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Search results; Over 1,000 homes in Chester

Top guest favourite
Flat in Chester
Charming Chester Retreat - Cottage
2 bedrooms, 2 beds, 1 shared bathroom
17–22 Aug
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4.98 out of 5 average rating, 198 reviews
Top guest favourite
Flat in Chester
The Little Chestnut: Walk to downtown Chester.
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
23–28 Aug
5.0 out of 5 average rating, 44 reviews
Guest favourite
Flat in Chester
Chester Village 'Pied-à-terre' above art gallery
1 bedroom, 3 beds, 1 bathroom
2–7 Aug
4.91 out of 5 average rating, 429 reviews
Home in Chester
Historic 1836 Toll House on Brook – Walk to Town
2 bedrooms, 3 beds, 1.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Loft in Chester
The Village Loft: UNIQUE 1 BDRM W/ PRIVATE DECK
1 bedroom, 2 beds, 1 bathroom
2–7 Aug
4.98 out of 5 average rating, 185 reviews
Top guest favourite
Flat in Deep River
Lovely Garden-Level Apartment in Heart of Town
2 bedrooms, 2 beds, 1 bathroom
13–18 Aug
4.94 out of 5 average rating, 172 reviews
Top guest favourite
Room in Chester
Comfy Artist View at Chester Village
1 king bed, 1 bathroom
20–25 Sept
4.96 out of 5 average rating, 195 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, 310 reviews
Top guest favourite
Room in Deep River
Riverwind Hearts & Flowers Room in Deep River
1 queen bed, 1 bathroom
16–21 Aug
4.97 out of 5 average rating, 31 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, 47 reviews
Guest favourite
Home in Chester
Charmingly Chester on the Great Brook and Pond
4 bedrooms, 4 double beds, 2.5 bathrooms
10–15 Aug
4.83 out of 5 average rating, 75 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, 118 reviews
Top guest favourite
Home in Clinton
The Connecticut Cottage | Historic Modern Charm
2 bedrooms, 2 beds, 2 bathrooms
23–28 Aug
4.95 out of 5 average rating, 20 reviews
Top guest favourite
Flat in East Haddam
Penny Corner Airbnb
1 bedroom, 2 beds, 1 bathroom
8–13 Aug
4.89 out of 5 average rating, 218 reviews
Top guest favourite
Tiny home in Deep River
Safari inspired little house
1 bedroom, 1 single bed, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 17 reviews
Guest favourite
Flat in East Haddam
Walk To Goodspeed Opera House!
2 bedrooms, 2 king beds, 1 bathroom
17–22 Aug
4.92 out of 5 average rating, 77 reviews
Guest favourite
Home in East Haddam
Historic House by the River
3 bedrooms, 4 beds, 1.5 bathrooms
16–21 Aug
4.9 out of 5 average rating, 73 reviews
Top guest favourite
Cottage in East Haddam
Historic Hearthstone Cottage
1 bedroom, 3 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 107 reviews