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Compare 910 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, (44)
"Clean, ideal location, great communication."
The price is SAR 413
SAR 1,356 total
includes taxes & fees
25 Mar - 26 Mar
Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!

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

10.0 out of 10, Exceptional, (37)
"This was a fantastic home for our family of 8 plus a toddler. The house is spacious and yet cozy, with everything one would need. The beds were very comfortable as were the sectionals on each floor. Playing games with a warm fire and expansive views…. A really special treat to stay here. And Beth is responsive and super accommodating. "
Beautiful! 5 Beds-5 baths Home, Spectacular Views of Stratton, On Shuttle

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

10.0 out of 10, Exceptional, (5)
"Everything was really nice! The house was great and the whole place lovely. Great location! The manager was really helpful and easy to get in touch with. He was able to help us with all of our questions. The conditions of the mountain were really good. Wonderful stay! "
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

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

9.8 out of 10, Exceptional, (202)
"Great place after a long day of skiing. Very close to Jackson Gore base area. The house was clean and communication was spot on. "
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

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

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

10.0 out of 10, Exceptional, (22)
"Wonderful ski vacation in this beautiful townhouse. Location is perfect. Plenty of room. Very clean and comfortable. Thank you for a great stay. "
Spacious Townhome with breathtaking views of Mount Snow. 5 min Shuttle to ski

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

9.8 out of 10, Exceptional, (19)
"The gondola house was perfect for our group. It was spacious and comfortable. Loved having a bathroom on every floor. It was well stocked with everything we could’ve needed. I don’t have one bad thing to say about it. The hot tub was just lovely after a long day of skiing. Would not hesitate to rent this again and highly recommend it."
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

10.0 out of 10, Exceptional, (14)
"Family ski weekend. Our stay was very comfortable. Communication with host was phenomenal, always prompt and courteous Location is nice , very close to the ski resorts "
The price is SAR 1,724
SAR 3,674 total
includes taxes & fees
24 Feb - 25 Feb
Your Vermont Mountain Haven Pet Friendly home with Hot tub!

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

9.8 out of 10, Exceptional, (91)
"Everything was as advertised! Great location and easy to find. "
The price is SAR 893
SAR 1,735 total
includes taxes & fees
25 Mar - 26 Mar
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

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

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

10.0 out of 10, Exceptional, (8)
"I love Winter and love to be in the snow and crisp air. The week was perfect for outside adventures and this home was perfect to warm us and nourish our hearts, bellies and spirits. The views at sunrise and sunset are extrodinary. "
Vermont's Mountain Villa: Hot tub, Ski views, Pet+

Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

8.0 out of 10, Very Good, (2)
" short stay "
Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

Historic 6-BR Across From Equinox Resort

9.0 out of 10, Wonderful, (8)
"Really enjoyed our stay"
Historic 6-BR Across From Equinox Resort

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

9.4 out of 10, Exceptional, (9)
"We were a few families visiting for a ski weekend. Location was great and the house was clean, updated, and had plenty of space. Only thing we thought was inconvenient was the lack of spare TP! "
Modern Farm House…minutes to Okemo; 2 King beds!

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

10.0 out of 10, Exceptional, (8)
"The Sugar River Treehouse is thoughtfully designed providing all the amenities needed. We thoroughly enjoyed being able to experience a unique setting with our two dogs. We plan on returning in the summer to enjoy the benefits of the Sugar River. "
Sugar River Treehouse -relaxing escape among the trees on the serene Sugar River

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 1,588
SAR 3,421 total
includes taxes & fees
3 Mar - 4 Mar
BruinsDen - Ski On Ski Off (Home Stretch Trail)

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

10.0 out of 10, Exceptional, (1)
"Beautiful house well stocked with spices and everything you need. The only thing they are missing is there’s no hairdryer and I called a few times to the property manager for a blanket because the master upstairs has no blanket and I never received one."
Skiers townhouse close to Stratton w/ balcony, mudroom, w/d, wifi, kitchen

Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.

10.0 out of 10, Exceptional, (45)
"This house was so much fun! We had a large group of families with young children and there was plenty of space for everyone. The adults were able to hang upstairs in front of the fireplace while the kids were able to play downstairs in their own space. The additional house with game room was also a ton of fun! There were so many bedrooms as well!"
Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.

New! Family Townhome with Hot Tub, Shuttle service

9.8 out of 10, Exceptional, (7)
"We stayed for 5 nights in February and had a wonderful time. The house was clean, had everything we needed and was a short ride to both the mountain and restaurants. "
New! Family Townhome with Hot Tub, Shuttle service

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

9.6 out of 10, Exceptional, (36)
"The home is as described with plenty of space for my family of 5. The kitchen was well stocked, and the bathrooms were clean. Plenty of towels and the beds were firm with clean sheets. The views of Lake Rescue were beautiful. The driveway was snow-covered, but with a 4WD, you should have no issue. The 'commute' to Okemo was easy - 8min max. The house seems to have been empty, so a musty smell permeated the home for the first day until the air circulated a few times. Not a big deal. The gas...
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
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

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

10.0 out of 10, Exceptional, (22)
"Loved being tucked away in the wilderness. Owners were very responsive. "
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

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 1,481
SAR 1,841 total
includes taxes & fees
25 Mar - 26 Mar
Long Trail House at Stratton Mountain Resort

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (41)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
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.