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Search results; Over 1,000 homes in Chester

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, 309 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
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
Top guest favourite
Flat in Chester
The Little Chestnut.
4.97 out of 5 average rating, 65 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Top guest favourite
Flat in Chester
Charming Chester Retreat - Cottage
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
Loft in Chester
The Village Loft: UNIQUE 1 BDRM W/ PRIVATE DECK
4.98 out of 5 average rating, 184 reviews, 1 bedroom, 2 beds, 1 bathroom
17–22 Jul
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
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
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
Guest favourite
Tiny home in Deep River
Her tiny Parisian boat house
4.91 out of 5 average rating, 47 reviews, 1 bedroom, 1 bed, 2 bathrooms
19–24 Jul
Top guest favourite
Room in Deep River
Riverwind Willow Room in Deep River
4.98 out of 5 average rating, 44 reviews, 1 queen bed, 1 bathroom
20–25 Aug
Guest favourite
Home in East Haddam
Historic House by the River
4.9 out of 5 average rating, 71 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
26–31 Jul
Guest favourite
Cabin in Colchester
The Colchester Cottage
5.0 out of 5 average rating, 6 reviews, 1 bedroom, 3 beds, 1 bathroom
12–17 Oct
Top guest favourite
Tiny home in Deep River
Safari inspired little house
5.0 out of 5 average rating, 13 reviews, 1 bedroom, 1 bed, 1 bathroom
30 Jul – 4 Aug
Top guest favourite
Flat in Chester
The Millhouse Downtown Chester
4.99 out of 5 average rating, 117 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
16–21 Aug
Top guest favourite
Home in Clinton
The Connecticut Cottage | Historic Modern Charm
5.0 out of 5 average rating, 18 reviews, 2 bedrooms, 2 beds, 2 bathrooms
1–6 Aug
Top guest favourite
Cottage in East Haddam
Historic Hearthstone Cottage
5.0 out of 5 average rating, 106 reviews, 1 bedroom, 3 beds, 1 bathroom
23–28 Aug
Guest favourite
Cottage in East Haddam
Direct Waterfront Cottage on Moodus Reservoir.
4.88 out of 5 average rating, 172 reviews, 3 bedrooms, 4 beds, 2 bathrooms
6–11 Oct