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Compare 117 Cottages in Chester with updated reviews, rates, and availability.

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Secluded covered entry

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

9.6 out of 10, Exceptional, (200)
"Of all the rental cabons I've enjoyed over many years, ths one was at the top. Private, quiet and relaxing,,,so much so that I chose to forgo a day of fishing just to enjoy a warm peaceful fire. My thanks to the property manager for his welcoming, helpful & accommodating efforts. Thank you! Richard"
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly

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

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

9.0 out of 10, Wonderful, (42)
"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)
Exterior

Vermont Country Cottage (Near Village)

10.0 out of 10, Exceptional, (8)
"The house was so well stocked and in a great location. We were inly there for less than 24 hours but it was cozy and comfortable and overall great vibes as soon as you walk in! "
The price is AED 459
AED 1,179 total
includes taxes & fees
1 Dec - 2 Dec
Vermont Country Cottage (Near Village)
CHARMING 4-bedroom cottage in Weston, Vermont. CLOSE TO SKI RESORTS
Terrace/patio

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
Cozy Historic Hilltop Cottage with Mount Ascutney View
Cottage on the hill

Cozy Historic Hilltop Cottage with Mount Ascutney View

9.6 out of 10, Exceptional, (74)
"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
Charming Meadow View Cottage in heart of historic Dorset VT! Pet friendly!
Cottage charm! The Front Cottage at MeadowView

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

10.0 out of 10, Exceptional, (22)
"Meadow View Cottage is everything it is advertised as and more! There is so much attention to detail that I literally felt at home. Everything is just where one might look for it. The owner was thoughtful and helpful and we hope to stay again when we visit Dorset!"
Charming Meadow View Cottage in heart of historic Dorset VT! Pet friendly!
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

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.
Terrace/patio

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.
"Great location, comfortable, and spacious. A great home base for a fly-fishing trip to southern Vermont!" - Taylor, *****

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.
The Cairn, 1840s Cozy Stone Cottage, Pet Friendly
Exterior

The Cairn, 1840s Cozy Stone Cottage, Pet Friendly

10.0 out of 10, Exceptional, (6)
"This property was exactly as pictured and the owner was quick in communicating with us in both getting needed information to us and responding to any concerns we had. We enjoyed looking up the history of the cottage's stone work and everything about our stay here and in this lovely town. Very charming and well maintained property. We look forward to possibly staying here again if our future travels bring us back through Chester, VT. "
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

Spruce Moose Cottage | Tiny House on 65 private acres
Ski & Lake Home-Minutes from Magic, Stratton, Bromley & Okemo-Southern Vermont
Lake

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

10.0 out of 10, Exceptional, (2)
"We had the BEST time on our short little getaway to the Vermont mountains! We are very familiar with the area but this was our first VRBO. We didn’t really know what to expect but Lizzie’s place was absolutely perfect for our family of 5 (kids ages 2,5 and 7.) The space was cleaner than clean (which is a big deal to us) and updated. It is such a cute and happy little place and we didn’t want to leave. The kids loved the bunk beds, and the rooms couldn’t have been more comfortable and well...
Ski & Lake Home-Minutes from Magic, Stratton, Bromley & Okemo-Southern Vermont
Cozy farm cottage on gorgeous landscape, quiet but close to s. NH/VT attractions
d4dfddeb-ca93-4c46-84bb-9f6f05aa287b

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 1,086 total
includes taxes & fees
2 Dec - 3 Dec
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!
Living area

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
Exterior

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!
Living area

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!
Outdoor dining

'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
Dining

Idyllic Wallingford Retreat - Near Skiing & Hiking

3.0 star property
Idyllic Wallingford Retreat - Near Skiing & Hiking
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Terrace/patio

Charming Wilmington Cabin, 8 Mi. to Mt Snow!

3.0 star property
10.0 out of 10, Exceptional, (1)
"The house was everything we wanted and more. Loaded with space, kitchen supplies, comfort, a grill, gorgeous stone fireplace. The location on. sleepy back road in the woods was beautiful and quiet. The only complaint is that they make you take your trash with you when you go. There was a pass for the local dump which helped offset the inconvenience. Otherwise, A+"
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
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

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Front of property

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (39)
"Everything was wonderful. Easy in and out. Near to almost everything. Beautiful area. I left my keys by mistake and they were wonderful in getting them back to me. I would stay there again. "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Outdoor spa tub

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (196)
"It was a wonderful little cabin that was clean and decorated comfortably. It had everything we needed. The hot tub was delightful! "
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off! Free Pool
Located in the Okemo Mt. Community, a mile to the base lodge

Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off! Free Pool

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 "
Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off! Free Pool
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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