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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
28 Sept – 3 Oct
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4.98 out of 5 average rating, 190 reviews
Top guest favourite
Home in Chester
Chester Gingerbread House: Stroll to Village
3 bedrooms, 3 beds
4–9 Oct
5.0 out of 5 average rating, 47 reviews
Guest favourite
Flat in Chester
Chester Village 'Pied-à-terre' above art gallery
1 bedroom, 3 beds
13–18 Sept
4.91 out of 5 average rating, 434 reviews
Home in Chester
Historic 1836 Toll House on Brook – Walk to Town
2 bedrooms, 3 beds
13–18 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Flat in Chester
The Little Chestnut: Walk to downtown Chester.
2 bedrooms, 3 beds
11–16 Oct
4.97 out of 5 average rating, 74 reviews
Top guest favourite
Cottage in Chester
Updated cottage "Beriozka" on Cedar Lake
2 bedrooms, 3 beds
19–24 Oct
4.97 out of 5 average rating, 313 reviews
Top guest favourite
Room in Chester
Comfy Artist View at Chester Village
1 king bed
18–23 Sept
4.96 out of 5 average rating, 198 reviews
Top guest favourite
Flat in Chester
Charming Chester Retreat - Cottage
2 bedrooms, 2 queen beds
4–9 Oct
4.99 out of 5 average rating, 203 reviews
Top guest favourite
Guest suite in Essex
The Nest
1 bedroom, 1 bed
10–15 Nov
4.97 out of 5 average rating, 135 reviews
Guest favourite
Home in Essex
Bushy Hill House
3 bedrooms, 4 beds
16–21 Sept
5.0 out of 5 average rating, 6 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, 54 reviews
Top guest favourite
Flat in Deep River
Lovely Garden-Level Apartment in Heart of Town
2 bedrooms, 2 beds
25–30 Oct
4.94 out of 5 average rating, 174 reviews
Top guest favourite
Room in Deep River
Riverwind Hearts & Flowers Room in Deep River
1 queen bed
14–19 Sept
4.98 out of 5 average rating, 40 reviews
Guest favourite
Flat in Essex
Historic 2 BR, quick walk to downtown Essex!
2 bedrooms, 2 beds
16–21 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Flat in Chester
The Millhouse Downtown Chester
2 bedrooms, 2 queen beds
13–18 Sept
4.99 out of 5 average rating, 123 reviews
Guest favourite
Guest house in Clinton
Clinton's Secret, Beach Pass, Pet Friendly
2 bedrooms, 2 beds
10–15 Sept
4.97 out of 5 average rating, 29 reviews
Top guest favourite
Home in Essex
Ideal Historic Home in Essex Village
2 bedrooms, 3 beds
9–14 Nov
4.97 out of 5 average rating, 99 reviews
Guest favourite
Home in Haddam
Quarry House: Mid-Century Modern
4 bedrooms, 5 beds
9–14 Sept
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Home in Clinton
The Connecticut Cottage | Historic Modern Charm
2 bedrooms, 2 beds
20–25 Sept
4.97 out of 5 average rating, 29 reviews