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Search results; Over 1,000 homes in Chesterfield
Over 1,000 homes in Chesterfield
Photo 1 of 29
Top guest favourite
Guest favourite
Cabin in Chesterfield
Hilltown Cabin Hideaway: A River Runs Through It!
3 bedrooms
,
·
3 beds
,
·
1 private bathroom
1–6 May
1–6 May
$1,976 SGD
Show price breakdown
for 5 nights
$1,976 SGD for 5 nights
,
·
4.98 out of 5 average rating, 127 reviews
4.98 (127)
Photo 1 of 22
Top guest favourite
Guest favourite
Cabin in Chesterfield
The Glow Room at Indian Hollow
1 bedroom
1 bedroom
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
3–8 Oct
3–8 Oct
$1,966 SGD
Show price breakdown
for 5 nights
$1,966 SGD for 5 nights
4.92 out of 5 average rating, 124 reviews
4.92 (124)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Chesterfield
High Field Farm
5 bedrooms
5 bedrooms
,
·
6 beds
6 beds
,
·
2 bathrooms
2 bathrooms
1–6 May
1–6 May
$4,180 SGD
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for 5 nights
$4,180 SGD for 5 nights
Free cancellation
4.99 out of 5 average rating, 73 reviews
4.99 (73)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Cummington
Beautiful Secluded Country House
6 bedrooms
6 bedrooms
,
·
11 beds
11 beds
,
·
3 bathrooms
3 bathrooms
1–6 Oct
1–6 Oct
$3,771 SGD
$3,360 SGD
Show price breakdown
for 5 nights
4.91 out of 5 average rating, 126 reviews
4.91 (126)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Worthington
Extraordinary Berkshires Estate & Carriage House
9 bedrooms
9 bedrooms
,
·
21 beds
21 beds
,
·
7.5 bathrooms
7.5 bathrooms
26–31 Oct
26–31 Oct
$20,307 SGD
Show price breakdown
for 5 nights
$20,307 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 20 reviews
5.0 (20)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Worthington
Private Berkshire Chalet in Worthington
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
11–16 Oct
11–16 Oct
$2,580 SGD
$2,307 SGD
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for 5 nights
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Photo 1 of 13
Top guest favourite
Guest favourite
Cabin in Cummington
Just Be Cabin
1 double bed
1 double bed
,
·
WC
WC
18–23 Oct
18–23 Oct
$669 SGD
$586 SGD
Show price breakdown
for 5 nights
Free cancellation
4.98 out of 5 average rating, 270 reviews
4.98 (270)
Photo 1 of 29
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
26–31 Oct
26–31 Oct
$12,870 SGD
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for 5 nights
$12,870 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 24 reviews
5.0 (24)
Photo 1 of 29
Top guest favourite
Guest favourite
Flat in Sunderland
A Cozy Condo Near Horse Farm + Mount Sugarloaf
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
4–9 Oct
4–9 Oct
$1,970 SGD
Show price breakdown
for 5 nights
$1,970 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 8 reviews
5.0 (8)
Photo 1 of 29
Guest favourite
Guest favourite
Campsite in Chesterfield
Hilltown Hideaway Riverside A-Frame
1 bedroom
1 bedroom
,
·
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
19–24 Oct
19–24 Oct
$1,451 SGD
$1,180 SGD
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for 5 nights
4.96 out of 5 average rating, 52 reviews
4.96 (52)
Photo 1 of 29
Top guest favourite
Guest favourite
Farm stay in Williamsburg
Charming, updated , 3 bedroom farmhouse farm stay
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
11–16 Oct
11–16 Oct
$2,042 SGD
Show price breakdown
for 5 nights
$2,042 SGD for 5 nights
Free cancellation
4.99 out of 5 average rating, 156 reviews
4.99 (156)
Photo 1 of 21
Guest favourite
Guest favourite
Home in Northampton
Home in Northampton
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2.5 bathrooms
2.5 bathrooms
25–30 Oct
25–30 Oct
$2,661 SGD
$2,336 SGD
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for 5 nights
Free cancellation
4.85 out of 5 average rating, 55 reviews
4.85 (55)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Cummington
River-front home in Berkshire hills w/tennis court
4 bedrooms
4 bedrooms
,
·
6 beds
6 beds
,
·
3 bathrooms
3 bathrooms
4–9 Oct
4–9 Oct
$5,784 SGD
$5,079 SGD
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for 5 nights
5.0 out of 5 average rating, 19 reviews
5.0 (19)
Photo 1 of 19
Guest favourite
Guest favourite
Cabin in Williamsburg
Retreat in the Woods
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
1–6 Nov
1–6 Nov
$1,157 SGD
$1,023 SGD
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for 5 nights
Free cancellation
4.93 out of 5 average rating, 57 reviews
4.93 (57)
Photo 1 of 18
Top guest favourite
Guest favourite
Home in Goshen
Light-filled Lake House in Goshen
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
1–7 Oct
1–7 Oct
$2,635 SGD
$2,397 SGD
Show price breakdown
for 6 nights
5.0 out of 5 average rating, 37 reviews
5.0 (37)
Photo 1 of 12
Guest favourite
Guest favourite
Cabin in Williamsburg
Little Blue 2
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
1 bathroom
1 bathroom
4–9 Jan
4–9 Jan
$3,494 SGD
$3,067 SGD
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for 5 nights
Free cancellation
5.0 out of 5 average rating, 8 reviews
5.0 (8)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Chester
Riverhouse! Peak Foliage October 10-24
2 bedrooms
2 bedrooms
,
·
5 beds
5 beds
,
·
1 bathroom
1 bathroom
4–9 Oct
4–9 Oct
$1,373 SGD
Show price breakdown
for 5 nights
$1,373 SGD for 5 nights
Free cancellation
4.92 out of 5 average rating, 13 reviews
4.92 (13)
Photo 1 of 29
Guest favourite
Guest favourite
Villa in Whately
Valley View Post & Beam Villa
6 bedrooms
6 bedrooms
,
·
8 beds
8 beds
,
·
3.5 bathrooms
3.5 bathrooms
22–27 Oct
22–27 Oct
$13,391 SGD
$11,715 SGD
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for 5 nights
Free cancellation
4.99 out of 5 average rating, 80 reviews
4.99 (80)
Photo 1 of 29
Top guest favourite
Guest favourite
Cottage in Becket
Berkshires Cottage by Lake. Year Round Adventures.
2 bedrooms
2 bedrooms
,
·
2 double beds
2 double beds
,
·
1 bathroom
1 bathroom
18–23 Oct
18–23 Oct
$1,395 SGD
Show price breakdown
for 5 nights
$1,395 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 320 reviews
4.95 (320)
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