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Compare 61 Cottages in West Chesterfield with updated reviews, rates, and availability.

Property grounds
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
9.2 out of 10, Wonderful, (23)
"Awesome cabin, fireplace was amazing. Spacious open and a great place to spend time and relax"
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Exterior
Waterfront Cottage on Scenic Sportsman Pond
9.4 out of 10, Exceptional, (34)
"Linda was wonderful in her review of the property and was very accommodating in all aspects of our stay. The cottage was well equipped and very comfortable including the mattress. We enjoyed the lake and a little fishing. The area is very nice and we did some exploring. It was very quiet and we rarely even saw anyone while we were on the lake. We hope to return in the spring or summer. Many thanks to Linda and Brad"
Waterfront Cottage on Scenic Sportsman Pond
Exterior
Cozy Cottage Along Idyllic Green River
10.0 out of 10, Exceptional, (32)
"Perfect litle getaway. Not to far from town, beautiful surrounding area, exactly what i was looking for."
Cozy Cottage Along Idyllic Green River
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Exterior
Lakeside living! Relax and enjoy prestine Granite Lake…..your oasis to breathe
Lakeside living! Relax and enjoy prestine Granite Lake…..your oasis to breathe
Interior
Cozy Falls Brook Cabin: Hike & Swim On-site!
3.5 star property
Cozy Falls Brook Cabin: Hike & Swim On-site!
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!
Interior
Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!
3.5 star property
10.0 out of 10, Exceptional, (1)
"We had a truly wonderful stay. The cottage and property are beautiful, peaceful and very special. Great views! Our host thought of everything, it's very comfortable and lovely. Best place to stay in Southern Vermont! Don't miss the Tiny Bread Box on Saturdays; it's just up the road. We'll defiantly be back for another visit."
Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!
Interior
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
3.5 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!
Interior
Jacksonville Cabin w/ Wraparound Deck & Views
3.0 star property
Jacksonville Cabin w/ Wraparound Deck & Views
Interior
Cozy Treetop Hideaway Near Harriman Reservoir!
3.5 star property
Cozy Treetop Hideaway Near Harriman Reservoir!
Interior
Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
3.5 star property
10.0 out of 10, Exceptional, (1)
Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
Interior
Wilmington Home w/ Pool Access, 20 Mins to Mt Snow
3.5 star property
10.0 out of 10, Exceptional, (1)
"Owner Brent was helpful and quick to respond to questions. The house is near Mount Snow great for skiing! Very nice place to stay, we will definitely stay again when booking for next year."
Wilmington Home w/ Pool Access, 20 Mins to Mt Snow
Interior
Historic New Hampshire Home: 1 Mi to Boat Launch
3.0 star property
Historic New Hampshire Home: 1 Mi to Boat Launch
Interior
Chic Wilmington Retreat w/ Deck: Walk to Downtown!
3.0 star property
Chic Wilmington Retreat w/ Deck: Walk to Downtown!
Interior
Peaceful Marlboro Vacation Rental w/ Sauna & Yard!
3.0 star property
Peaceful Marlboro Vacation Rental w/ Sauna & Yard!
Interior
Cozy 'green Mountain Chalet' in Putney Town
3.0 star property
Cozy 'green Mountain Chalet' in Putney Town
Interior
Family Winter Retreat w/ Hot Tub ~14 Mi to Slopes!
3.5 star property
Family Winter Retreat w/ Hot Tub ~14 Mi to Slopes!
Interior
Spacious Dover Home w/ Sauna < 5 Miles to Ski!
3.0 star property
10.0 out of 10, Exceptional, (1)
"we enjoyed all of the space and the location a short distance from the resort. very comfortable stay for a group of five."
Spacious Dover Home w/ Sauna < 5 Miles to Ski!
Interior
West Dover Getaway w/ Hot Tub: Near Mt Snow!
3.0 star property
West Dover Getaway w/ Hot Tub: Near Mt Snow!
Interior
Cozy Vermont Escape w/ Deck, Near Skiing!
3.0 star property
Cozy Vermont Escape w/ Deck, Near Skiing!
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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 West Chesterfield

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
Property grounds
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
9.2 out of 10, Wonderful, (23)
"Awesome cabin, fireplace was amazing. Spacious open and a great place to spend time and relax"
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Property grounds
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
10.0 out of 10, Exceptional, (192)
"Our family rated this as our best stay in 7 years of traveling with VRBO properties. There was lots of room for everyone to spread-out, but the family spent most of the time in the game room playing pool, fuzzball, shuffleboard and Ping-Pong. Overall and great spring break for the family and friends."
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
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.

West Chesterfield Cottages information

Number of reviews
90
Accommodation
61 Cottages
Lowest Price
Highest Price

Frequently asked questions

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Reserving a cottage in West Chesterfield is as simple as entering your travel dates and selecting your ideal place for a vacation in nature. From high-end retreats to budget-friendly stays and cottages that come with perks like free WiFi, Expedia has something for all styles. As for unbeatable deals? We’ve got them too!
How can I find cheap cottages in West Chesterfield?
Expedia can help you track down cheap cottages in West Chesterfield. To find your perfect stay in a couple of quick clicks, use our convenient filter tool to tailor your search results by star rating, amenities and budget.
What is there to do in West Chesterfield near my cottage?
You’ll find plenty of fantastic things to do in West Chesterfield. Check out major attractions like Brattleboro Bowl, Brattleboro Museum & Art Center and Fort Dummer State Park. Pisgah State Park, Actors Theatre Playhouse and Next Stage Arts are also visitor favorites.

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