Book Holiday Homes in Stockbridge

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Featured Holiday Homes in Stockbridge

New w Views Of K, Sleeps 12-no bunks, Hot Tub, Sauna, 2mi to base 3 bd, 2.5b

New w Views Of K, Sleeps 12-no bunks, Hot Tub, Sauna, 2mi to base 3 bd, 2.5b

Killington
Book a stay at this family-friendly vacation home in Killington. Enjoy a sauna, tennis courts, and patios. Popular attractions Killington Resort and Killington ...
New w Views Of K, Sleeps 12-no bunks, Hot Tub, Sauna, 2mi to base 3 bd, 2.5b
Mountain-view home with deck  - minutes to Okemo Mountain & Skyeship Gondola

Mountain-view home with deck - minutes to Okemo Mountain & Skyeship Gondola

Plymouth
Book a stay at this family-friendly vacation home in Plymouth. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Amherst Lake and Echo ...
Mountain-view home with deck - minutes to Okemo Mountain & Skyeship Gondola
☆ 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
Book a stay at this ski vacation home in Killington. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Killington Resort and Skyeship ...
☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace
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MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!

MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!

Killington
Book a stay at this family-friendly vacation home in Killington. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Killington Resort and Pico ...
MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!
BruinsDen - Ski On Ski Off (Home Stretch Trail)

BruinsDen - Ski On Ski Off (Home Stretch Trail)

Killington
Book a stay at this ski vacation home in Killington. Enjoy free WiFi, a garden, and ski-in/ski-out access. Popular attractions Killington Resort and Skyeship ...
BruinsDen - Ski On Ski Off (Home Stretch Trail)
Dog-friendly cabin with forest setting, woodstove & deck - near Killington

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

Plymouth
Stay at this vacation home in Plymouth. Enjoy patios, in-room washers/dryers, and an in-room coffeemaker. Popular attractions Killington Resort and Sunrise Village ...
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
Spectacular opportunity to enjoy the finest property in Killington Summit

Spectacular opportunity to enjoy the finest property in Killington Summit

Killington
Book a stay at this family-friendly vacation home in Killington. Enjoy free WiFi, a fitness center, and patios. Popular attractions Killington Resort and Pico ...
Spectacular opportunity to enjoy the finest property in Killington Summit
S'Mookie the Bear- ski on and off, hot tub, pool

S'Mookie the Bear- ski on and off, hot tub, pool

Killington
Book a stay at this ski vacation home in Killington. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Killington Resort and Pico Mountain ...
S'Mookie the Bear- ski on and off, hot tub, pool
The Ridge Chalet, an A-Frame Killington home

The Ridge Chalet, an A-Frame Killington home

Killington
Book a stay at this family-friendly vacation home in Killington. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Killington Resort ...
The Ridge Chalet, an A-Frame Killington home
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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
565 Holiday Homes
Lowest Price
NZ$195
Highest Price
NZ$658
Popular accommodation
New w Views Of K, Sleeps 12-no bunks, Hot Tub, Sauna, 2mi to base 3 bd, 2.5b, Mountain-view home with deck - minutes to Okemo Mountain & Skyeship Gondola, ☆ SKI ON & OFF! ☆ Spruce Glen D on Great Eastern Trail w/AC, Sauna, Fireplace, MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!, BruinsDen - Ski On Ski Off (Home Stretch Trail), Dog-friendly cabin with forest setting, woodstove & deck - near Killington, Spectacular opportunity to enjoy the finest property in Killington Summit, S'Mookie the Bear- ski on and off, hot tub, pool, The Ridge Chalet, an A-Frame Killington home

Top trending hotels in Stockbridge

Comfort Inn Trolley Square

Comfort Inn Trolley Square

2.5 out of 5
19 Allen St, Rutland, VT
Fully refundableReserve now, pay when you stay
The price is NZ$195 per night from 8 Dec to 9 Dec
NZ$195
includes taxes & fees
8 Dec - 9 Dec
Book a stay at this business-friendly hotel in Rutland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Comfort Inn Trolley Square
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 NZ$320 per night from 3 Dec to 4 Dec
NZ$320
includes taxes & fees
3 Dec - 4 Dec
Stay at this 3.5-star ski hotel in Killington. Enjoy free WiFi, a free ski shuttle, and a 24-hour fitness center. Our guests praise the helpful staff and the ...
Killington Mountain Lodge, Tapestry Collection by Hilton
Hampton Inn White River Junction

Hampton Inn White River Junction

2.5 out of 5
104 Ballardvale Dr, White River Junction, VT
Fully refundableReserve now, pay when you stay
The price is NZ$223 per night from 1 Dec to 2 Dec
NZ$223
includes taxes & fees
1 Dec - 2 Dec
Book a stay at this business-friendly hotel in White River Junction. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the ...
Hampton Inn White River Junction
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Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is NZ$658 per night from 16 Dec to 17 Dec
NZ$658
includes taxes & fees
16 Dec - 17 Dec
Book a stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
Woodstock Inn & Resort
Don't see what you're looking for?
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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.