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Viewed 20 times in the last 48 hours
Premier Partner
  • 3 BR
  • 1 BA
Excellent! 4.7/5
(27 reviews)
avg/night
Barn #346642vb
27
  • 1 BR
  • 1 BA
avg/night
Bed And Breakfast #4621555
Viewed 16 times in the last 48 hours
  • 1 BR
  • 1 BA
  • 700 sq. ft.
Wonderful! 4.9/5
(38 reviews)
avg/night
Cottage #4018430
38
Viewed 66 times in the last 48 hours
Premier Partner
  • 4 BR
  • 3 BA
  • 1 HF BA
  • 2500 sq. ft.
Wonderful! 4.9/5
(17 reviews)
avg/night
House #1020471vb
17
Viewed 56 times in the last 48 hours
  • 5 BR
  • 5 BA
  • 2388 sq. ft.
Wonderful! 4.9/5
(43 reviews)
avg/night
House #729783vb
43
Viewed 30 times in the last 48 hours
  • 2 BR
  • 2 BA
  • 1250 sq. ft.
Wonderful! 4.9/5
(34 reviews)
avg/night
Condo #651723vb
34
Viewed 103 times in the last 48 hours
  • 3 BR
  • 2 BA
  • 1650 sq. ft.
Wonderful! 4.8/5
(20 reviews)
avg/night
House #3792910
20
Viewed 26 times in the last 48 hours
Premier Partner
  • 7 BR
  • 2 BA
  • 1 HF BA
  • 3800 sq. ft.
Exceptional! 5/5
(25 reviews)
avg/night
House #453487vb
25
Viewed 24 times in the last 48 hours
  • 3 BR
  • 1 BA
  • 1 HF BA
  • 1400 sq. ft.
Exceptional! 5/5
(23 reviews)
avg/night
House #3811779
23
Viewed 30 times in the last 48 hours
  • 3 BR
  • 2 BA
  • 2000 sq. ft.
Excellent! 4.6/5
(5 reviews)
avg/night
House #606667vb
5
Viewed 30 times in the last 48 hours
  • 4 BR
  • 2 BA
  • 1 HF BA
  • 2300 sq. ft.
Wonderful! 4.9/5
(14 reviews)
avg/night
Farmhouse #627684vb
14
Viewed 32 times in the last 48 hours
  • 2 BR
  • 1 BA
  • 625 sq. ft.
Excellent! 4.4/5
(19 reviews)
$94
avg/night
Apartment #293804
19
Viewed 33 times in the last 48 hours
  • 6 BR
  • 2 BA
  • 1 HF BA
  • 4300 sq. ft.
Exceptional! 5/5
(8 reviews)
avg/night
House #4589963
8
Viewed 37 times in the last 48 hours
  • 1 BR
  • 1 BA
Excellent! 4.7/5
(25 reviews)
avg/night
Apartment #437137vb
25
Viewed 32 times in the last 48 hours
Premier Partner
  • 3 BR
  • 1 BA
  • 1 HF BA
  • 1150 sq. ft.
Excellent! 4.7/5
(49 reviews)
avg/night
House #332468
49
Viewed 12 times in the last 48 hours
Premier Partner
  • 2 BR
  • 2 BA
  • 900 sq. ft.
Wonderful! 4.8/5
(6 reviews)
avg/night
Condo #4230132
6
Viewed 90 times in the last 48 hours
  • 7 BR
  • 3 BA
  • 1 HF BA
Wonderful! 4.9/5
(22 reviews)
avg/night
House #4223261
22
Viewed 24 times in the last 48 hours
  • 2 BR
  • 1 BA
  • 750 sq. ft.
Excellent! 4.7/5
(30 reviews)
avg/night
Condo #3471790
30
  • Studio
  • 1 BA
  • 440 sq. ft.
View details for price
Hotel #3905417
Viewed 204 times in the last 48 hours
Premier Partner
  • 6 BR
  • 5 BA
  • 7000 sq. ft.
Wonderful! 4.9/5
(48 reviews)
avg/night
Estate #4258796
48
Viewed 20 times in the last 48 hours
  • 2 BR
  • 1 BA
  • 1600 sq. ft.
Wonderful! 4.9/5
(21 reviews)
avg/night
Cottage #300900
21
Viewed 33 times in the last 48 hours
  • 5 BR
  • 3 BA
  • 2800 sq. ft.
avg/night
House #4738141
1
Viewed 99 times in the last 48 hours
  • 7 BR
  • 3 BA
  • 4002 sq. ft.
Wonderful! 4.9/5
(28 reviews)
avg/night
House #251195vb
28
Viewed 26 times in the last 48 hours
  • 2 BR
  • 1 BA
  • 1200 sq. ft.
Wonderful! 4.9/5
(7 reviews)
avg/night
Guest House #1088531vb
7
Viewed 26 times in the last 48 hours
  • 1 BR
  • 1 BA
Wonderful! 4.8/5
(32 reviews)
$90
avg/night
Cabin #189705vb
32
Viewed 31 times in the last 48 hours
  • 2 BR
  • 2 BA
  • 1250 sq. ft.
Wonderful! 4.8/5
(36 reviews)
avg/night
Condo #238631vb
36
Viewed 47 times in the last 48 hours
  • 2 BR
  • 2 BA
  • 1100 sq. ft.
Wonderful! 4.8/5
(9 reviews)
avg/night
House #190256
9
Viewed 17 times in the last 48 hours
  • 2 BR
  • 1 BA
  • 1 HF BA
  • 1500 sq. ft.
Wonderful! 4.9/5
(27 reviews)
avg/night
House #381805vb
27
  • 1 BR
  • 1 BA
  • 1 HF BA
  • 1244 sq. ft.
Exceptional! 5/5
(26 reviews)
avg/night
Cottage #486902vb
26
Viewed 13 times in the last 48 hours
  • 4 BR
  • 2 BA
  • 2540 sq. ft.
Excellent! 4.7/5
(6 reviews)
avg/night
