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Featured Holiday Homes in Shaftsbury

Secluded home with game room, private hot tub, golf, river & mtn views, firepit

Secluded home with game room, private hot tub, golf, river & mtn views, firepit

Manchester
When you a stay at this vacation home in Manchester Center, you'll be next to a golf course, within a 5-minute walk of Green Mountain National Forest and Battenkill ...
Secluded home with game room, private hot tub, golf, river & mtn views, firepit
Peaceful Stay at Birds of a Feather Farm & Spa

Peaceful Stay at Birds of a Feather Farm & Spa

Shaftsbury
The price is AU$418 per night from 13 Apr to 14 Apr
AU$418
includes taxes & fees
13 Apr - 14 Apr
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
Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer

Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer

Stratton
When you stay at this vacation home in Stratton, you'll be in the mountains, within a 10-minute walk of Stratton Mountain Resort and Green Mountain National ...
Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer
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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
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

Dorset
With a stay at this vacation home in Rupert, you'll be on a river, just steps from Green Mountain National Forest and a 4-minute drive from Dorset Historical ...
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style
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
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!
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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.

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

Holiday houses in Shaftsbury 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 Shaftsbury 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 Shaftsbury adventures, obvs.

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

Shaftsbury Holiday Homes essential information

Accommodation
771 Holiday Homes
Lowest Price
AU$280
Highest Price
AU$418
Popular accommodation
Secluded home with game room, private hot tub, golf, river & mtn views, firepit, Peaceful Stay at Birds of a Feather Farm & Spa , Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer, Cozy Converted Barn on Secluded 6.5 acres with Hot Tub, Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style, 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!

Top trending hotels in Shaftsbury

Peaceful Stay at Birds of a Feather Farm & Spa

Peaceful Stay at Birds of a Feather Farm & Spa

Shaftsbury
The price is AU$418 per night from 13 Apr to 14 Apr
AU$418
includes taxes & fees
13 Apr - 14 Apr
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
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
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
The price is AU$389 per night from 3 Apr to 4 Apr
AU$389
includes taxes & fees
3 Apr - 4 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
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The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
3567 Main Street Route 7A, Manchester, VT
Fully refundableReserve now, pay when you stay
The price is AU$280 per night from 3 Apr to 4 Apr
AU$280
includes taxes & fees
3 Apr - 4 Apr
When you a stay at The Equinox Golf Resort & Spa in Manchester, you'll be in the mountains, just steps from Green Mountain National Forest and Golf Club at ...
The Equinox Golf Resort & 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.