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Compare 890 Vacation Homes in Chester with updated reviews, rates, and availability.

Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!

10.0 out of 10, Exceptional, (40)
"the condo is fully equipped for anything and everything. the location could not be better and the host was extremely responsive. we will be back for sure!thanks!"
The price is SAR 1,099
SAR 2,238 total
includes taxes & fees
27 Jan - 28 Jan
Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!

Secluded, rustic home w/ private hot tub & immense nature - 5 miles to Stratton

9.8 out of 10, Exceptional, (30)
"One of the best experiences I’ve had. Communication before we arrived was as expected, and everything was better than the pictures reviews and descriptions."
The price is SAR 2,060
SAR 4,968 total
includes taxes & fees
2 Feb - 3 Feb
Secluded, rustic home w/ private hot tub & immense nature - 5 miles to Stratton

Beautiful! 5 Beds-5 baths Home, Spectacular Views of Stratton, On Shuttle

10.0 out of 10, Exceptional, (35)
"The house is beautiful and everything on the description was accurate. Had a great stay. "
Beautiful! 5 Beds-5 baths Home, Spectacular Views of Stratton, On Shuttle

Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

9.8 out of 10, Exceptional, (201)
"My family and I just returned from our New Years stay at “Cozy Cottage”. The home is beautifully appointed and equipped with everything you could possibly need. Waking up every morning in the sun room overlooking the lake was an absolute dream especially on a snowy day. The location is fantastic, as it’s a stones throw to Okemo, and about a 7 min drive to the town of Ludlow where you will find a grocery store, quaint shops, and dining. We definitely plan to return!"
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

Spacious Townhome with breathtaking views of Mount Snow. 5 min Shuttle to ski

10.0 out of 10, Exceptional, (19)
"We had a wonderful stay! Perfect condo for two families. The two living room areas were nice so the kids could watch a movie downstairs while the adults hung out upstairs. The ease to Mount Snow is unbeatable with the Moover shuttle pickup and drop off right out the front door. And access to the community center after a full day skiing was a great benefit. We highly recommend this property and will definitely return! "
Spacious Townhome with breathtaking views of Mount Snow. 5 min Shuttle to ski

Ski-In condo at Mount Snow with Fireplace, Bears Crossing

10.0 out of 10, Exceptional, (12)
"Wonderful time. The place was great just as advertised. Easy to get to slopes via moover shuttle. We were 6 adults and all enjoyed the space. Only surprise was bathrooms were on bottom floor. But no big deal. Thanks Nancy! We hope to make this an annual weekend. "
Ski-In condo at Mount Snow with Fireplace, Bears Crossing

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

10.0 out of 10, Exceptional, (1)
"We had an absolute amazing stay at Todd‘s place. Communication was extremely responsive. This was a last-minute trip with the family during the holiday and we had an absolute blast. The kids had so much fun in the bunk bedroom. The house is extremely spacious and absolutely beautiful. To be able to ski to the backyard was such a luxury. This was a special house with an unreal location. We will be coming back in February. Thank you so much for the memories."
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

9.8 out of 10, Exceptional, (19)
"Great Location! Very short drive to Skyeship Gondola. Property was well equipped for all our needs."
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

9.8 out of 10, Exceptional, (89)
"Everything about this property was perfect for our family of 6! Location, charm and cleanliness, perfection! "
The price is SAR 960
SAR 1,815 total
includes taxes & fees
4 Feb - 5 Feb
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Historic 6-BR Across From Equinox Resort

9.0 out of 10, Wonderful, (7)
"Wonderful spot for a family holiday gathering! Had some plumbing issues but property manager was very responsive and did the very best he could to remedy. A helpful note if your party includes those who can’t do stairs - there are no bedrooms on the main floor. Given the age and charm of the house, the stairs to the basement and 2nd floor could be a challenge for older folks. Would definitely return!"
Historic 6-BR Across From Equinox Resort

BruinsDen - Ski On Ski Off (Home Stretch Trail)

10.0 out of 10, Exceptional, (11)
"Wonderful home! Excellent layout for family bonding. Hot tub was great. Skiing equipment storage area was Lu fantastic. Easy ski-in ski-out!!! Communication with host was excellent!! Beds were comfy! Would highly recommend! "
The price is SAR 2,147
SAR 4,113 total
includes taxes & fees
27 Jan - 28 Jan
BruinsDen - Ski On Ski Off (Home Stretch Trail)

