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Check prices for these dates

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8 Aug - 10 Aug
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15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sep - 28 Sep

Cottages in Chester

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

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

8.8 out of 10, Excellent, (53)
"Great place just need the fire place to be fixed asap, especially for the winter time"
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Exterior

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

9.6 out of 10, Exceptional, (225)
"Very cozy cabin for a weekend getaway. Multiple fireplaces with plenty of firewood available. Great place to curl up with a book or lots of shopping / restaurants in the area. "
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Woodstock Village Carriage House
Exterior

Woodstock Village Carriage House

9.6 out of 10, Exceptional, (92)
"Location was great!!"
Woodstock Village Carriage House
Home with a spring-fed pond and mountain view.
Exterior

Home with a spring-fed pond and mountain view.

10.0 out of 10, Exceptional, (117)
"Cute cottage with a lot of charm. The kiddos loved the concept of staying next to a pond. Convenient location to Manchester center and also to Bromley. Jeremy was quick to respond to all to all pf our questions."
Home with a spring-fed pond and mountain view.
The Cairn, 1840s Cozy Stone Cottage, Pet Friendly
Exterior

The Cairn, 1840s Cozy Stone Cottage, Pet Friendly

10.0 out of 10, Exceptional, (13)
"We very much enjoyed our stay in this historic, architecturally significant home. We would definitely stay here again."
The Cairn, 1840s Cozy Stone Cottage, Pet Friendly
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
Exterior

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

9.8 out of 10, Exceptional, (16)
"We loved the house and especially the location. The views are beautiful and the proximity to town, the mountain and parks make it a fantastic spot to stay."
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
Charming pet-friendly, Meadow View Cottage in heart of historic Dorset VT!
Exterior

Charming pet-friendly, Meadow View Cottage in heart of historic Dorset VT!

10.0 out of 10, Exceptional, (28)
"Loved Dorset and this house was great. Very clean and living area was nice to spend time with family. Also close to skiing which we took advantage of"
Charming pet-friendly, Meadow View Cottage in heart of historic Dorset VT!
Cozy cottage on the river, minutes from skiing, horse events, and so much more!
Exterior

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

10.0 out of 10, Exceptional, (7)
"very good cozy location. enjoyed the privacy during our stay."
Cozy cottage on the river, minutes from skiing, horse events, and so much more!
Rustic Marlboro Cottage: 4 Mi to Lake Raponda!
Exterior

Rustic Marlboro Cottage: 4 Mi to Lake Raponda!

3.0 star property
Rustic Marlboro Cottage: 4 Mi to Lake Raponda!
Near Skiing & Hiking: Quiet Home in West Wardsboro
Interior

Near Skiing & Hiking: Quiet Home in West Wardsboro

3.0 star property
Near Skiing & Hiking: Quiet Home in West Wardsboro
This cottage is a 0 bedroom(s), 1.5 bathrooms, located in Manchester, VT.
Exterior

This cottage is a 0 bedroom(s), 1.5 bathrooms, located in Manchester, VT.

10.0 out of 10, Exceptional, (28)
"This was a great location… close to town but also close to skiing, hiking and skating."
This cottage is a 0 bedroom(s), 1.5 bathrooms, located in Manchester, VT.
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
TV, books

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

10.0 out of 10, Exceptional, (7)
"Great, clean, charming cottage. The hosts are amazing and communicated every detail, very hospitable. Highly recommend. "
The price is SAR 972
SAR 1,201 total
includes taxes & fees
7 Aug - 8 Aug
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro
Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow
Exterior

Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow

9.6 out of 10, Exceptional, (64)
"We enjoyed our stay in this cozy cabin on the ridge. The owners have great taste and they have thought of everything to make the stay pleasant. "
Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow
'mount Pine' Getaway Near Green Mtn Nat'l Forest!
House (3 Bedrooms) | Interior

'mount Pine' Getaway Near Green Mtn Nat'l Forest!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Amazing place! Super clean and cozy, and host was extremely nice and communicative. Highly recommend."
'mount Pine' Getaway Near Green Mtn Nat'l Forest!
Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!
Interior

Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!

3.0 star property
Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!
Wilmington Retreat Near Trails, Skiing & Festivals
House (3 Bedrooms) | Interior

Wilmington Retreat Near Trails, Skiing & Festivals

3.0 star property
10.0 out of 10, Exceptional, (1)
"Would definitely recommend! House had an everything we would need. So comfy and cozy! "
Wilmington Retreat Near Trails, Skiing & Festivals
Peaceful Marlboro Vacation Rental w/ Sauna & Yard!
House (2 Bedrooms) | Interior

Peaceful Marlboro Vacation Rental w/ Sauna & Yard!

3.0 star property
Peaceful Marlboro Vacation Rental w/ Sauna & Yard!
Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
Exterior

Wilmington Home on 18 Acres ~ 9 Mi to Skiing!

3.0 star property
10.0 out of 10, Exceptional, (1)
Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
Ski & Lake Home-Minutes from Magic, Stratton, Bromley & Okemo-Southern Vermont
Terrace/patio

Ski & Lake Home-Minutes from Magic, Stratton, Bromley & Okemo-Southern Vermont

10.0 out of 10, Exceptional, (2)
"The Carriage House is lovely and surroundings beautiful. We had a very relaxing experience. Lizzie was a perfect host."
Ski & Lake Home-Minutes from Magic, Stratton, Bromley & Okemo-Southern Vermont
4 Mi to Mount Snow: West Dover Cabin w/ Game Room
House (5 Bedrooms) | Interior

4 Mi to Mount Snow: West Dover Cabin w/ Game Room

3.0 star property
4 Mi to Mount Snow: West Dover Cabin w/ Game Room
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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Top Chester Hotel Reviews

Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Bed was more comfortable than home. Dinner at Richardson’s Grill was fantastic. Breakfast buffet was mediocre. Room was very nice but bathroom needed updating."
Susan 2-night trip
Posted 2 days ago
Woodstock Inn & Resort

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