Book Holiday Homes in Stockbridge

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Featured Holiday Homes in Stockbridge

Killington, Vermont Ski House w/ Hot Tub and Sauna

Killington, Vermont Ski House w/ Hot Tub and Sauna

Killington
When you stay at this vacation home in Killington, you'll be in the mountains, within a 10-minute drive of Pico Mountain at Killington Ski Resort and Killington ...
Killington, Vermont Ski House w/ Hot Tub and Sauna
Walk to Pickle Barrel & Jax. Hot tub & Views

Walk to Pickle Barrel & Jax. Hot tub & Views

2 out of 5
Killington
The price is AU$1,180 per night from 14 Jan to 15 Jan
AU$1,180
includes taxes & fees
14 Jan - 15 Jan 2025
With a stay at this vacation home in Killington, you'll be a 1-minute drive from Killington Resort and 6 minutes from Pico Mountain at Killington Ski ...
Walk to Pickle Barrel & Jax. Hot tub & Views
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.
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
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Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail

Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail

Killington
With a stay at this vacation home in Killington (North Sherburne), you'll be within a 15-minute drive of Pico Mountain at Killington Ski Resort and Killington ...
Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail
Ideal Killington Escape! Hot tub, game room, grill, 2 fireplaces, pet-friendly!

Ideal Killington Escape! Hot tub, game room, grill, 2 fireplaces, pet-friendly!

Killington
When you stay at this vacation home in Killington, you'll be in the mountains, within a 10-minute drive of Killington Resort and Pico Mountain at Killington ...
Ideal Killington Escape! Hot tub, game room, grill, 2 fireplaces, pet-friendly!
BruinsDen - Ski On Ski Off (Home Stretch Trail)

BruinsDen - Ski On Ski Off (Home Stretch Trail)

Killington
The price is AU$1,941 per night from 25 Dec to 26 Dec
AU$1,941
includes taxes & fees
25 Dec - 26 Dec
When you stay at this vacation home in Killington, you'll be in the mountains, just steps from Killington Resort and a 4-minute drive from Skye Peak Express ...
BruinsDen - Ski On Ski Off (Home Stretch Trail)
Spacious 6-bedroom house in charming Quechee. Family friendly, all seasons!

Spacious 6-bedroom house in charming Quechee. Family friendly, all seasons!

2 out of 5
Quechee
With a stay at this vacation home in Quechee, you'll be a 5-minute walk from Quechee Ski Hill and 8 minutes by foot from Maples.
Spacious 6-bedroom house in charming Quechee. Family friendly, all seasons!
Ski-in/out sunrise condo with pool & hot tub - great ski retreat

Ski-in/out sunrise condo with pool & hot tub - great ski retreat

Killington
When you stay at this vacation home in Killington, you'll be in the mountains, just steps from Killington Resort and a 3-minute drive from Sunrise Village Triple ...
Ski-in/out sunrise condo with pool & hot tub - great ski retreat
Relax at Bear Run: A spacious 5-bedroom retreat in Killington, VT, perfect for up to 12 guests

Relax at Bear Run: A spacious 5-bedroom retreat in Killington, VT, perfect for up to 12 guests

Killington
With a stay at this vacation home in Killington, you'll be a 1-minute drive from Killington Resort and 6 minutes from Skyeship Express Gondola Stage II.
Relax at Bear Run: A spacious 5-bedroom retreat in Killington, VT, perfect for up to 12 guests
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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
555 Holiday Homes
Lowest Price
AU$238
Highest Price
AU$1,941
Popular accommodation
Killington, Vermont Ski House w/ Hot Tub and Sauna, Walk to Pickle Barrel & Jax. Hot tub & Views, Dog-friendly cabin with forest setting, woodstove & deck - near Killington, Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail, Ideal Killington Escape! Hot tub, game room, grill, 2 fireplaces, pet-friendly!, BruinsDen - Ski On Ski Off (Home Stretch Trail), Spacious 6-bedroom house in charming Quechee. Family friendly, all seasons! , Ski-in/out sunrise condo with pool & hot tub - great ski retreat, Relax at Bear Run: A spacious 5-bedroom retreat in Killington, VT, perfect for up to 12 guests

Top trending hotels in Stockbridge

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$342 per night from 14 Jan to 15 Jan
AU$342
includes taxes & fees
14 Jan - 15 Jan 2025
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
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 AU$268 per night from 16 Jan to 17 Jan
AU$268
includes taxes & fees
16 Jan - 17 Jan 2025
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
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 AU$282 per night from 8 Jan to 9 Jan
AU$282
includes taxes & fees
8 Jan - 9 Jan 2025
Located in Killington, North Star Lodge and Resort is in the mountains, a 3-minute drive from Killington Resort and 5 minutes from Killington Golf Course.
North Star Lodge and Resort
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Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
401 US-7, Located At The Junction Of Us 4 And Us 7, Rutland, VT
Fully refundableReserve now, pay when you stay
The price is AU$238 per night from 24 Dec to 25 Dec
AU$238
includes taxes & fees
24 Dec - 25 Dec
When you stay at Days Inn by Wyndham Rutland/Killington Area in Rutland, you'll be near ski lifts, within a 5-minute drive of Vermont State Fairgrounds and Rutland ...
Days Inn by Wyndham Rutland/Killington Area
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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.