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Search results; Over 1,000 homes in Chester

Top guest favourite
Loft in Chester
The Village Loft: UNIQUE 1 BDRM W/ PRIVATE DECK
1 bedroom, 2 beds, 1 private bathroom
17–22 Jul
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4.98 out of 5 average rating, 184 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
29 Jul – 3 Aug
4.98 out of 5 average rating, 196 reviews
Guest favourite
Flat in Chester
Chester Village 'Pied-à-terre' above art gallery
1 bedroom, 3 beds, 1 bathroom
19–24 Jul
4.92 out of 5 average rating, 427 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, 62 reviews
Top guest favourite
Flat in Chester
Second floor River view apartment with EV charger
1 bedroom, 1 queen bed, 1 bathroom
8–13 Oct
5.0 out of 5 average rating, 46 reviews
Top 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, 307 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 Chester
The Millhouse Downtown Chester
2 bedrooms, 2 queen beds, 1.5 bathrooms
16–21 Aug
4.99 out of 5 average rating, 115 reviews
Top guest favourite
Room in Deep River
Riverwind Willow Room in Deep River
1 queen bed, 1 bathroom
16–21 Aug
4.98 out of 5 average rating, 42 reviews
Guest favourite
Tiny home in Deep River
Her tiny Parisian boat house
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
Historic House by the River
3 bedrooms, 4 beds, 1.5 bathrooms
26–31 Jul
4.9 out of 5 average rating, 71 reviews
Top guest favourite
Tiny home in Deep River
Safari inspired little house
1 bedroom, 1 single bed, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Chester
Charmingly Chester on the Great Brook and Pond
4 bedrooms, 4 double beds, 2.5 bathrooms
10–15 Jul
4.82 out of 5 average rating, 74 reviews
Guest favourite
Flat in East Haddam
Walk To Goodspeed Opera House!
2 bedrooms, 2 king beds, 1 bathroom
2–7 Aug
4.92 out of 5 average rating, 75 reviews
Guest favourite
Home in East Haddam
East Haddam Village | Walkable, Pet Friendly
4 bedrooms, 4 beds, 1.5 bathrooms
13–18 Jul
4.9 out of 5 average rating, 52 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, 171 reviews
Guest favourite
Barn in Killingworth
Experience Yellowstone (aka) Fortunato Farm
3 bedrooms, 1 queen bed, 2 bathrooms
9–14 Jul
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Room in Deep River
Hedy's Hippy home
1 bathroom
23–28 Jul
4.96 out of 5 average rating, 53 reviews