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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
Home in Chester
Historic 1836 Toll House on Brook – Walk to Town
2 bedrooms, 3 beds
7–12 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Chester
Chester Gingerbread House: Stroll to Village
3 bedrooms, 3 beds
26–31 Aug
5.0 out of 5 average rating, 44 reviews
Top guest favourite
Flat in Chester
The Little Chestnut: Walk to downtown Chester.
2 bedrooms, 3 beds
16–21 Aug
4.97 out of 5 average rating, 67 reviews
Guest favourite
Flat in Chester
Chester Village 'Pied-à-terre' above art gallery
1 bedroom, 3 beds
17–22 Aug
4.91 out of 5 average rating, 431 reviews
Top guest favourite
Flat in Chester
Charming Chester Retreat - Cottage
2 bedrooms, 2 queen beds
17–22 Aug
4.99 out of 5 average rating, 201 reviews
Top guest favourite
Loft in Chester
The Village Loft: UNIQUE 1 BDRM W/ PRIVATE DECK
1 bedroom, 2 beds
16–21 Aug
4.98 out of 5 average rating, 187 reviews
Top guest favourite
Flat in Deep River
Lovely Garden-Level Apartment in Heart of Town
2 bedrooms, 2 beds
13–18 Oct
4.94 out of 5 average rating, 172 reviews
Top guest favourite
Room in Chester
Comfy Artist View at Chester Village
1 king bed
20–25 Sept
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
22–27 Aug
4.97 out of 5 average rating, 34 reviews
Top guest favourite
Room in Deep River
Safari inspired little house
2 single beds
13–18 Aug
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Flat in Chester
The Millhouse Downtown Chester
2 bedrooms, 2 queen beds
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
12–17 Nov
5.0 out of 5 average rating, 50 reviews
Top guest favourite
Home in East Haddam
Historic House by the River
3 bedrooms, 4 beds
21–26 Aug
4.91 out of 5 average rating, 74 reviews
Top guest favourite
Home in Clinton
The Connecticut Cottage | Historic Modern Charm
2 bedrooms, 2 beds
23–28 Aug
4.95 out of 5 average rating, 22 reviews
Guest favourite
Cottage in East Haddam
Direct Waterfront Cottage on Moodus Reservoir.
3 bedrooms, 4 beds
9–14 Nov
4.88 out of 5 average rating, 172 reviews
Superhost
Flat in Essex
Historic 2 BR, quick walk to downtown Essex!
2 bedrooms, 2 beds
16–21 Aug
Guest favourite
Guest house in Clinton
Clinton's Secret, Beach Pass, Pet Friendly
2 bedrooms, 2 beds
23–28 Aug
4.96 out of 5 average rating, 28 reviews
Guest favourite
Flat in East Haddam
Walk To Goodspeed Opera House!
2 bedrooms, 2 king beds
28 Sept – 3 Oct
4.91 out of 5 average rating, 81 reviews