Book Holiday Homes in West Chesterfield

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Featured Holiday Homes in West Chesterfield

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
Primely Located Dover Escape < 1 Mi to Mt Snow!

Primely Located Dover Escape < 1 Mi to Mt Snow!

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.
Primely Located Dover Escape < 1 Mi to Mt Snow!
Fabulous Mountain Top Retreat - 10 minutes from mount snow!

Fabulous Mountain Top Retreat - 10 minutes from mount snow!

Dover
Located in East Dover, this vacation home is within a 15-minute drive of Green Mountain National Forest and North Branch Deerfield River.
Fabulous Mountain Top Retreat - 10 minutes from mount snow!
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Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

Wardsboro
With a stay at this vacation home in Wardsboro, you'll be next to a golf course, within a 15-minute drive of Mount Snow and Green Mountain National Forest.
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!

SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!

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.
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
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
Walk to Mt. Snow! Hot tub! Sauna! Sleeps 16

Walk to Mt. Snow! Hot tub! Sauna! Sleeps 16

West Dover Vermont
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 Mt. Snow! Hot tub! Sauna! Sleeps 16
Beautiful 4 Bedroom Townhome Minutes from Mt Snow

Beautiful 4 Bedroom Townhome Minutes from Mt Snow

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.
Beautiful 4 Bedroom Townhome Minutes from Mt Snow
Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!

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

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.
Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!
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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
352 Holiday Homes
Lowest Price
AU$163
Highest Price
AU$303
Popular accommodation
Dog-friendly chalet cabin with valley view, deck, and private hot tub, Primely Located Dover Escape < 1 Mi to Mt Snow!, Fabulous Mountain Top Retreat - 10 minutes from mount snow!, Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms, SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW! , Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating , Walk to Mt. Snow! Hot tub! Sauna! Sleeps 16, Beautiful 4 Bedroom Townhome Minutes from Mt Snow, Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!

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$249 per night from 2 Jan to 3 Jan
AU$249
includes taxes & fees
2 Jan - 3 Jan 2025
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$303 per night from 5 Jan to 6 Jan
AU$303
includes taxes & fees
5 Jan - 6 Jan 2025
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$172 per night from 1 Jan to 2 Jan
AU$172
includes taxes & fees
1 Jan - 2 Jan 2025
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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Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is AU$163 per night from 12 Jan to 13 Jan
AU$163
includes taxes & fees
12 Jan - 13 Jan 2025
Located in Brattleboro, Hampton Inn Brattleboro is a 2-minute drive from Brattleboro Bowl and 7 minutes from Brattleboro Farmers' Market.
Hampton Inn Brattleboro
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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.