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Compare 119 Cottages in Chester with updated reviews, rates, and availability.

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

9.6 out of 10, Exceptional, (204)
"… And it remains a gem! We lucked out w/a foot of snow on Thanksgiving and so kept the fires burning. Just a great, special place."
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

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

2.0 star property
10.0 out of 10, Exceptional, (1)
"The property is well maintained, clean and has a lot of charm. The backyard offers a stunning view of the mountains, a stream and quaint cottages dotting the landscape. The only surprise was the location on a major roadway. Backing into the driveway can be difficult especially after dark. Otherwise we would highly recommend this home. Andrew the property manager was friendly and helpful. "
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, (43)
"Cabin was perfect for our long weekend. Master bed mattress needs an update, but otherwise everything was fantastic."
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Vermont Country Cottage (Near Village)

10.0 out of 10, Exceptional, (9)
"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 AED 680
AED 1,461 total
includes taxes & fees
8 Jan - 9 January 2025
Vermont Country Cottage (Near Village)

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

10.0 out of 10, Exceptional, (23)
"My husband and I stayed at the cottage with our black lab while visiting family in Dorset. The house is located in the village but is quite private and has a nice meadow behind for anyone with a dog. Everything was perfect and Nicole was very accommodating. We hope to stay again."
Charming Meadow View Cottage in heart of historic Dorset VT! Pet friendly!

Cozy Crescent Cottage

10.0 out of 10, Exceptional, (24)
"This was our second stay at the cozy cottage amd was just as enjoyable as the first time . Glenn and Melanie are very responsive and like to makesure their guests are comfortable and happy . We loved waking up on the lake and enjoyed the back deck and firepit. We look forward to renting here again in the future. P"
Cozy Crescent Cottage

Charming Cavendish Cottage: All-Season Retreat!

2.0 star property
10.0 out of 10, Exceptional, (4)
"Such a wonderful and warm home. Other than condiments the kitchen was well stocked with dishes, cups and small appliances. The back screened in porch was a peaceful retreat for morning coffee and devotions and a great place to wind down at night. The owner was very nice and accommodating. The minute we walked in we were in awe of Rosehill Cottage. We will definitely stay here again if we are in the area."
Charming Cavendish Cottage: All-Season Retreat!

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

9.2 out of 10, Wonderful, (15)
"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

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

9.6 out of 10, Exceptional, (9)
"This lake house is absolutely everything you would expect from a five star rated home. It is a newly renovated lake front home. The house is located about 3 miles north of Ludlow. The property was clean and well maintained. We visited on Columbus Day weekend for our daughter’s wedding. We will return some day in the summer to enjoy the lake. I would recommend this property to my family and friends. Thank you for sharing your home with us during this special time for our family. "
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

Home with a spring-fed pond and mountain view.

10.0 out of 10, Exceptional, (110)
"Very nice and cozy place to getaway for a few nights! Very close to Manchester and places to eat and things to do. Koi pond was very pretty and we enjoyed feeding them! Loved having coffee on the deck with a view of the mountains, before we went on our adventures! "
Home with a spring-fed pond and mountain view.

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

10.0 out of 10, Exceptional, (24)
"Enjoyed our stay! Great location! Would stay again!"
This cottage is a 1 bedroom(s), 1.5 bathrooms, located in Manchester, VT.

Cozy Historic Hilltop Cottage with Mount Ascutney View

9.6 out of 10, Exceptional, (75)
"This house is exactly as described. It is in a very attractive location with good views and is very private. The house is much larger inside than it appears from the photos but still very cozy and is well equipped. It was spotlessly clean."
Cozy Historic Hilltop Cottage with Mount Ascutney View

The Cairn, 1840s Cozy Stone Cottage, Pet Friendly

10.0 out of 10, Exceptional, (7)
"Everything was wonderful from the very beginning… The ease of booking, payment, check-in, property, check out, it was all perfect! The house was in a great neighborhood, very quaint, and just the perfect size for the six of us. Well maintained and clean, had everything we could possibly need. Highly recommend."
The Cairn, 1840s Cozy Stone Cottage, Pet Friendly

Spruce Moose Cottage | Tiny House on 65 private acres

Spruce Moose Cottage | Tiny House on 65 private acres

Cozy farm cottage on gorgeous landscape, quiet but close to s. NH/VT attractions

10.0 out of 10, Exceptional, (5)
"Short time we had there but everything was great would love to stay again for personal trip and see more of the farm "
The price is AED 896
AED 1,079 total
includes taxes & fees
1 Jan - 2 January 2025
Cozy farm cottage on gorgeous landscape, quiet but close to s. NH/VT attractions

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!

4bdrm Cottage central to year round fun w/fireplace

4bdrm Cottage central to year round fun w/fireplace

Cozy Falls Brook Cabin: Hike & Swim On-site!

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 ❤️"
Cozy Falls Brook Cabin: Hike & Swim On-site!

'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!

Idyllic Wallingford Retreat - Near Skiing & Hiking

3.0 star property
Idyllic Wallingford Retreat - Near Skiing & Hiking
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

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 AED 1,304
AED 1,621 total
includes taxes & fees
8 Jan - 9 January 2025
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

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

9.8 out of 10, Exceptional, (164)
"The property is exactly like the pictures indicate. The house is in a friendly neighborhood outside of town. The house is very comfortable and spacious. The host responds to your messages in timely manner, and, she is very workable. Would definitely stay there again "
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
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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