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Search results; Over 1,000 homes in Cheshire

Superhost

Home in Cheshire

19th c. Barn in The Berkshires

3 bedrooms, 6 beds, 2 private bathrooms

12–17 Jul

$3,012 SGD for 5 nights

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4.86 out of 5 average rating, 226 reviews

Townhouse in Cheshire

4 Bedrooms first floor home.

4 bedrooms, 4 beds

8–13 Jul

$1,909 SGD for 5 nights

5.0 out of 5 average rating, 4 reviews

Guest favourite

Place to stay in Cheshire

#1 Large room and bathroom in beautiful old house

1 bedroom, 1 queen bed

1–6 Sept

$1,335 SGD for 5 nights

5.0 out of 5 average rating, 6 reviews

Guest suite in Cheshire

Respite in the 'Shire

1 bedroom, 2 beds

13–18 Jul

Extended stay discount

New place to stay

Guest favourite

Cabin in Cheshire

Private Paradise in the Berkshires

1 bedroom, 1 bed

9–14 Jul

$1,327 SGD for 5 nights

4.9 out of 5 average rating, 174 reviews

Guest favourite

Flat in Adams

Downtown Studio in Adams

1 bed

2–7 Aug

$754 SGD for 5 nights

4.87 out of 5 average rating, 75 reviews

Top guest favourite

Home in Cheshire

Berkshires Lakefront Retreat by Evergreen Home

4 bedrooms, 4 beds

21–26 Jul

4.96 out of 5 average rating, 55 reviews

Guest favourite

Guest suite in Lanesborough

1bed rm. skier’s bliss 2 miles only 1 rd to slopes

1 bedroom, 2 beds

19–24 Jul

$809 SGD for 5 nights

4.81 out of 5 average rating, 93 reviews

Guest favourite

Townhouse in Hancock

Jiminy Peak Slopeside Getaway • Ski & Adventure

2 bedrooms, 3 beds

12–17 Jul

5.0 out of 5 average rating, 11 reviews

Top guest favourite

Home in Savoy

Bear Minimum

2 bedrooms, 2 queen beds

8–13 Jul

$1,792 SGD for 5 nights

4.94 out of 5 average rating, 85 reviews

Top guest favourite

Home in Lanesborough

The Pond House

3 bedrooms, 4 beds

9–14 Dec

$1,879 SGD for 5 nights

4.96 out of 5 average rating, 50 reviews

Guest favourite

Cottage in Lanesborough

Wildlife Lakeside Cottage; views/wildlife

3 bedrooms, 4 beds

9–14 Aug

$2,555 SGD for 5 nights

4.85 out of 5 average rating, 296 reviews

Guest favourite

Home in Cheshire

Cheshire Cove | Waterfront • Kayak • Firepit

2 bedrooms, 2 beds

17–22 Aug

$3,732 SGD for 5 nights

4.82 out of 5 average rating, 22 reviews

Guest favourite

Guest suite in Hancock

Cozy apartment near Jiminy Peak

2 bedrooms, 3 beds

25–30 Jul

$707 SGD for 5 nights

4.82 out of 5 average rating, 207 reviews

Home in Lanesborough

Casa Demeo, Private Berkshire Retreat

3 bedrooms, 3 beds

27 Jul – 1 Aug

$2,402 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

Guest favourite

Home in Pittsfield

Cantabile life in the Berkshires

3 bedrooms, 5 beds

23–28 Aug

$1,972 SGD for 5 nights

4.95 out of 5 average rating, 217 reviews

Guest favourite

Cabin in Windsor

Stone cabin in the Berkshires

2 bedrooms, 3 beds

3–8 Aug

$1,739 SGD for 5 nights

4.88 out of 5 average rating, 24 reviews

Guest favourite

Resort in Hancock

Country Inn Suite at Jiminy Peak - No fees added

1 bedroom, 2 beds

9–14 Jul

4.72 out of 5 average rating, 266 reviews

Guest favourite

Cabin in Hinsdale

Relaxing Berkshire cabin on Lake Ashmere

2 bedrooms, 3 beds

8–13 Jul

$2,364 SGD for 5 nights

4.96 out of 5 average rating, 46 reviews