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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$575 per night from 25 Mar to 26 Mar
AU$575
includes taxes & fees
25 Mar - 26 Mar
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!
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.
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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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
New! Family Townhome with Hot Tub, Shuttle service

New! Family Townhome with Hot Tub, Shuttle service

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.
New! Family Townhome with Hot Tub, Shuttle service
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
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!
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
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
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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
366 Holiday Homes
Lowest Price
AU$184
Highest Price
AU$575
Popular accommodation
Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!, Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit. , Ski-In condo at Mount Snow with Fireplace, Bears Crossing, Spacious Townhome with breathtaking views of Mount Snow. 5 min Shuttle to ski, New! Family Townhome with Hot Tub, Shuttle service, Mountain-view home near the slopes with at-home entertainment - dog-friendly, Wilmington Vacation Rental Near Hiking and Skiing!, Cozy retreat near slopes, Forest Home with Shared Pool & Hot Tub, WiFi, & Washer/Dryer - One Small Dog OK

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$245 per night from 2 Mar to 3 Mar
AU$245
includes taxes & fees
2 Mar - 3 Mar
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
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$234 per night from 4 Mar to 5 Mar
AU$234
includes taxes & fees
4 Mar - 5 Mar
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
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$189 per night from 24 Feb to 25 Feb
AU$189
includes taxes & fees
24 Feb - 25 Feb
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
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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$184 per night from 3 Mar to 4 Mar
AU$184
includes taxes & fees
3 Mar - 4 Mar
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.