Book Holiday Homes in West Chesterfield

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Featured Holiday Homes in West Chesterfield

Cozy Home Near Downtown, Shops, and Restaurants.

Cozy Home Near Downtown, Shops, and Restaurants.

2 out of 5
Keene
The price is AU$948 per night from 3 Apr to 4 Apr
AU$948
includes taxes & fees
3 Apr - 4 Apr
Located in Keene, this vacation home is within a 15-minute walk of Ashuelot River and Cheshire Children's Museum.
Cozy Home Near Downtown, Shops, and Restaurants.
The Jelly Mill-A River Retreat

The Jelly Mill-A River Retreat

Guilford
When you stay at this vacation home in Brattleboro, you'll be on the waterfront and 7 minutes by car from Green River Wildlife Management Area.
The Jelly Mill-A River Retreat
Potter's Place | House in Jamaica with mountain views

Potter's Place | House in Jamaica with mountain views

Jamaica
Located in Jamaica, this vacation home is within a 5-minute drive of West River and Green Mountain National Forest.
Potter's Place | House in Jamaica with mountain views
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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.
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
GAMERS HAVEN, River Wine Inn!

GAMERS HAVEN, River Wine Inn!

2 out of 5
Whitingham
Located in Jacksonville, this vacation home is a 1-minute drive from Jacksonville Pond and 6 minutes from Harriman Reservoir.
GAMERS HAVEN, River Wine Inn!
 Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont

Putney
The price is AU$543 per night from 3 Apr to 4 Apr
AU$543
includes taxes & fees
3 Apr - 4 Apr
Located in Putney, this vacation home is on a lake, within a 5-minute drive of Harlow's and Next Stage Arts.
Family Friendly Hilltop House In Putney Vermont
Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Hike, Indoor Pool, Relax!

Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Hike, Indoor Pool, Relax!

Wardsboro
Located in Wardsboro, this vacation home is in the mountains, within a 15-minute drive of Green Mountain National Forest and Wardsboro Public Library.
Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Hike, Indoor Pool, Relax!
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!
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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
412 Holiday Homes
Lowest Price
AU$187
Highest Price
AU$948
Popular accommodation
Cozy Home Near Downtown, Shops, and Restaurants., The Jelly Mill-A River Retreat, Potter's Place | House in Jamaica with mountain views, Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit. , Cozy retreat near slopes, GAMERS HAVEN, River Wine Inn!, Family Friendly Hilltop House In Putney Vermont, Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Hike, Indoor Pool, Relax!, Wilmington Vacation Rental Near Hiking and Skiing!

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 Apr to 7 Apr
AU$248
includes taxes & fees
6 Apr - 7 Apr
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
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$187 per night from 28 Apr to 29 Apr
AU$187
includes taxes & fees
28 Apr - 29 Apr
Located in Brattleboro, Hampton Inn Brattleboro is a 2-minute drive from Brattleboro Bowl and 7 minutes from Brattleboro Farmers' Market.
Hampton Inn Brattleboro
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$195 per night from 3 Apr to 4 Apr
AU$195
includes taxes & fees
3 Apr - 4 Apr
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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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 3 Apr to 4 Apr
AU$191
includes taxes & fees
3 Apr - 4 Apr
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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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.