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Search results; Over 1,000 homes in Chester

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Top guest favourite
Flat in Chester
Charming Chester Retreat - Cottage
2 bedrooms, 2 beds, 1 shared bathroom
4–9 Oct
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4.99 out of 5 average rating, 204 reviews
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Home in Chester
Chester Gingerbread House: Stroll to Village
3 bedrooms, 3 beds, 2.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 47 reviews
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Home in Chester
Historic 1836 Toll House on Brook – Walk to Town
2 bedrooms, 3 beds, 1.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 4 reviews
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Guest favourite
Flat in Chester
Chester Village 'Pied-à-terre' above art gallery
1 bedroom, 3 beds, 1 bathroom
21–26 Sept
4.91 out of 5 average rating, 435 reviews
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Cottage in Chester
Updated cottage "Beriozka" on Cedar Lake
2 bedrooms, 3 beds, 1 bathroom
19–24 Oct
4.97 out of 5 average rating, 313 reviews
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Room in Chester
Comfy Artist View at Chester Village
1 king bed, 1 bathroom
25–30 Sept
4.96 out of 5 average rating, 198 reviews
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Top guest favourite
Flat in Chester
The Little Chestnut: Walk to downtown Chester.
2 bedrooms, 3 beds, 1 bathroom
25–30 Oct
4.97 out of 5 average rating, 76 reviews
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Loft in Chester
The Village Loft: UNIQUE 1 BDRM W/ PRIVATE DECK
1 bedroom, 2 beds, 1 bathroom
28 Sept – 3 Oct
4.98 out of 5 average rating, 193 reviews
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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, 54 reviews
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Flat in Chester
The Millhouse Downtown Chester
2 bedrooms, 2 queen beds, 1.5 bathrooms
25–30 Sept
4.99 out of 5 average rating, 123 reviews
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Guest favourite
Flat in Deep River
Lovely Garden-Level Apartment in Heart of Town
2 bedrooms, 2 beds, 1 bathroom
25–30 Oct
4.93 out of 5 average rating, 176 reviews
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Room in Deep River
Riverwind Hearts & Flowers Room in Deep River
1 queen bed, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 41 reviews
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Guest favourite
Home in Chester
Charmingly Chester on the Great Brook and Pond
4 bedrooms, 4 double beds, 2.5 bathrooms
18–23 Sept
4.83 out of 5 average rating, 76 reviews
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Guest favourite
Home in Haddam
Charming 1806 farm house close to the CT River.
5 bedrooms, 7 beds, 2 bathrooms
20–25 Sept
4.93 out of 5 average rating, 161 reviews
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Guest favourite
Flat in Essex
Historic 2 BR, quick walk to downtown Essex!
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 6 reviews
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Guest favourite
Home in East Haddam
East Haddam Village | Walkable, Pet Friendly
4 bedrooms, 4 beds, 1.5 bathrooms
20–25 Sept
4.9 out of 5 average rating, 60 reviews
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Room in Ivoryton
Charming cozy room in our historic home
1 queen bed, WC
19–24 Sept
4.95 out of 5 average rating, 62 reviews
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Top guest favourite
Cottage in East Haddam
Historic Hearthstone Cottage
1 bedroom, 3 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 114 reviews
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Guest favourite
Home in East Haddam
Historic House by the River
3 bedrooms, 4 beds, 1.5 bathrooms
10–15 Oct
4.91 out of 5 average rating, 77 reviews