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
Book a stay at this golf vacation home in White River Junction. Enjoy free WiFi, a fitness center, and a garden. Popular attractions The Strong House Spa and ...
Beautifully renovated with fireplace and coffee bar
Valley View Retreat is a tastefully decorated home.

Valley View Retreat is a tastefully decorated home.

Killington
Stay at this vacation home in Killington. Enjoy an in-room coffeemaker and in-room fireplaces. Popular attractions Killington Resort and Pico Mountain at Killington ...
Valley View Retreat is a tastefully decorated home.
Walk to Pickle Barrel & Jax. Hot tub & Views

Walk to Pickle Barrel & Jax. Hot tub & Views

2 out of 5
Killington
Stay at this vacation home in Killington. Enjoy a garden, balconies, and an in-room coffeemaker. Popular attractions Killington Resort and Pico Mountain at Killington ...
Walk to Pickle Barrel & Jax. Hot tub & Views
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Killington, Vermont Ski House w/ Hot Tub and Sauna

Killington, Vermont Ski House w/ Hot Tub and Sauna

Killington
Stay at this vacation home in Killington. Enjoy a sauna, patios, and cable/satellite TV service. Popular attractions Killington Resort and Pico Mountain at Killington ...
Killington, Vermont Ski House w/ Hot Tub and Sauna
BruinsDen - Ski On Ski Off (Home Stretch Trail)

BruinsDen - Ski On Ski Off (Home Stretch Trail)

Killington
The price is NZ$2,590 per night from 2 Feb to 3 Feb
NZ$2,590
includes taxes & fees
2 Feb - 3 Feb
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 Pico Mountain ...
BruinsDen - Ski On Ski Off (Home Stretch Trail)
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
Stay at this vacation home in Killington. Enjoy patios, an in-room coffeemaker, and in-room fireplaces. Popular attractions Killington Resort and Pico Mountain ...
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
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
Country townhome - mountain view - walk to Village of Quechee - near Club & golf

Country townhome - mountain view - walk to Village of Quechee - near Club & golf

White River Junction
Stay at this vacation home in White River Junction. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions The Strong House ...
Country townhome - mountain view - walk to Village of Quechee - near Club & golf
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!
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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
547 Holiday Homes
Lowest Price
NZ$214
Highest Price
NZ$2,590
Popular accommodation
Beautifully renovated with fireplace and coffee bar, Valley View Retreat is a tastefully decorated home., Walk to Pickle Barrel & Jax. Hot tub & Views, Killington, Vermont Ski House w/ Hot Tub and Sauna, BruinsDen - Ski On Ski Off (Home Stretch Trail), Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi, Dog-friendly cabin with forest setting, woodstove & deck - near Killington, Country townhome - mountain view - walk to Village of Quechee - near Club & golf, MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!

Top trending hotels in Stockbridge

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
19 Allen St, Rutland, VT
Fully refundableReserve now, pay when you stay
The price is NZ$265 per night from 14 Jan to 15 Jan
NZ$265
includes taxes & fees
14 Jan - 15 Jan
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 Rutland - Killington
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$425 per night from 15 Jan to 16 Jan
NZ$425
includes taxes & fees
15 Jan - 16 Jan
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
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 NZ$214 per night from 26 Jan to 27 Jan
NZ$214
includes taxes & fees
26 Jan - 27 Jan
Book a stay at this business-friendly hotel in Quechee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Align Inn Vermont
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North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
78 Weathervane Dr, Killington, VT
Fully refundableReserve now, pay when you stay
The price is NZ$317 per night from 20 Jan to 21 Jan
NZ$317
includes taxes & fees
20 Jan - 21 Jan
Book a stay at this family-friendly hotel in Killington. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the pool and the helpful staff ...
North Star Lodge and 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.

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