Holiday Homes in Chester

Featured Holiday Homes in Chester

TV, fireplace
Quaint mountain retreat with a gas fireplace, balcony, central AC - dog-friendly
9.2 out of 10, Wonderful, (15)
"Great location- 10-15min from Stratton, beautiful views, all the amenities. Awesome decor, will definitely be back!"
Quaint mountain retreat with a gas fireplace, balcony, central AC - dog-friendly
Fridge, microwave, oven, stovetop
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
9.6 out of 10, Exceptional, (30)
"My family really enjoyed this Lake House. The beautiful views of the lake were breathtaking. The house had everything we needed for preparing meals. The kitchen was functional and generally well equipped. The beds in the house were particularly comfortable. We enjoyed early morning coffee on the deck with perfect views of the lake. The location was great. Lots of wonderful hiking trials in close proximity. My only suggestion to the owners is to give the house a good deep cleaning. Nonetheless,...
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Property grounds
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!"
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
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Interior
Wise Pines Renovated Barn (Bunkhouse)
10.0 out of 10, Exceptional, (3)
"Thank you!"
The price is AU$657
per night
28 May - 29 May
Wise Pines Renovated Barn (Bunkhouse)
Fridge, microwave, stovetop, dishwasher
Upscale VT Getaway by Slopes, Lakes & Trails!
9.4 out of 10, Exceptional, (13)
"8 people. Good home layout for people to be together and separate at the same time"
Upscale VT Getaway by Slopes, Lakes & Trails!
Property grounds
Idyllic Lakefront House Suited Two Families
9.8 out of 10, Exceptional, (141)
"Ursula was super helpful and the location is very charming. Perfect spot for us!"
The price is AU$784
per night
1 June - 2 June
Idyllic Lakefront House Suited Two Families
Fridge, microwave, oven, stovetop
Lakefront home with amazing views, fireplace, firepit, & gas grill
9.8 out of 10, Exceptional, (58)
"Awesome house. Great location. I would stay there again for sure!"
Lakefront home with amazing views, fireplace, firepit, & gas grill
Property grounds
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
TV, fireplace, DVD player
Rustic home with a private hot tub, fireplace, cable, & washer/dryer
9.6 out of 10, Exceptional, (46)
"Great house! Small issue with getting into the place with the keybox, but was quickly resolved. We had a great time, it was so comfy, great place to come home after a long day of skiing, exploring, etc. Lots of room to spread out with the family and nighttime hot tub soaks in the cold air were so refreshing!"
Rustic home with a private hot tub, fireplace, cable, & washer/dryer
Property grounds
By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing.
9.8 out of 10, Exceptional, (57)
"We loved our stay at the lodge. We had two couples and kids ranging in age from 2 to 12. We did lots of skiing at Bromley but loved having Manchester so close to explore. The pinball arcade was a great rainy day activity for kids! The house was amazing and bigger than we imagined, we were all extremely comfortable. The only thing to mention is the stairs and upstairs loft are a bit scary for little ones. We blocked them with a baby gate and didn’t let the two year old up there, but it was fine...
By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing.
Interior
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
9.2 out of 10, Wonderful, (13)
"Great little cabin - really enjoyed our stay"
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
Exterior
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
Fridge, microwave, oven, stovetop
Ski-in/out sunrise condo with pool & hot tub - great ski retreat
9.0 out of 10, Wonderful, (69)
"Easy entry, lots of firewood for the fireplace. Very spacious."
Ski-in/out sunrise condo with pool & hot tub - great ski retreat
A heated pool
Luxe Plymouth Chalet w/ Indoor Pool & 3 Decks!
9.6 out of 10, Exceptional, (9)
"Listing details were accurate and house was very impressive upon arrival. Would love to stay at this property again! The onsite contact (Tanya) was very helpful with questions too."
Luxe Plymouth Chalet w/ Indoor Pool & 3 Decks!
Smart TV, fireplace, DVD player, ping pong
Beautiful Custom Built Timber Frame Home, Sleeps 11
10.0 out of 10, Exceptional, (94)
"Great house and host. We enjoyed the great room and fireplace. Snow was an extra! Will definitely book again."
Beautiful Custom Built Timber Frame Home, Sleeps 11
Outdoor spa tub
Spacious home Featuring a hot tub, fire pit, fireplace and more!
9.0 out of 10, Wonderful, (4)
"We had a pleasant experience staying at this space for our gathering. It provided a quiet environment conducive to our needs. The host was very friendly and responsive, addressing any inquiries promptly. It's a peaceful and accommodating venue."
The price is AU$1,494
per night
27 May - 28 May
Spacious home Featuring a hot tub, fire pit, fireplace and more!
Property grounds
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."
The price is AU$2,507
per night
26 May - 27 May
Perfect Reunion House w/fireplace & piano. Dogs welcome. Discounted ski tix at Bromley. Add private indoor pool on request.
Fridge, microwave, oven, stovetop
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)
Exterior
Stay Safe! Stay strong!
10.0 out of 10, Exceptional, (39)
"Spacious and clean accommodation. Beds are comfy and lots of toys & games for the kids. We forgot that there is no real kitchen but it was clearly mentioned in the posting."
Stay Safe! Stay strong!
TV, fireplace, DVD player, ping pong
Sweet chalet with private hot tub, firepit, game room & minibar
9.6 out of 10, Exceptional, (32)
"All good lots of fun"
Sweet chalet with private hot tub, firepit, game room & minibar
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See all available properties in Chester
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

Interior
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
Exterior
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
9.8 out of 10, Exceptional, (175)
"This was a great stay- thank you so much! The property was clean and serene, the house adorable and cozy and the hot tub is always a plus! It was a great area, we’ll have to visit again sometime :)"
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Fridge, microwave, oven, stovetop
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
9.6 out of 10, Exceptional, (30)
"My family really enjoyed this Lake House. The beautiful views of the lake were breathtaking. The house had everything we needed for preparing meals. The kitchen was functional and generally well equipped. The beds in the house were particularly comfortable. We enjoyed early morning coffee on the deck with perfect views of the lake. The location was great. Lots of wonderful hiking trials in close proximity. My only suggestion to the owners is to give the house a good deep cleaning. Nonetheless,...
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.

Chester Holiday Homes information

Number of reviews
864
Accommodation
922 Holiday Homes
Lowest Price
AU$657
Highest Price
AU$2,507

Recent Reviews in Chester
Expedia verified reviews