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

10.0 out of 10, Exceptional, (12)
"My family enjoyed our stay at this house. It had plenty of room for all of us and the 5 bathrooms were great to have. Extremely clean. We didnt use the hot tub because it was too cold but that is definitely a plus to have. It is only a few minutes from Manchester Center and close to a lot of other restaurants and shops. The ownwr reached out days in advance and was available if needed, which we didnt. We will definitely be looking to book this house in the future! A++++"
The price is SAR 1,705
SAR 3,584 total
includes taxes & fees
23 Jan - 24 Jan
Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Modern Farm House…minutes to Okemo; 2 King beds!

9.4 out of 10, Exceptional, (9)
"It is the perfect house for two families to stay in for a ski weekend. There are plenty of arcade and board games to entertain the teens. We will be back!"
Modern Farm House…minutes to Okemo; 2 King beds!

Secluded Rustic Home with Private Hot Tub & Huge Deck - 5 Miles to Okemo

9.8 out of 10, Exceptional, (38)
"The property is recently renovated so everything is relatively new and in good condition. The unique design choice of using cedar for the walls, floors and ceiling was a bit off putting initially but we got used to it. There was a small issue with the hot tub, but the host responded very quickly and the issue was resolved the next day. Will definitely consider staying here for the next Okemo ski vacation."
Secluded Rustic Home with Private Hot Tub & Huge Deck - 5 Miles to Okemo

Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River

10.0 out of 10, Exceptional, (7)
"My wife, our dog, and I had a terrific stay at the Sugar River Treehouse- we were in town for a few days to ski and spend New Years here, and couldn't have asked for a cozier place to stay in the woods of NH nearby a river! The outside area produced perfect morning & evening walks with the pup, and the new house with updated features (our favorite was the heated bathroom floors) was located very close to town with restaurants and amenities. We would happily stay here again!"
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River

Vermont's Mountain Villa: Hot tub, Ski views, Pet+

10.0 out of 10, Exceptional, (7)
"My partner and I booked this property for a long weekend in December as a romantic getaway. This place was perfect for what we were looking for to escape the city. The house was a bit up the mountain, which was ideal as we wanted a bit of privacy and to enjoy nature. The kitchen was stocked with all the things we needed, including sharp knives! The beds were comfortable and the double-sided fireplace was fantastic, plus there was plenty of firewood in the garage. It was clean and bright, quite...
Vermont's Mountain Villa: Hot tub, Ski views, Pet+

Cozy Vermont House Near Killington and Woodstock. Discounted lift tickets!

Cozy Vermont House Near Killington and Woodstock. Discounted lift tickets!

Skiers townhouse close to Stratton w/ balcony, mudroom, w/d, wifi, kitchen

Skiers townhouse close to Stratton w/ balcony, mudroom, w/d, wifi, kitchen

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

9.6 out of 10, Exceptional, (35)
"Convenient to Okemo. Has everything you need for a ski week or weekend! "
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.

10.0 out of 10, Exceptional, (39)
"This property was beautiful, clean, well maintained, had everything we needed. Wish we could have stayed longer! Thank you for a weekend we’ll never forget! We hope to rent this house again in the future. "
Secluded Escape in Rural Vermont! Sauna Pool, Hot Tub,Game House Mountain Views.
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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Other property types in Chester

Long Trail House at Stratton Mountain Resort

3.0 star property
8.4 out of 10, Very Good, (72)
"Condo was great, cozy, and clean. Has access to the pool and hot tubs from back porch and has great Mountain View’s. The village had plenty of food, little expensive, but pretty good. Overall great place to stay and enjoy the mountain. "
The price is SAR 1,467
SAR 1,823 total
includes taxes & fees
28 Jan - 29 Jan
Long Trail House at Stratton Mountain Resort

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

9.6 out of 10, Exceptional, (35)
"Convenient to Okemo. Has everything you need for a ski week or weekend! "
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

9.8 out of 10, Exceptional, (165)
"The property is exactly like the pictures indicate. The house is in a friendly neighborhood outside of town. The house is very comfortable and spacious. The host responds to your messages in timely manner, and, she is very workable. Would definitely stay there again "
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
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.