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Compare 826 Vacation Homes in Chester with updated reviews, rates, and availability.

Beautiful, private log cabin with huge, relaxing screened porch
10.0 out of 10, Exceptional, (24)
"The house was very comfortable for our family. It was well-stocked with plates, pots, and pans. Bed were comfortable."
Beautiful, private log cabin with huge, relaxing screened porch
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
10.0 out of 10, Exceptional, (183)
"The barn was spacious and had everything we needed. The property is breathtaking, great location to the town, and Jeff was a great host. Our dogs were welcome, living their best life running around the property, and it was so special to see the mountains and just breathe in the air there. Would love to come back in the warmer weather!"
The price is $476
$787 total
includes taxes & fees
May 20 - May 21
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
Luxurious, Secluded, Ski Chalet, w/ Country Decor & Hot Tub Near Okemo
10.0 out of 10, Exceptional, (139)
"The property was excellent and nothing beats the hot tub while it’s snowing!"
Luxurious, Secluded, Ski Chalet, w/ Country Decor & Hot Tub Near Okemo
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Private Family Estate for any Season
10.0 out of 10, Exceptional, (57)
"Beautiful place and great location."
Private Family Estate for any Season
Bright, Downtown 4-BR Home 3-min to Okemo
10.0 out of 10, Exceptional, (8)
"This rental was amazing! The house was beautiful and if this listing is available during the ski season, I will book this residence. We were comfortable and slept well here. My dogs came since we did come to the area for the solar eclipse. There is enough sidewalk and side streets to walk the dogs. I especially liked the fact all of the flooring in the house is a solid surface (no carpet) There is a general store called Singleton's, and we found lots of good food to purchase."
Bright, Downtown 4-BR Home 3-min to Okemo
Contemporary Mountain Home near Okemo, Stratton, Magic Mountain and Bromley
10.0 out of 10, Exceptional, (2)
"My family of five stayed at the house for a weekend so that we could go skiing. The house was clean, it had every cooking utensil I needed, the sleeping arrangements were perfect, and it had a nice big table for playing games. Those are our priorities. Other nice points are that the bathrooms were nice and there is a washer and dryer in the mud room - great for drying wet ski clothes. The house was about 30 minutes from Okemo mountain. We got two feet of snow the day we got there (yay!) and the...
The price is $135
$403 total
includes taxes & fees
May 6 - May 7
Contemporary Mountain Home near Okemo, Stratton, Magic Mountain and Bromley
Home base at Mount Snow
10.0 out of 10, Exceptional, (5)
"Nice well maintained 70s style house, great location , highly recommend."
Home base at Mount Snow
Relaxing Mountain Refuge: 4 Miles to Mt Snow!
10.0 out of 10, Exceptional, (6)
"This unit was so clean and well cared for. We felt right at home! And so close to both Mt Snow and all of the restaurants in Wilmington. We really enjoyed our stay and plan to return again."
Relaxing Mountain Refuge: 4 Miles to Mt Snow!
Perfect Reunion House w/fireplace & piano. Dogs welcome. Discounted ski tix at Bromley. Add private indoor pool on request.
9.8 out of 10, Exceptional, (22)
"Friendly host, ans check in process was very simple. House was big enough for 8 adults and 6 children. Location is 30-40 mins away from stratton, which we decided to go fo skiing. It felt a little further away due to traffic and busy long weekend."
Perfect Reunion House w/fireplace & piano. Dogs welcome. Discounted ski tix at Bromley. Add private indoor pool on request.
BruinsDen - Ski On Ski Off (Home Stretch Trail)
9.8 out of 10, Exceptional, (7)
"We loved our stay. There were plenty of beds and bathrooms for our family. The kitchen was the most well stocked kitchen ever. Better than being at home even! Really loved the porch area for storing ski gear. The hot tub felt great. Loved all the windows. So much light and great view. The only small draw back was it’s not a true ski in ski out. The trail is close but you do need to walk a bit to get to it. Overall we had a great visit and would stay here again!"
BruinsDen - Ski On Ski Off (Home Stretch Trail)
Storybook Stratton House: 3 Mi to Mount Snow!
9.8 out of 10, Exceptional, (7)
"Overall the house was great. Exactly as advertised"
Storybook Stratton House: 3 Mi to Mount Snow!
Riverfront, family fun, amazing rec room, close to Magic & Okemo
9.8 out of 10, Exceptional, (7)
"Very comfortable and clean home. My friends and I came into town for a snowboarding trip, and the home was the perfect fit for us."
