A stone archway surrounded by lush greenery and trees.

West Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for West Chesterfield vacation rentals

Terrace/patio

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Hinsdale
10.0 out of 10, Exceptional, (15 reviews)
"Very enjoyable getaway weekend!!"
United States
Adrienne
The price is ￥19,062
￥30,507 total
includes taxes & fees
Jul 15 - Jul 16
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Interior

Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (59 reviews)
"Beautiful, thoughtful space on a gorgeous piece of property. "
United States
Jodi W.
The price is ￥18,860
￥32,863 total
includes taxes & fees
Jul 26 - Jul 27
Lovely 2nd Floor Apartment
Outdoor pool, a heated pool

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Location was excellent, hosts were responsive, cozy little place with the fireplace, great stay!"
United States
Tania J.
The price is ￥11,001
￥52,807 total
includes taxes & fees
Jul 20 - Jul 21
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Fridge, microwave, stovetop, coffee/tea maker

Hiking Trails On-Site: Cozy Falls Brook Cabin

Hiking Trails On-Site: Cozy Falls Brook Cabin
Dummerston
10.0 out of 10, Exceptional, (18 reviews)
"So cozy, perfect Vermont vacation!"
United States
Evan S.
The price is ￥22,150
￥69,716 total
includes taxes & fees
Aug 5 - Aug 6
Hiking Trails On-Site: Cozy Falls Brook Cabin
Exterior

Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (12 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is ￥19,701
￥72,464 total
includes taxes & fees
Jul 19 - Jul 20
Chalet Mount Snow/Stratton Skiing/hiking
Outdoor dining

2 private mountain RV pads for rent. Full hook ups

2 private mountain RV pads for rent. Full hook ups
Winchester
The price is ￥8,892
￥13,157 total
includes taxes & fees
Aug 10 - Aug 11
2 private mountain RV pads for rent. Full hook ups
Smart TV, fireplace, Netflix, streaming services

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Dover
9.6 out of 10, Exceptional, (27 reviews)
"Very clean - kitchen well stocked with utensils for cooking - great proximity to Mount Snow."
United States
Brian S.
The price is ￥17,287
￥71,055 total
includes taxes & fees
Jul 15 - Jul 16
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Lobby

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Dover
8.6 out of 10, Excellent, (37 reviews)
"Location was fantastic! Great ski-in, ski-out location! Unit itself was very dated but location made up for it."
United States
Evan C.
The price is ￥16,976
￥58,497 total
includes taxes & fees
Jul 20 - Jul 21
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
House (2 Bedrooms) | Interior

Hiking Trails On-site: Cozy Falls Brook Cabin

Hiking Trails On-site: Cozy Falls Brook Cabin
3.0 star property
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"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 ❤️"
United States
sarah
The price is ￥29,264
￥66,392 total
includes taxes & fees
Aug 5 - Aug 6
Hiking Trails On-site: Cozy Falls Brook Cabin
Beach

Cozy 3 bedroom condo 2.5 miles to Mount Snow

Cozy 3 bedroom condo 2.5 miles to Mount Snow
West Dover
9.2 out of 10, Wonderful, (52 reviews)
"Fire place was awesome! Great place to stay! Had everything in the kitchen we needed. All the beds were comfy! "
United States
Susan S.
The price is ￥13,451
￥46,222 total
includes taxes & fees
Jul 28 - Jul 29
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Property grounds

Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (61 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is ￥29,102
￥52,875 total
includes taxes & fees
Jul 20 - Jul 21
Family Friendly Hilltop House In Putney Vermont
Terrace/patio

Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is ￥44,462
￥54,999 total
includes taxes & fees
Jul 15 - Jul 16
Vikings Villages Resort - Double Bed Room
Interior

The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!

The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
Wardsboro
10.0 out of 10, Exceptional, (9 reviews)
"Loved this place so much! Adorable spot, quaint but has everything you need. Loved the luxury details. "
United States
Carly L.
The price is ￥30,053
￥80,403 total
includes taxes & fees
Jul 15 - Jul 16
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
Property grounds

Dover Summer Specials-Barrel Sauna, Fire Pit, Hot Tub, Game Room, Dogs Welcome!