House #4471204
6
Viewed 21 times in the last 48 hours
  • 3 BR
  • 2 BA
  • 1 HF BA
Wonderful! 4.8/5
(13 reviews)
avg/night
Condo #595232vb
13
Viewed 29 times in the last 48 hours
  • 5 BR
  • 3 BA
  • 4000 sq. ft.
Wonderful! 4.9/5
(34 reviews)
avg/night
Farmhouse #444851vb
34
Viewed 5 times in the last 48 hours
  • 3 BR
  • 2 BA
  • 1 HF BA
  • 2000 sq. ft.
Wonderful! 4.8/5
(5 reviews)
avg/night
House #1003563vb
5
Viewed 39 times in the last 48 hours
  • 2 BR
  • 1 BA
Excellent! 4.6/5
(5 reviews)
avg/night
Cabin #1140891vb
5
Viewed 8 times in the last 48 hours
  • 2 BR
  • 1 BA
  • 1008 sq. ft.
avg/night
Cabin #4086278
3
  • 2 BR
  • 2 BA
  • 1 HF BA
  • 3000 sq. ft.
Exceptional! 5/5
(8 reviews)
avg/night
Mill #480706vb
8
Viewed 6 times in the last 48 hours
  • 2 BR
  • 1 BA
  • 1100 sq. ft.
avg/night
House #987914vb
1
Viewed 27 times in the last 48 hours
Premier Partner
  • 3 BR
  • 2 BA
  • 1250 sq. ft.
Wonderful! 4.8/5
(15 reviews)
avg/night
House #4338108
15
Viewed 31 times in the last 48 hours
  • 2 BR
  • 1 BA
  • 750 sq. ft.
Wonderful! 4.8/5
(17 reviews)
avg/night
Condo #3712818
17
Viewed 5 times in the last 48 hours
  • 3 BR
  • 1 BA
Excellent! 4.6/5
(7 reviews)
avg/night
House #1026197vb
7
Viewed 33 times in the last 48 hours
  • 4 BR
  • 2 BA
  • 2400 sq. ft.
Exceptional! 5/5
(21 reviews)
avg/night
Cabin #4148351
21
Viewed 57 times in the last 48 hours
  • 3 BR
  • 2 BA
  • 1800 sq. ft.
Wonderful! 4.9/5
(30 reviews)
avg/night
House #420727vb
30
  • 2 BR
  • 1 BA
  • 1000 sq. ft.
Wonderful! 4.8/5
(25 reviews)
avg/night
House #196466vb
25
Viewed 9 times in the last 48 hours
Premier Partner
  • 4 BR
  • 2 BA
  • 1 HF BA
  • 2248 sq. ft.
Exceptional! 5/5
(19 reviews)
avg/night
House #700267vb
19
Viewed 38 times in the last 48 hours
  • 2 BR
  • 2 BA
  • 1250 sq. ft.
Exceptional! 5/5
(21 reviews)
avg/night
House #3720156
21
Viewed 55 times in the last 48 hours
  • 3 BR
  • 1 BA
  • 1 HF BA
  • 1400 sq. ft.
Excellent! 4.7/5
(23 reviews)
avg/night
Chateau / Country House #4149878
23
Viewed 8 times in the last 48 hours
  • 2 BR
  • 1 BA
  • 1 HF BA
  • 1000 sq. ft.
Wonderful! 4.9/5
(8 reviews)
avg/night
Townhome #624863vb
8
Viewed 14 times in the last 48 hours
  • 1 BR
  • 1 BA
  • 750 sq. ft.
Wonderful! 4.8/5
(13 reviews)
avg/night
Apartment #129461vb
13
  • 1 BR
  • 1 BA
  • 850 sq. ft.
avg/night
Apartment #993635vb
3
Viewed 6 times in the last 48 hours
  • 2 BR
  • 2 BA
Wonderful! 4.9/5
(47 reviews)
avg/night
Condo #134366
47

Cheshire: Houses, Condos & More (300+)

 

Recent Cheshire Reviews

Wonderful, unique home in the Berkshires

5 of 5
My whole family of 13 met up at the Playhouse for new years. We were very grateful to have had the chance to stay at this unique and beautiful home. The home is very open and allowed for a lot of different people and a dog to cohabitate with ease. The dining room table was large enough for all of us to eat together, and the shared meals we ate at it were a highlight of our trip. Unfortunately, we were not able to use the downstairs part of the house (living room, dining area and kitchen) because the heat never rose above 47 degrees in that part of the house. The bedroom downstairs was also quite chilly and a very cold hop over to the bathroom! But the yoga studio (where some of the children slept) was very warm. Our every communication with both the owner and the property manager was friendly, helpful, and accommodating. I would imagine that this is an especially wonderful place to stay in warmer weather when tennis, swimming, and hiking are an option.
  • Submitted: Jan 02, 2018
  • Stayed: Dec 2017

Great Snowboarding trip.

5 of 5
Great property. Neat and clean. Better than the pictures. You could walk to the lifts but probably won't want to. A little far. Could use a few more wine glasses but overall great property. Would stay there again.
  • Submitted: Jan 01, 2018
  • Stayed: Dec 2017