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Compare 123 Cottages in Chester with updated reviews, rates, and availability.

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

9.6 out of 10, Exceptional, (206)
"Perfect get away. "
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

Cozy 1850s home on the riverfront with mountain & river views - dog-friendly

9.4 out of 10, Exceptional, (16)
"We loved the cabin and its proximity to the town of Woodstock. Nice to come home at the end of the day. The only issue is the bedrooms are upstairs and the bathroom is downstairs….but we managed. Overall a great stay. "
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly

CHARMING 4-bedroom cottage in Weston, Vermont. CLOSE TO SKI RESORTS

2.0 star property
10.0 out of 10, Exceptional, (2)
"Rustic house was just what we wanted and needed. Good communication with owners and made a great stay"
CHARMING 4-bedroom cottage in Weston, Vermont. CLOSE TO SKI RESORTS

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

8.8 out of 10, Excellent, (44)
"A great little cabin close to Mt. Snow. Accurate description. Fire place didn’t work. Would stay here again. "
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

9.8 out of 10, Exceptional, (11)
"We loved the location and home! So close to Okemo, beautiful home right on the lake. The hottub and gas fireplace were appreciated after a day of skiing. We would definitely come back again!"
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

Vermont Country Cottage (Near Village)

9.2 out of 10, Wonderful, (10)
"This cottage reviewed very well online and pictures were very accurate too. It was secluded and far from neighbors, fire house across the street but zero activity the whole weekend. The cottage had the amenities listed. It was neat and tidy, well equipped. Very confortable. Loved the wood stove. We used that and it was wonderful. Check in/out Instructions were easy to follow. The area was beautiful, peacefu and not too far away from groceries, food or beverages. Would definitely go...
The price is SAR 656
SAR 1,445 total
includes taxes & fees
16 Mar - 17 Mar
Vermont Country Cottage (Near Village)

Charming Meadow View Cottage in heart of historic Dorset VT! Pet friendly!

10.0 out of 10, Exceptional, (26)
"Great spot for a small family. Three adults and two kids stayed for a couple nights. Nicely furnished and very clean."
Charming Meadow View Cottage in heart of historic Dorset VT! Pet friendly!

The Cairn, 1840s Cozy Stone Cottage, Pet Friendly

10.0 out of 10, Exceptional, (8)
"Close drive to Okemo. Quiet area. Very nice place to spend a weekend. Only con: Bottom floor is a bit drafty. "
The Cairn, 1840s Cozy Stone Cottage, Pet Friendly

This cottage is a 1 bedroom(s), 1.5 bathrooms, located in Manchester, VT.

10.0 out of 10, Exceptional, (27)
"Close to Bromley and StrattonWarm, cozy, clean cottage"
This cottage is a 1 bedroom(s), 1.5 bathrooms, located in Manchester, VT.

Cottage 7min to Ski Stratton-Wood Stove,Starry Skies,Fire Pit,Views,Dogs OK

2.0 star property
10.0 out of 10, Exceptional, (1)
"The property was clean and neat. Very quaint and in the woods. We had a great time. Looking forward to doing it again in the near future. "
Cottage 7min to Ski Stratton-Wood Stove,Starry Skies,Fire Pit,Views,Dogs OK

Perfect Country Cottage

9.6 out of 10, Exceptional, (78)
"Host was great! On top of everything involved with the trip. The house worked out great for our ski trip. "
Perfect Country Cottage

Cozy cottage on the river, minutes from skiing, horse events, and so much more!

10.0 out of 10, Exceptional, (7)
"We loved our stay at the Dark Horse Cottage. It was close to everything we wanted to do. We loved being near the little creek. They thought of everything for amenities. It was perfect for what we needed. "
Cozy cottage on the river, minutes from skiing, horse events, and so much more!

Cozy Historic Hilltop Cottage with Mount Ascutney View

9.8 out of 10, Exceptional, (76)
"This was the perfect cottage for a winter getaway. I was solo, but the home could have easily accommodated many more. I loved the vintage touches and had a nice time listening to the classic vinyl records while enjoying a glass of wine and watching it snow. I had dinner outside on the patio one night and the view was lovely. It is just a few minutes drive from Woodstock and Quechee and I visited both several times. The cottage was clean and had everything I needed. Highly recommend for a quiet,...
Cozy Historic Hilltop Cottage with Mount Ascutney View

Home with a spring-fed pond and mountain view.

10.0 out of 10, Exceptional, (113)
"My family and I stayed at this property over the weekend. We have two children, 12 and 9 and 3 dogs. The space was absolutely perfect for us. The trundle bed in the living room was great to allow both kids to have their own sleeping space. Everything you can possibly imagine is stocked in this house so if you forget something, chances are you will find it upon check in. The kitchen has all of the utensils and cooking tools you need. The host provides a lot of menus, maps and magazines about what...
Home with a spring-fed pond and mountain view.

Cottage in Private Village On VT-100 (5-min to Mount Snow)

9.0 out of 10, Wonderful, (2)
"This cottage was wonderful! Great location. Great shower. Loved having a kitchen. Bed was comfortable and place was clean! The only real downfall was the couch/ seating arrangement! After a long day on mountain a nice couch or chair is where it's at! The couch was small and uncomfortable but our little family made the best of it ! Communication was always there and we were overall pleased ! "
Cottage in Private Village On VT-100 (5-min to Mount Snow)

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

10.0 out of 10, Exceptional, (6)
"The property is cute and well kept. The owners were very nice and welcomed us with delicious home made blueberry muffins that my sons and I very much appreciated. Great directions and communication and very nice place to spend a weekend! "
The price is SAR 982
SAR 1,175 total
includes taxes & fees
17 Feb - 18 Feb
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!

3.0 star property
Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!

Weston Vacation Rental - Close to Ski Resorts!

3.0 star property
Weston Vacation Rental - Close to Ski Resorts!

Hike & Swim On-site: Cozy Falls Brook Cabin

3.0 star property
10.0 out of 10, Exceptional, (1)
"This is exactly how it’s described- perfect cozy spot- babbeling brook to keep you company while sitting on the porch - fire pit for cozy evenings and cabin inside is perfection- cozy cozy cozy!! Matt was the perfect host and readily available- hoping to return!! 15 mins from farmers markets, covered bridges, shops, food, drinks and entertainment ❤️"
Hike & Swim On-site: Cozy Falls Brook Cabin

Inviting Vermont Home On Mount Ascutney!

3.0 star property
Inviting Vermont Home On Mount Ascutney!
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 1,546
SAR 1,922 total
includes taxes & fees
2 Mar - 3 Mar
Long Trail House at Stratton Mountain Resort

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

9.6 out of 10, Exceptional, (206)
"Perfect get away. "
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
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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