Riverfront, family fun, amazing rec room, close to Magic & Okemo
West Dover Home w/ Deck, Grill & EV Outlet
9.8 out of 10, Exceptional, (16)
"Long weekend ski trip to Mt. Snow with three families. Layout of bedrooms and living spaces was perfect. Location to Mt. Snow and area market and restaurants was also perfect. We’ll be back."
West Dover Home w/ Deck, Grill & EV Outlet
Summer Deals Free Gym Pool Pass- Luxury Log Home, 6 BR/4BA, Pool Table, Hot Tub
9.8 out of 10, Exceptional, (156)
"Communication with owners was amazing. Heather was a great respondent and communicator. We were able to get three generations under one roof for a quiet and relaxing family getaway. We shared old stories around the fireplace and played cards late into the night (which is ten thirty pm, for us). Both my father and sister commented, at separate times, that the location was relaxing and peaceful. The pictures represent the property correctly. This was my first experience with VRBO and I am...
Summer Deals Free Gym Pool Pass- Luxury Log Home, 6 BR/4BA, Pool Table, Hot Tub
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
9.8 out of 10, Exceptional, (107)
"Clean home close to downtown. Responsive owner. Highly recommended"
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
9.8 out of 10, Exceptional, (187)
"We had a lovely stay, the kayaks and canoe were the feature of one afternoon and we greatly enjoyed paddling around Lake Pauline and checking out both dam areas. The house is very clean and well maintained, we fell in love with all the windows and light coming in the bedroom across from the bathroom. The quick walk to the sugar house was a feature for my kids, they also loved having the wii in their room and playing Mario kart with their aunt/uncle."
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
9.6 out of 10, Exceptional, (29)
"Two families stayed for a ski trip to okemo. Proximity to the mountain was a big plus for us. The cabin is cozy."
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Private home with fireplace, grill, games, AC & great Manchester location
9.6 out of 10, Exceptional, (5)
"Probably one of the best rentals I've been to. Clean, nicely renovated, a short drive to Manchester center. "
Private home with fireplace, grill, games, AC & great Manchester location
Hike, Explore, Swim ~ Adventure in Vermont!
9.6 out of 10, Exceptional, (40)
"The owner had the place ready to go when we arrived. It was a late arrival, but there were outside lights that were warm and inviting. Plenty of space for our party of 12 (6 adults and 6 kids). Kitchen was welled stocked with cooking necessities, great hangout spaces in the basement and first floor, and a convenient space for ski boots and outer gear in the basement near parking. Kids absolutely loved the pool - and have the pruned hands to prove it. The location couldn't have been better, ~25...
Hike, Explore, Swim ~ Adventure in Vermont!
Charming Chester Farmhouse – peaceful and close to everything!
9.6 out of 10, Exceptional, (5)
"The farmhouse was clean, comfortable and convenient. Just what we were looking for. Our host was very helpful and pleasant. We would be happy to stay here again."
The price is $190
$391 total
includes taxes & fees
May 12 - May 13
Charming Chester Farmhouse – peaceful and close to everything!
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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.

Other property types in Chester

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
9.6 out of 10, Exceptional, (29)
"Two families stayed for a ski trip to okemo. Proximity to the mountain was a big plus for us. The cabin is cozy."
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
9.6 out of 10, Exceptional, (176)
"Third time as good as the first. We will return next year"
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
9.4 out of 10, Exceptional, (47)
"We loved our stay at the chalet. It's perfectly situated in the cutest little neighborhood, while also feeling very secluded. The chalet had everything we needed for our stay. While visiting we walked a few of the trails nearby, part of the Valley Trail and the Hoot, Toot and Whistle. They were both perfect for our pups, especially during hunting season. We gave our pups an extra squeeze in honor of Scarlet. Thank you for sharing your place with us! We would love to stay again!!"
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
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.

Chester Vacation Homes information

Number of reviews
874
Accommodation
826 Vacation Homes
Lowest Price
$135
Highest Price
$476

Recent reviews of Chester hotels
Expedia verified reviews