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.
Opens in a new windowBeautifully 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$293 per night from 24 Sept to 25 Sept
AU$293
24 Sept - 25 Sept
includes taxes & fees
Located in Chelsea, this vacation home is within a 5-minute drive of Alden Speare Memorial Library and Chelsea Public Library.
Opens in a new windowBarn stay with dairy goats! Your clean cozy spot in the barn is waiting for you
Idyllic Lakefront House Suited Two  Families

Idyllic Lakefront House Suited Two Families

Ludlow
With a stay at this vacation home in Ludlow, you'll be on the waterfront, within a 10-minute drive of Okemo Mountain Resort and Green Mountain Sugar House.
Opens in a new windowIdyllic Lakefront House Suited Two Families
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Dog-friendly house w/ deck, EV charger, fireplace, partial a/c, BBQ, w/d, wifi

Dog-friendly house w/ deck, EV charger, fireplace, partial a/c, BBQ, w/d, wifi

Plymouth
Located in Plymouth, this vacation home is in the mountains, within a 15-minute drive of Long Trail Brewing Company and Coolidge State Park.
Opens in a new windowDog-friendly house w/ deck, EV charger, fireplace, partial a/c, BBQ, w/d, wifi
Quiet Modern Luxury Home w/  Memory Foam Beds, A/C, FAST WiFi and Full Kitchen

Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen

Bridgewater
With a stay at this vacation home in Bridgewater Corners, you'll be on a river, within a 15-minute drive of Killington Resort and Long Trail Brewing ...
Opens in a new windowQuiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen
Ski house 8 min from the mountain

Ski house 8 min from the mountain

Killington
With a stay at this vacation home in Killington, you'll be within a 15-minute drive of Killington Resort and Green Mountain National Forest.
Opens in a new windowSki house 8 min from the mountain
Dog-friendly cabin with forest setting, woodstove & deck - near Killington

Dog-friendly cabin with forest setting, woodstove & deck - near Killington

Plymouth
With a stay at this vacation home in Plymouth, you'll be within a 10-minute drive of Skyeship Express Gondola Stage I and Calvin Coolidge Homestead.
Opens in a new windowDog-friendly cabin with forest setting, woodstove & deck - near Killington
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 5-minute drive of Killington Resort and Skyeship Express Gondola Stage I.
Opens in a new windowPrivate, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
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.
Opens in a new windowLake front house about 1 mile from Okemo's Jackson Gore Base Lodge
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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
777 Holiday Homes
Lowest Price
AU$140
Highest Price
AU$1,056
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, Idyllic Lakefront House Suited Two Families, Dog-friendly house w/ deck, EV charger, fireplace, partial a/c, BBQ, w/d, wifi, Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen, Ski house 8 min from the mountain, Dog-friendly cabin with forest setting, woodstove & deck - near Killington, Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi, Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

Top trending hotels in Stockbridge

White River Inn and Suites

White River Inn and Suites

2.5 out of 5
91 Ballardvale Drive, White River Junction, VT
Fully refundableReserve now, pay when you stay
The price is AU$193 per night from 19 Oct to 20 Oct
AU$193
19 Oct - 20 Oct
includes taxes & fees
Located in White River Junction, White River Inn and Suites is in a rural location, just a 3-minute walk from Upper Valley Aquatic Center and a 3-minute drive ...
Opens in a new windowWhite River Inn and Suites
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
Fully refundableReserve now, pay when you stay
Located in Woodstock, The Shire Woodstock is on a river, within a 5-minute walk of Mt Ascutney Hospital and Health Center Primary Care - Woodstock and Ottauquechee ...
Opens in a new windowThe Shire Woodstock
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is AU$1,056 per night from 21 Sept to 22 Sept
AU$1,056
21 Sept - 22 Sept
includes taxes & fees
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 ...
Opens in a new windowWoodstock Inn & Resort
Save an average of 15% on thousands of hotels when you're signed in
Super 8 by Wyndham White River Junction

Super 8 by Wyndham White River Junction

2 out of 5
442 North Hartland Rd, I-91 Exit 11 Rt 5 S 1/4 Mile, White River Junction, VT
Fully refundableReserve now, pay when you stay
The price is AU$140 per night from 19 Oct to 20 Oct
AU$140
19 Oct - 20 Oct
includes taxes & fees
With a stay at Super 8 by Wyndham White River Junction in White River Junction, you'll be within a 10-minute drive of Dartmouth College and Upper Valley Aquatic ...
Opens in a new windowSuper 8 by Wyndham White River Junction
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.