide
Guest favourite
Flat in Chester
Chester Village 'Pied-à-terre' above art gallery
1 bedroom, 3 beds, 1 shared bathroom
19–24 Jul
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4.92 out of 5 average rating, 427 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
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
The Little Chestnut.
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
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
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
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
Room in Chester
Comfy Artist View at Chester Village
1 king bed, 1 bathroom
1–6 Aug
4.96 out of 5 average rating, 191 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
Guest favourite
Tiny home in Deep River
An artist escape with a pool
1 bedroom, 1 single bed, 2 bathrooms
19–24 Jul
4.91 out of 5 average rating, 46 reviews
Guest favourite
Home in East Haddam
1800s charm with Connecticut River views
3 bedrooms, 4 beds, 1.5 bathrooms
26–31 Jul
4.9 out of 5 average rating, 71 reviews
Top guest favourite
Flat in Chester
Historic millhouse with a waterfall and fire pit
2 bedrooms, 2 queen beds, 1.5 bathrooms
16–21 Aug
4.99 out of 5 average rating, 117 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
Guest favourite
Home in Chester
Charmingly Chester on the Great Brook and Pond
4 bedrooms, 4 double beds, 2.5 bathrooms
17–22 Jul
4.83 out of 5 average rating, 75 reviews
Guest favourite
Flat in East Haddam
Walk To Goodspeed Opera House!
2 bedrooms, 2 king beds, 1 bathroom
17–22 Aug
4.92 out of 5 average rating, 76 reviews
Guest favourite
Home in East Haddam
1850 farmhouse near the Connecticut River
4 bedrooms, 4 beds, 1.5 bathrooms
25–30 Jul
4.91 out of 5 average rating, 53 reviews
Top guest favourite
Tiny home in Deep River
Safari-inspired retreat in the woods
1 bedroom, 1 single bed, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 12 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