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Vacation Homes in Cheshire County

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Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Featured Vacation Homes in Cheshire County

Dining
FaLL Western Mass Getaway-Airhockey-Firepit

Holiday Home in Colrain

9.8 out of 10, Exceptional, (38)
"Great place and convenient to get to and from Berkshire East."
United States
Jeffrey B.
The price is HK$2,205
HK$4,985 total
includes taxes & fees
8 Dec - 9 Dec
FaLL Western Mass Getaway-Airhockey-Firepit
Interior
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews

Holiday Home in Wilmington

10.0 out of 10, Exceptional, (227)
"Spectacular view and very peaceful."
United States
Beth B.
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
Fridge, microwave, oven, stovetop
500ft across the street to Carnitha. Gromet to main lift or take Moover to Base

Holiday Home in Dover

9.8 out of 10, Exceptional, (48)
"Overall a nice stay, thanks Jen!"
United States
Anonymous traveller
500ft across the street to Carnitha. Gromet to main lift or take Moover to Base
Miscellaneous
Private Beach And Mountain Lake Home

Holiday Home in Washington

9.6 out of 10, Exceptional, (124)
"Just returned from a wonderful stay at this property. The house was clean and had everything you could need while on vacation. The pond was so clean and clear. We even saw a loon."
United States
Patricia K.
Private Beach And Mountain Lake Home
Smart TV, fireplace, DVD player, ping pong
Beautiful Custom Built Timber Frame Home, Sleeps 11

Holiday Home in Wilmington

10.0 out of 10, Exceptional, (108)
"Met family here and was a fantastic place for get together "
United States
Melissa C.
Beautiful Custom Built Timber Frame Home, Sleeps 11
Fridge, microwave, oven, stovetop
Luxury Renovated Mount Snow Chalet with Upscale Amenities– Sleeps 12!

Holiday Home in West Dover Vermont

9.6 out of 10, Exceptional, (26)
"Perfect location to walk to slopes. The host was phenomenal! Very responsive and helpful. Can’t wait to stay again soon!"
United States
R B.
Luxury Renovated Mount Snow Chalet with Upscale Amenities– Sleeps 12!
Fridge, microwave, oven, stovetop
Spacious Riverfront Home 7 Minutes to Stratton!

Holiday Home in Jamaica

10.0 out of 10, Exceptional, (36)
"Perfect house for a few families to gather and have fun. "
United States
James D.
Spacious Riverfront Home 7 Minutes to Stratton!
Interior
16 ppl 2 hot tubs, game room, fire pit

Holiday Home in Antrim

9.8 out of 10, Exceptional, (9)
"Clean, lots of space, helpful host, hot tub was also nice"
United States
Howard H.
The price is HK$1,394
HK$3,134 total
includes taxes & fees
10 Dec - 11 Dec
16 ppl 2 hot tubs, game room, fire pit
Exterior
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.

Holiday Home in Shelburne Falls

2.0 star property
10.0 out of 10, Exceptional, (20)
"Great place to stay ,close to town.Very clean."
United States
Hope D.
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.
Terrace/patio
Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC

Holiday Home in Townshend

10.0 out of 10, Exceptional, (7)
Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC
Interior
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

Holiday Home in Dover

10.0 out of 10, Exceptional, (11)
"Beautiful new home, great for big family and friend groups. Comfortable bedding and furniture. Lots of open space and seating "
United States
Gena L.
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
TV, fireplace
Beautiful dog-friendly house w/ fireplace, firepit, bbq, deck, patio, w/d, wifi

Holiday Home in Mountain Acres

9.6 out of 10, Exceptional, (4)
"We had an amazing time in Vermont and really enjoyed our stay. All of the bathrooms are updated and the home is clean and big. Rooms are separated giving privacy throughout. Thank you!!"
United States
Anonymous traveller
Beautiful dog-friendly house w/ fireplace, firepit, bbq, deck, patio, w/d, wifi
Interior
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

Holiday Home in Whitingham

10.0 out of 10, Exceptional, (50)
"Great stay perfect for 2 people, relax on then porch and look at the lake! "
United States
Keith D.
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included
Outdoor dining
Six Bedroom Mountain Estate with Internet Access

Holiday Home in West Dover

10.0 out of 10, Exceptional, (16)
"This house was great for a family gathering! It had a lot of space, has a great game room for the kids, is very clean and comfortable, and is close to Mt. Snow! It checked off all the boxes we were looking for-"
United States
Steven Z.
Six Bedroom Mountain Estate with Internet Access
Interior
Lovely 2nd Floor Apartment

Holiday Home in Greenfield

10.0 out of 10, Exceptional, (45)
"Our stay was so amazing. The hosts were wonderul and really adapatable to our family needs."
United States
Wendy M.
The price is HK$904
HK$1,575 total
includes taxes & fees
12 Dec - 13 Dec
Lovely 2nd Floor Apartment
Terrace/patio
Bears Den Chalet | Ski Home Trail, Moover Shuttle, Outdoor Hot Tub!

Holiday Home in West Dover

10.0 out of 10, Exceptional, (14)
"The house is located conveniently close to everything you need to enjoy the mountain and surrounding amenities. Perfectly laid out home to enjoy apres ski with family and friends."
United States
Robert C.
Bears Den Chalet | Ski Home Trail, Moover Shuttle, Outdoor Hot Tub!
Dining
Lakefront 3BR Log Cabin w/ Dock and Fire Pit

Holiday Home in Rindge

10.0 out of 10, Exceptional, (56)
"What a Great vacation spot and a fantastic host. Alfred was very accommodating to us and made our stay awesome. The lake was beautiful and we caught several fish and enjoyed kayaking. The fire pit was wonderful for the family at night after the long day on the lake. Thank you again Alfred for making our stay truly a memory for a life time."
United States
Jessica F.
Lakefront 3BR Log Cabin w/ Dock and Fire Pit
TV, fireplace
Pet Friendly Ski House, Game Rm, 4 Mins to Mt Snow

Holiday Home in Dover

2.0 star property
9.0 out of 10, Wonderful, (2)
"Weekend stay.Clean, comfortable, well equipped. Was as advertised.I would stay there again"
United States
Noah K.
The price is HK$2,725
HK$5,815 total
includes taxes & fees
5 Jan - 6 Jan 2026
Pet Friendly Ski House, Game Rm, 4 Mins to Mt Snow
Interior
Townhome with patio & on-site pool, hot tub, sauna & tennis access

Holiday Home in Cavendish

9.4 out of 10, Exceptional, (9)
"Had a great stay, I highly recommend "
United States
Jeffrey M.
Townhome with patio & on-site pool, hot tub, sauna & tennis access
Fridge, microwave, oven, stovetop
The Carol - 10 minutes to Okemo & Newly Renovated

Holiday Home in Cavendish

10.0 out of 10, Exceptional, (6)
"Check in and check out were incredibly easy, house decor was eclectic upscale, beds were super comfortable. Thank you Chris! Would definitely stay here again"
United States
Esther K.
The price is HK$1,282
HK$2,395 total
includes taxes & fees
8 Dec - 9 Dec
The Carol - 10 minutes to Okemo & Newly Renovated
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Cheshire County Hotel Reviews

The White House Inn

The White House Inn

10/10 Excellent
"Retro and sweet. Nice staff. No elevator. "
Christine 2-night trip
Posted 6 days ago
The White House Inn

Find out more about Cheshire County

Cheshire County Vacation Homes information

Number of reviews
802
Accommodation
628 Vacation Homes
Lowest Price
HK$1,575
Highest Price
HK$5,815