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Search results; Over 1,000 homes in Chester

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Home in Chester
Stunning Artisan Waterfall Escape, Walk Downtown
2 bedrooms, 3 beds, 3 private bathrooms
1–6 Dec
,
4.96 out of 5 average rating, 221 reviews
Guest favourite
Flat in Chester
Chester Village 'Pied-à-terre' above art gallery
1 bedroom, 3 beds
19–24 Jul
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
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
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
2–7 Aug
4.97 out of 5 average rating, 63 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, 46 reviews
Top guest favourite
Loft in Chester
The Village Loft: UNIQUE 1 BDRM W/ PRIVATE DECK
1 bedroom, 2 beds
17–22 Jul
4.98 out of 5 average rating, 184 reviews
Top guest favourite
Cottage in Chester
Updated cottage "Beriozka" on Cedar Lake
2 bedrooms, 3 beds
10–15 Oct
4.97 out of 5 average rating, 308 reviews
Top guest favourite
Room in Chester
Comfy Artist View at Chester Village
1 king bed
1–6 Aug
4.96 out of 5 average rating, 191 reviews
Guest favourite
Home in East Haddam
Historic House by the River
3 bedrooms, 4 beds
26–31 Jul
4.9 out of 5 average rating, 71 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, 116 reviews
Guest favourite
Tiny home in Deep River
Her tiny Parisian boat house
1 bedroom, 1 single bed
19–24 Jul
4.91 out of 5 average rating, 46 reviews
Guest favourite
Home in Chester
Charmingly Chester on the Great Brook and Pond
4 bedrooms, 4 double beds
14–19 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
2–7 Aug
4.92 out of 5 average rating, 76 reviews
Top guest favourite
Room in Deep River
Riverwind Willow Room in Deep River
1 queen bed
16–21 Aug
4.98 out of 5 average rating, 44 reviews
Guest favourite
Home in East Haddam
East Haddam Village | Walkable, Pet Friendly
4 bedrooms, 4 beds
13–18 Jul
4.9 out of 5 average rating, 52 reviews
Top guest favourite
Home in Essex
Bushy Hill House
3 bedrooms, 4 beds
27 Aug – 1 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Haddam
Charming 1806 farm house close to the CT River.
5 bedrooms, 7 beds
20–25 Sept
4.92 out of 5 average rating, 156 reviews
Top guest favourite
Home in Clinton
“11:11” 🙏 Updated Stylish Retreat 🌊 2 Mi To Beach
4 bedrooms, 5 beds
17–22 Jul
4.95 out of 5 average rating, 85 reviews