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Featured Holiday Homes in Whitingham

Peaceful Stay at Birds of a Feather Farm & Spa

Peaceful Stay at Birds of a Feather Farm & Spa

Shaftsbury
The price is AU$413 per night from 5 May to 6 May
AU$413
includes taxes & fees
5 May - 6 May
Located in Shaftsbury, this vacation home is a 1-minute drive from Green Mountain National Forest and 6 minutes from Shaftsbury Historical Society Museum.
Peaceful Stay at Birds of a Feather Farm & Spa
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
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub

Cozy Converted Barn on Secluded 6.5 acres with Hot Tub

Shaftsbury
A stay at this vacation home places you in the heart of Shaftsbury, steps from Green Mountain National Forest and 13 minutes by foot from Robert Frost Stone ...
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
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1810 Brook Side Mill/House / EV Level 2 Charging on Site

1810 Brook Side Mill/House / EV Level 2 Charging on Site

Shelburne Falls
Located in Shelburne Falls, this vacation home is in a rural location, within a 5-minute drive of Deerfield River and Bald Mountain Pottery.
1810 Brook Side Mill/House / EV Level 2 Charging on Site
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!
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.

Whitingham 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 Whitingham vacation homes are the perfect way for you to wing it.

Holiday houses in Whitingham 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 Whitingham 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 Whitingham adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Whitingham 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 Whitingham 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.

Whitingham Holiday Homes essential information

Accommodation
494 Holiday Homes
Lowest Price
AU$190
Highest Price
AU$413
Popular accommodation
Peaceful Stay at Birds of a Feather Farm & Spa , The Jelly Mill-A River Retreat, Cozy Converted Barn on Secluded 6.5 acres with Hot Tub, 1810 Brook Side Mill/House / EV Level 2 Charging on Site, Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit. , Cozy retreat near slopes, GAMERS HAVEN, River Wine Inn!, Snow Mountain Lodge- 6 miles from Mt Snow. Ski, Hike, Indoor Pool, Relax!, Wilmington Vacation Rental Near Hiking and Skiing!

Top trending hotels in Whitingham

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
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is AU$390 per night from 27 Apr to 28 Apr
AU$390
includes taxes & fees
27 Apr - 28 Apr
Located in Williamstown, The Williams Inn is just steps from Williams College and 11 minutes by foot from The Clark Art Institute.
The Williams Inn
Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is AU$222 per night from 29 Apr to 30 Apr
AU$222
includes taxes & fees
29 Apr - 30 Apr
A stay at Hotel Downstreet, Ascend Hotel Collection places you in the heart of North Adams, steps from MCLA Gallery 51 and North Adams City Hall.
Hotel Downstreet, Ascend Hotel Collection
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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$190 per night from 4 May to 5 May
AU$190
includes taxes & fees
4 May - 5 May
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.