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Featured Holiday Homes in West Chesterfield

Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!

Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!

Dover
The price is AU$1,654 per night from 2 Feb to 3 Feb
AU$1,654
includes taxes & fees
2 Feb - 3 Feb
With a stay at this vacation home in West Dover, you'll be in the mountains, within a 5-minute drive of Mount Snow and Green Mountain National Forest.
Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!
Spacious Townhome with breathtaking views of Mount Snow. 5 min Shuttle to ski

Spacious Townhome with breathtaking views of Mount Snow. 5 min Shuttle to ski

Dover
With a stay at this vacation home in West Dover, you'll be next to a golf course, within a 5-minute drive of Mount Snow and North Branch Deerfield River.
Spacious Townhome with breathtaking views of Mount Snow. 5 min Shuttle to ski
Ski-In condo at Mount Snow with Fireplace, Bears Crossing

Ski-In condo at Mount Snow with Fireplace, Bears Crossing

Dover
With a stay at this vacation home in West Dover, you'll be in the mountains, within a 5-minute drive of Mount Snow and Green Mountain National Forest.
Ski-In condo at Mount Snow with Fireplace, Bears Crossing
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Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

Dover
When you stay at this vacation home in West Dover, you'll be in the mountains, within a 15-minute walk of Mount Snow and Green Mountain National Forest.
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
Wilmington Vacation Rental Near Hiking and Skiing!

Wilmington Vacation Rental Near Hiking and Skiing!

Wilmington
Located in Wilmington, this vacation home is a 1-minute drive from Green Mountain National Forest and 7 minutes from North Branch Deerfield River.
Wilmington Vacation Rental Near Hiking and Skiing!
Mountain-view home near the slopes with at-home entertainment - dog-friendly

Mountain-view home near the slopes with at-home entertainment - dog-friendly

West Dover
With a stay at this vacation home in West Dover, you'll be within a 5-minute drive of Mount Snow and Green Mountain National Forest.
Mountain-view home near the slopes with at-home entertainment - dog-friendly
Forest Home with Shared Pool & Hot Tub, WiFi, & Washer/Dryer - One Small Dog OK

Forest Home with Shared Pool & Hot Tub, WiFi, & Washer/Dryer - One Small Dog OK

Wilmington
Located in Wilmington, this vacation home is in a rural location, a 1-minute drive from Green Mountain National Forest and 7 minutes from North Branch Deerfield ...
Forest Home with Shared Pool & Hot Tub, WiFi, & Washer/Dryer - One Small Dog OK
Cozy retreat near slopes

Cozy retreat near slopes

Dover
With a stay at this vacation home in West Dover, you'll be within a 5-minute drive of Mount Snow and Green Mountain National Forest.
Cozy retreat near slopes
 500ft across the street to Carnitha. Gromet to main lift or take Moover to Base

500ft across the street to Carnitha. Gromet to main lift or take Moover to Base

Dover
When you stay at this vacation home in West Dover, you'll be in the mountains, within a 15-minute walk of Mount Snow and Green Mountain National Forest.
500ft across the street to Carnitha. Gromet to main lift or take Moover to Base
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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.

West Chesterfield Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our West Chesterfield vacation homes are the perfect way for you to wing it.

Holiday houses in West Chesterfield let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of West Chesterfield in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local West Chesterfield adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in West Chesterfield with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of West Chesterfield vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

West Chesterfield Holiday Homes essential information

Accommodation
356 Holiday Homes
Lowest Price
AU$181
Highest Price
AU$1,654
Popular accommodation
Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!, Spacious Townhome with breathtaking views of Mount Snow. 5 min Shuttle to ski, Ski-In condo at Mount Snow with Fireplace, Bears Crossing, Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit. , Wilmington Vacation Rental Near Hiking and Skiing!, Mountain-view home near the slopes with at-home entertainment - dog-friendly, Forest Home with Shared Pool & Hot Tub, WiFi, & Washer/Dryer - One Small Dog OK, Cozy retreat near slopes, 500ft across the street to Carnitha. Gromet to main lift or take Moover to Base

Top trending hotels in West Chesterfield

Riverside Hotel, Ascend Hotel Collection

Riverside Hotel, Ascend Hotel Collection

2.5 out of 5
20 Riverside Drive, West Chesterfield, NH
Fully refundableReserve now, pay when you stay
The price is AU$248 per night from 6 Feb to 7 Feb
AU$248
includes taxes & fees
6 Feb - 7 Feb
With a stay at Riverside Hotel, Ascend Hotel Collection in West Chesterfield, you'll be in the historical district, just a 4-minute walk from Connecticut River ...
Riverside Hotel, Ascend Hotel Collection
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is AU$191 per night from 26 Jan to 27 Jan
AU$191
includes taxes & fees
26 Jan - 27 Jan
A stay at Colonial Motel And Spa places you in the heart of Brattleboro, steps from Brattleboro Bowl and 11 minutes by foot from New England Center for Circus ...
Colonial Motel And Spa
Mountaineer Inn

Mountaineer Inn

2 out of 5
270 Handle Rd, West Dover, VT
Fully refundableReserve now, pay when you stay
The price is AU$278 per night from 27 Jan to 28 Jan
AU$278
includes taxes & fees
27 Jan - 28 Jan
When you stay at Mountaineer Inn in West Dover, you'll be near ski lifts, within a 15-minute walk of Mount Snow and Green Mountain National Forest.
Mountaineer Inn
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Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
1186 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is AU$181 per night from 27 Jan to 28 Jan
AU$181
includes taxes & fees
27 Jan - 28 Jan
When you stay at Comfort Inn & Suites Brattleboro I-91 in Brattleboro, you'll be near ski lifts, within a 10-minute walk of Connecticut River and United States ...
Comfort Inn & Suites Brattleboro I-91
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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.

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^Subject to availability and chosen travel dates.