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Search results; Over 1,000 homes in Chester

Top guest favourite
Flat in Chester
The Millhouse Downtown Chester
2 bedrooms, 2 beds, 1.5 private bathrooms
16–21 Aug
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4.99 out of 5 average rating, 117 reviews
Guest favourite
Flat in Chester
Chester Village 'Pied-à-terre' above art gallery
1 bedroom, 3 beds, 1 bathroom
26–31 Jul
4.91 out of 5 average rating, 428 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, 65 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
Charming Chester Retreat - Cottage
2 bedrooms, 2 queen beds, 1 bathroom
2–7 Aug
4.98 out of 5 average rating, 197 reviews
Top guest favourite
Loft in Chester
The Village Loft: UNIQUE 1 BDRM W/ PRIVATE DECK
1 bedroom, 2 beds, 1 bathroom
19–24 Jul
4.98 out of 5 average rating, 185 reviews
Guest favourite
Cottage in Chester
Updated cottage "Beriozka" on Cedar Lake
2 bedrooms, 3 beds, 1 bathroom
10–15 Oct
4.97 out of 5 average rating, 309 reviews
Top guest favourite
Flat in Chester
Second floor River view apartment with EV charger
1 bedroom, 1 queen bed, 1 bathroom
12–17 Nov
5.0 out of 5 average rating, 46 reviews
Guest favourite
Tiny home in Deep River
Her tiny Parisian boat house
1 bedroom, 1 single bed, 2 bathrooms
19–24 Jul
4.92 out of 5 average rating, 48 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
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
Top guest favourite
Room in Deep River
Riverwind Willow Room in Deep River
1 queen bed, 1 bathroom
20–25 Aug
4.98 out of 5 average rating, 44 reviews
Guest favourite
Home in East Haddam
Historic House by the River
3 bedrooms, 4 beds, 1.5 bathrooms
26–31 Jul
4.9 out of 5 average rating, 71 reviews
Home in Old Lyme
Stoneacre at Point O'Woods
2 bedrooms, 2 queen beds, 2 bathrooms
9–14 Aug
Top guest favourite
Home in Clinton
The Connecticut Cottage | Historic Modern Charm
2 bedrooms, 2 beds, 2 bathrooms
1–6 Aug
5.0 out of 5 average rating, 18 reviews
Guest favourite
Cottage in East Haddam
Direct Waterfront Cottage on Moodus Reservoir.
3 bedrooms, 4 beds, 2 bathrooms
6–11 Oct
4.88 out of 5 average rating, 172 reviews
Top guest favourite
Tiny home in Deep River
Safari inspired little house
1 bedroom, 1 single bed, 1 bathroom
30 Jul – 4 Aug
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Tiny home in East Lyme
Waterfront Bliss Tiny Home
1 bedroom, 1 bed, 1 bathroom
2–7 Aug
4.99 out of 5 average rating, 159 reviews