Book Holiday Homes in Stockbridge

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Featured Holiday Homes in Stockbridge

Beautifully renovated with fireplace and coffee bar

Beautifully renovated with fireplace and coffee bar

Hartford
Located in White River Junction, this vacation home is on a river, within a 15-minute walk of The Strong House Spa and Route 4 Glassblowing Studio.
Beautifully renovated with fireplace and coffee bar
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

2 out of 5
Chelsea
The price is AU$253 per night from 2 Apr to 3 Apr
AU$253
includes taxes & fees
2 Apr - 3 Apr
Located in Chelsea, this vacation home is within a 5-minute drive of Alden Speare Memorial Library and Chelsea Public Library.
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

Killington
With a stay at this vacation home in Killington, you'll be within a 15-minute drive of Killington Resort and Pico Mountain at Killington Ski Resort.
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
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Dog-friendly townhome with views, AC & fireplace - walk to Village of Quechee

Dog-friendly townhome with views, AC & fireplace - walk to Village of Quechee

Quechee
When you stay at this vacation home in Quechee, you'll be in the mountains, within a 5-minute drive of The Strong House Spa and Route 4 Glassblowing Studio.
Dog-friendly townhome with views, AC & fireplace - walk to Village of Quechee
Our Quechee Escape: Spacious 5 - bedroom home in breathtaking central Vermont

Our Quechee Escape: Spacious 5 - bedroom home in breathtaking central Vermont

Hartford
Located in White River Junction, this vacation home is a 1-minute drive from Quechee Ski Hill and 5 minutes from Maples.
Our Quechee Escape: Spacious 5 - bedroom home in breathtaking central Vermont
Spacious country home, beautiful sunsets, 40 acres

Spacious country home, beautiful sunsets, 40 acres

Tunbridge
The price is AU$731 per night from 2 Apr to 3 Apr
AU$731
includes taxes & fees
2 Apr - 3 Apr
This vacation home is 4.7 mi (7.5 km) from East Hill and 5.1 mi (8.1 km) from Tunbridge Public Library.
Spacious country home, beautiful sunsets, 40 acres
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

Ludlow
With a stay at this vacation home in Ludlow, you'll be on the waterfront, within a 5-minute drive of Okemo Mountain Resort and Green Mountain Sugar House.
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace

☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace

Killington
When you stay at this vacation home in Killington, you'll be in the mountains, within a 15-minute drive of Killington Resort and Pico Mountain at Killington ...
☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace
Dog-friendly house with picturesque mountain view & near skiing - close to Okemo

Dog-friendly house with picturesque mountain view & near skiing - close to Okemo

Mount Holly
Located in Belmont, this vacation home is in the mountains, within a 10-minute drive of Green Mountain National Forest and Shrewsbury Free Library.
Dog-friendly house with picturesque mountain view & near skiing - close to Okemo
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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.

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

Holiday houses in Stockbridge 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 Stockbridge 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 Stockbridge adventures, obvs.

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

Stockbridge Holiday Homes essential information

Accommodation
727 Holiday Homes
Lowest Price
AU$190
Highest Price
AU$731
Popular accommodation
Beautifully renovated with fireplace and coffee bar, Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you, Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi, Dog-friendly townhome with views, AC & fireplace - walk to Village of Quechee, Our Quechee Escape: Spacious 5 - bedroom home in breathtaking central Vermont, Spacious country home, beautiful sunsets, 40 acres, Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge, ☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace, Dog-friendly house with picturesque mountain view & near skiing - close to Okemo

Top trending hotels in Stockbridge

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
19 Allen St, Rutland, VT
The price is AU$219 per night from 2 Apr to 3 Apr
AU$219
includes taxes & fees
2 Apr - 3 Apr
With a stay at Comfort Inn Rutland - Killington in Rutland, you'll be 0.6 mi (1 km) from Rutland Regional Medical Center and 9.8 mi (15.7 km) from Pico Mountain ...
Comfort Inn Rutland - Killington
Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd, Quechee, VT
Fully refundableReserve now, pay when you stay
The price is AU$190 per night from 14 Apr to 15 Apr
AU$190
includes taxes & fees
14 Apr - 15 Apr
With a stay at Align Inn Vermont in Quechee, you'll be in a state park, within a 15-minute drive of Dartmouth College and Quechee Gorge Village.
Align Inn Vermont
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd, Killington, VT
Fully refundableReserve now, pay when you stay
The price is AU$231 per night from 28 Apr to 29 Apr
AU$231
includes taxes & fees
28 Apr - 29 Apr
With a stay at Killington Mountain Lodge, Tapestry Collection by Hilton in Killington, you'll be next to a golf course, just steps from Killington Resort and ...
Killington Mountain Lodge, Tapestry Collection by Hilton
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Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is AU$593 per night from 6 Apr to 7 Apr
AU$593
includes taxes & fees
6 Apr - 7 Apr
A stay at Woodstock Inn & Resort places you in the heart of Woodstock, a 1-minute drive from Billings Farm and Museum and 7 minutes from Saskadena Six Ski ...
Woodstock Inn & Resort
Don't see what you're looking for?
See all available properties in Stockbridge
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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.