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Search results; Over 1,000 homes in Chester
Over 1,000 homes in Chester
Top guest favourite
Guest favourite
Cabin in Chester
The Farmstead Cabin
1 bedroom
1 bedroom
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
15–20 Nov
15–20 Nov
$1,195 SGD
Show price breakdown
for 5 nights
$1,195 SGD for 5 nights
Free cancellation
4.97 out of 5 average rating, 38 reviews
4.97 (38)
Guest favourite
Guest favourite
Home in Chester
Cozy Retreat for Adventurers, Artists, & Families
2 bedrooms
2 bedrooms
,
·
5 beds
5 beds
,
·
1 bathroom
1 bathroom
28 Sept – 3 Oct
28 Sept – 3 Oct
$1,483 SGD
Show price breakdown
for 5 nights
$1,483 SGD for 5 nights
Free cancellation
4.92 out of 5 average rating, 13 reviews
4.92 (13)
Home in Middlefield
Cozy Berkshires home with brook & sugar house
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
15–20 Sept
15–20 Sept
$1,319 SGD
Show price breakdown
for 5 nights
$1,319 SGD for 5 nights
New place to stay
New
Top guest favourite
Guest favourite
Home in Becket
Forest Home with Sauna
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
3.5 bathrooms
3.5 bathrooms
13–18 Sept
13–18 Sept
$2,464 SGD
$2,085 SGD
Show price breakdown
for 5 nights
4.94 out of 5 average rating, 35 reviews
4.94 (35)
Top guest favourite
Guest favourite
Farm stay in Worthington
Like sleeping on a cloud
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
3 bathrooms
3 bathrooms
9–14 Nov
9–14 Nov
$1,521 SGD
Show price breakdown
for 5 nights
$1,521 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 61 reviews
4.98 (61)
Guest favourite
Guest favourite
Home in Becket
Pristine Home In Becket Woods
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
14–19 Sept
14–19 Sept
$1,974 SGD
$1,767 SGD
Show price breakdown
for 5 nights
4.91 out of 5 average rating, 46 reviews
4.91 (46)
Guest favourite
Guest favourite
Cabin in Becket
Tranquil Lake cabin with Kayaks
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
17–22 Sept
17–22 Sept
$1,447 SGD
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for 5 nights
$1,447 SGD for 5 nights
4.86 out of 5 average rating, 42 reviews
4.86 (42)
Guest favourite
Guest favourite
Home in Otis
Family Berkshires Cabin w/ Climbing Wall, Games
4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
,
·
3 bathrooms
3 bathrooms
25–30 Sept
25–30 Sept
$2,631 SGD
Show price breakdown
for 5 nights
$2,631 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 13 reviews
5.0 (13)
Guest favourite
Guest favourite
Home in Worthington
Berkshires Carriage House - Artist's Loft, Retreat
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
26–31 Oct
26–31 Oct
$1,504 SGD
Show price breakdown
for 5 nights
$1,504 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 45 reviews
4.98 (45)
Guest favourite
Guest favourite
Home in Becket
Real Estate:Therapy - Lake, Laundry, Love it
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
28 Oct – 2 Nov
28 Oct – 2 Nov
$1,020 SGD
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for 5 nights
$1,020 SGD for 5 nights
4.88 out of 5 average rating, 378 reviews
4.88 (378)
Superhost
Superhost
Cabin in Sandisfield
The Lucas Cabin
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
24–29 Sept
24–29 Sept
$1,583 SGD
$1,267 SGD
Show price breakdown
for 5 nights
Free cancellation
New place to stay
New
Top guest favourite
Guest favourite
Home in Otis
The Berkshires Fall/Ski House - Stunning sunrise!
4 bedrooms
4 bedrooms
,
·
10 beds
10 beds
,
·
4.5 bathrooms
4.5 bathrooms
14–19 Sept
14–19 Sept
$10,412 SGD
$8,273 SGD
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for 5 nights
5.0 out of 5 average rating, 24 reviews
5.0 (24)
Guest favourite
Guest favourite
Home in Becket
Berkshires Lakefront Stylish Retreat w/Gameroom
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
14–19 Sept
14–19 Sept
$3,721 SGD
$2,882 SGD
Show price breakdown
for 5 nights
4.98 out of 5 average rating, 47 reviews
4.98 (47)
Top guest favourite
Guest favourite
Guest house in Cummington
Cozy Hilltown Cottage
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
5–10 Oct
5–10 Oct
$1,476 SGD
Show price breakdown
for 5 nights
$1,476 SGD for 5 nights
Free cancellation
4.99 out of 5 average rating, 222 reviews
4.99 (222)
Home in Chester
The Cottage at Quill Hollow
3 bedrooms
3 bedrooms
,
·
6 beds
6 beds
,
·
2 bathrooms
2 bathrooms
22–27 Sept
22–27 Sept
$2,036 SGD
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for 5 nights
$2,036 SGD for 5 nights
Guest favourite
Guest favourite
Home in Worthington
Chateau Worthington - Luxury Retreat w/ Indoor Pool
6 bedrooms
6 bedrooms
,
·
17 beds
17 beds
,
·
6.5 bathrooms
6.5 bathrooms
13–18 Sept
13–18 Sept
$12,777 SGD
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for 5 nights
$12,777 SGD for 5 nights
5.0 out of 5 average rating, 23 reviews
5.0 (23)
Top guest favourite
Guest favourite
Home in Otis
Newly rebuilt waterfront house on Otis Reservoir
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
,
·
2.5 bathrooms
2.5 bathrooms
18–23 Oct
18–23 Oct
$2,763 SGD
Show price breakdown
for 5 nights
$2,763 SGD for 5 nights
Free cancellation
4.82 out of 5 average rating, 82 reviews
4.82 (82)
Home in Worthington
Private Berkshire Chalet in Worthington
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
20–25 Sept
20–25 Sept
$2,249 SGD
$2,025 SGD
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for 5 nights
5.0 out of 5 average rating, 4 reviews
5.0 (4)
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