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Featured Holiday Homes in West Chesterfield

Cozy, charming mountain home.

Cozy, charming mountain home.

Wardsboro
With a stay at this vacation home in Wardsboro, you'll be within a 15-minute drive of Mount Snow and Green Mountain National Forest.
Cozy, charming mountain home.
Dog-friendly chalet cabin with valley view, deck, and private hot tub

Dog-friendly chalet cabin with valley view, deck, and private hot tub

Wardsboro
With a stay at this vacation home in Wardsboro, you'll be within a 15-minute drive of Mount Snow and Green Mountain National Forest.
Dog-friendly chalet cabin with valley view, deck, and private hot tub
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

Whitingham
Located in Whitingham, this vacation home is on the waterfront, within a 15-minute walk of Harriman Reservoir and Green Mountain National Forest.
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
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Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

Townshend
Located in Townshend, this vacation home is on the waterfront, a 1-minute drive from West River and 8 minutes from Townshend State Park.
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
New Chalet mins to Mt with Hot tub

New Chalet mins to Mt with Hot tub

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 Chalet mins to Mt with Hot tub
Walk to Ski Lift: Spacious Condo in West Dover!

Walk to Ski Lift: Spacious Condo in West Dover!

2 out of 5
West Dover
With a stay at this vacation home in West Dover, you'll be within a 15-minute walk of Mount Snow and Green Mountain National Forest.
Walk to Ski Lift: Spacious Condo in West Dover!
West Dover Townhome Near Mount Snow Shuttle Stop!

West Dover Townhome Near Mount Snow Shuttle Stop!

2 out of 5
West Dover
With a stay at this vacation home in West Dover, you'll be within a 5-minute drive of Mount Snow and North Branch Deerfield River.
West Dover Townhome Near Mount Snow Shuttle Stop!
Wilmington Family Escape!  King Beds, Sleeps 13, Air hockey, Nerfgun Fun

Wilmington Family Escape! King Beds, Sleeps 13, Air hockey, Nerfgun Fun

Wilmington
With a stay at this vacation home in Wilmington, you'll be within a 10-minute walk of Buzzy Park and Pettee Memorial Library.
Wilmington Family Escape! King Beds, Sleeps 13, Air hockey, Nerfgun Fun
Amazing lake views & access,HotTub & sauna, quality game Rm.  190-5 star Reviews

Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews

Wilmington
Located in Wilmington, this vacation home is on the waterfront, within a 5-minute walk of Deerfield River and Harriman Reservoir.
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
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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
348 Holiday Homes
Lowest Price
AU$175
Highest Price
AU$271
Popular accommodation
Cozy, charming mountain home., Dog-friendly chalet cabin with valley view, deck, and private hot tub, Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating , Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns, New Chalet mins to Mt with Hot tub, Walk to Ski Lift: Spacious Condo in West Dover!, West Dover Townhome Near Mount Snow Shuttle Stop!, Wilmington Family Escape! King Beds, Sleeps 13, Air hockey, Nerfgun Fun, Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews

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$210 per night from 5 Dec to 6 Dec
AU$210
includes taxes & fees
5 Dec - 6 Dec
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
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
1043 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is AU$175 per night from 10 Nov to 11 Nov
AU$175
includes taxes & fees
10 Nov - 11 Nov
With a stay at The Covered Bridge Inn in Brattleboro, you'll be within a 10-minute walk of Brattleboro Bowl and United States Navy Seabee Bridge.
The Covered Bridge 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$195 per night from 6 Nov to 7 Nov
AU$195
includes taxes & fees
6 Nov - 7 Nov
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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Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
89 Grand Summit Way, West Dover, VT
Fully refundable
The price is AU$271 per night from 6 Nov to 7 Nov
AU$271
includes taxes & fees
6 Nov - 7 Nov
Located in West Dover, Mount Snow Grand Summit Resort is a 1-minute drive from Mount Snow and 8 minutes from Mount Snow Golf Course.
Mount Snow Grand Summit Resort
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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.