Book Holiday Homes in West Chesterfield

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Featured Holiday Homes in West Chesterfield

Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC

Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC

Townshend, VT
Located in Townshend, this vacation home is in the mountains, within a 15-minute drive of West River and Newfane Town Hall.
Opens in a new windowLuxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC
The Jelly Mill-A Peaceful River Retreat

The Jelly Mill-A Peaceful 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.
Opens in a new windowThe Jelly Mill-A Peaceful River Retreat
Beautiful Modern A-Frame in Southern Vermont is The Place To BE!

Beautiful Modern A-Frame in Southern Vermont is The Place To BE!

Whitingham
When you stay at this vacation home in Whitingham, you'll be within a 10-minute drive of Harriman Reservoir and Rowe State Forest.
Opens in a new windowBeautiful Modern A-Frame in Southern Vermont is The Place To BE!
Save an average of 15% on thousands of hotels when you're signed in
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.
Opens in a new windowBrand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.
Beautiful Custom Built Timber Frame Home, Sleeps 11

Beautiful Custom Built Timber Frame Home, Sleeps 11

Wilmington
Located in Wilmington, this vacation home is on a lake, a 1-minute drive from Lake Raponda and 9 minutes from South Main Street.
Opens in a new windowBeautiful Custom Built Timber Frame Home, Sleeps 11
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.
Opens in a new windowAmazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
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 Forest.
Opens in a new windowModern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns
Walk to Ski Lifts with Perfect Location! 3 Bedroom Townhome plus Loft.

Walk to Ski Lifts with Perfect Location! 3 Bedroom Townhome plus Loft.

Dover
When you stay at this vacation home in West Dover, you'll be next to a golf course, within a 15-minute walk of Mount Snow and Green Mountain National ...
Opens in a new windowWalk to Ski Lifts with Perfect Location! 3 Bedroom Townhome plus Loft.
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.
Opens in a new windowFantastic 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
371 Holiday Homes
Lowest Price
AU$160
Highest Price
AU$252
Popular accommodation
Luxurious, stunning views, private setting, pet friendly, firepit ,EV, WIFI, AC, The Jelly Mill-A Peaceful River Retreat, Beautiful Modern A-Frame in Southern Vermont is The Place To BE!, Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit. , Beautiful Custom Built Timber Frame Home, Sleeps 11, Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews, Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns, Walk to Ski Lifts with Perfect Location! 3 Bedroom Townhome plus Loft., Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!

Top trending hotels in West Chesterfield

Riverside Hotel, an Ascend Collection Hotel

Riverside Hotel, an Ascend Collection Hotel

2.5 out of 5
20 Riverside Drive, West Chesterfield, NH
Fully refundable
The price is AU$252 per night from 24 Nov to 25 Nov
AU$252
24 Nov - 25 Nov
includes taxes & fees
With a stay at Riverside Hotel, an Ascend Collection Hotel in West Chesterfield, you'll be in the historical district, just a 1-minute walk from Connecticut ...
Opens in a new windowRiverside Hotel, an Ascend Collection Hotel
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$160 per night from 6 Nov to 7 Nov
AU$160
6 Nov - 7 Nov
includes taxes & fees
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.
Opens in a new windowThe Covered Bridge Inn
Mountaineer Inn

Mountaineer Inn

2 out of 5
270 Handle Rd, West Dover, VT
Fully refundableReserve now, pay when you stay
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.
Opens in a new windowMountaineer Inn
Save an average of 15% on thousands of hotels when you're signed in
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

2 out of 5
3 Ash Brook Road, Keene, NH
Fully refundableReserve now, pay when you stay
The price is AU$168 per night from 5 Nov to 6 Nov
AU$168
5 Nov - 6 Nov
includes taxes & fees
Located in Keene, Days Inn by Wyndham Keene NH is in a shopping district, within a 5-minute drive of Cheshire Children's Museum and Historical Society of Cheshire ...
Opens in a new windowDays Inn by Wyndham Keene NH
Don't see what you're looking for?
See all available properties in West Chesterfield
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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.