Dover Summer Specials-Barrel Sauna, Fire Pit, Hot Tub, Game Room, Dogs Welcome!
Dover
10.0 out of 10, Exceptional, (10 reviews)
"Awesome place, fantastic amenities and easy to get to. Looking forward to coming back."
United States
Connor S.
The price is ￥29,528
￥90,638 total
includes taxes & fees
Jul 15 - Jul 16
Dover Summer Specials-Barrel Sauna, Fire Pit, Hot Tub, Game Room, Dogs Welcome!
Terrace/patio

Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Wardsboro
10.0 out of 10, Exceptional, (19 reviews)
"Cute place, very pet-friendly."
United States
Jeff H.
The price is ￥28,429
￥70,123 total
includes taxes & fees
Aug 4 - Aug 5
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Private kitchen

The Studio with a View. Bring your dog, too!

The Studio with a View. Bring your dog, too!
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"Great cozy little mountain cabin stay!! Well-appointed studio barn/cabin with scenic view and great proximity to skiing. Would stay again : )"
United States
James M.
The price is ￥27,617
￥52,036 total
includes taxes & fees
Aug 4 - Aug 5
The Studio with a View. Bring your dog, too!
Fridge, microwave, oven, stovetop

Modern Downtown Escape HotTub Fire Pit Games 12ppl

Modern Downtown Escape HotTub Fire Pit Games 12ppl
Keene
9.4 out of 10, Exceptional, (25 reviews)
"Amazing property and just what we needed for a recharging weekend!"
United States
Jackie D.
The price is ￥25,545
￥51,160 total
includes taxes & fees
Jul 15 - Jul 16
Modern Downtown Escape HotTub Fire Pit Games 12ppl
Dining

VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Wilmington
10.0 out of 10, Exceptional, (19 reviews)
"Great place!"
United States
Jack & Heather G.
The price is ￥33,306
￥94,704 total
includes taxes & fees
Jul 21 - Jul 22
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Property grounds

A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST

A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST
West Dover
9.0 out of 10, Wonderful, (4 reviews)
"Clean, comfortable, our 2nd time staying here - very nice."
United States
Dan G.
The price is ￥38,176
￥105,661 total
includes taxes & fees
Jul 16 - Jul 17
A-Frame Cabin w/ Hot Tub Near Mt. Snow & VAST
Outdoor spa tub

Chalet 1mi to Mount Snow with cinema and hot tub

Chalet 1mi to Mount Snow with cinema and hot tub
Dover
10.0 out of 10, Exceptional, (12 reviews)
"Awesome stay!"
United States
Liz E.
The price is ￥38,891
￥144,542 total
includes taxes & fees
Jul 19 - Jul 20
Chalet 1mi to Mount Snow with cinema and hot tub
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 West Chesterfield Hotel Reviews

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent
"We had a great stay overall. The hotel was clean, well-maintained, and the staff was friendly, welcoming, and courteous throughout our visit. Breakfast was good, but the pancake station became backed up during the busy morning rush. Adding a second pancake machine would help reduce the wait and make the breakfast experience even better. We would definitely stay here again."
michele 1-night trip
Posted 13 hours ago
Keene Elm City Hotel, an Ascend Collection Hotel

Find out more about West Chesterfield

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Frequently asked questions

Can I find a vacation rental in West Chesterfield?

Yes, you can find vacation rentals close to popular sights in West Chesterfield, or you can select a more secluded option if you'd like a relaxing place to stay. Nature enthusiasts will enjoy the riverfront in West Chesterfield. Make sure you have time to check out the entertainment choices and theaters during your trip.

What's the top vacation rental that West Chesterfield has to offer?

Bright three-level home with water views, jetted tub, firepit, and pool table: Visitors like this West Chesterfield vacation home rental. It is located in the mountains and has a fireplace, a garden, and laundry facilities to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the pool table in this rental home to help you unwind.

What’s there to see and do in West Chesterfield?

Madame Sherri Forest and Connecticut River are a couple of scenic spots to enjoy the outdoors, whereas Actors Theatre Playhouse is one of the cultural attractions. While here, United States Navy Seabee Bridge and Madame Sherris Castle Ruins are other places worth a visit.

What’s a vacation rental in West Chesterfield like?

Vacation rentals are private properties you can stay in for several days or longer in West Chesterfield. Vacation rentals offer amenities like kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitized environment, a vacation rental can offer a sense of security away from public hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for families.