Book Holiday Homes in Stockbridge

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Featured Holiday Homes in Stockbridge

Spacious country home, beautiful sunsets, 40 acres

Spacious country home, beautiful sunsets, 40 acres

Tunbridge
This vacation home is 11.5 mi (18.6 km) from Gifford Medical Center and 20.9 mi (33.6 km) from Silver Lake State Park.
Spacious country home, beautiful sunsets, 40 acres
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 ...
Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen
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
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Spectacular 4 Bed Killington Home

Spectacular 4 Bed Killington Home

Killington
When you stay at this vacation home in Killington, you'll be in the mountains, a 2-minute drive from Killington Resort and 8 minutes from Pico Mountain at Killington ...
Spectacular 4 Bed Killington Home
Slopeside Chalet - Ski to and from your home!

Slopeside Chalet - Ski to and from your home!

Killington
The price is AU$1,096 per night from 3 Nov to 4 Nov
AU$1,096
includes taxes & fees
3 Nov - 4 Nov
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 Bear Mountain Quad ...
Slopeside Chalet - Ski to and from your home!
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 within a 5-minute drive of The Strong House Spa.
Spacious 6-bedroom house in charming Quechee. Family friendly, all seasons!
Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated

Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated

Killington
When you stay at this vacation home in Killington, you'll be in the mountains, just steps from Killington Resort and 15 minutes by foot from Sunrise Village ...
Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated
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 Killington Resort and Pico Mountain at Killington Ski ...
Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail
Luxurious guest home with private art gallery in the heart of a historic village

Luxurious guest home with private art gallery in the heart of a historic village

Brandon
With a stay at this vacation home in Brandon, you'll be within a 10-minute walk of Judith Reilly Gallery and Stephen A Douglas Birthplace.
Luxurious guest home with private art gallery in the heart of a historic village
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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
550 Holiday Homes
Lowest Price
AU$186
Highest Price
AU$1,096
Popular accommodation
Spacious country home, beautiful sunsets, 40 acres, Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen, Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge, Spectacular 4 Bed Killington Home, Slopeside Chalet - Ski to and from your home!, Spacious 6-bedroom house in charming Quechee. Family friendly, all seasons! , Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated, Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail, Luxurious guest home with private art gallery in the heart of a historic village

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$221 per night from 3 Nov to 4 Nov
AU$221
includes taxes & fees
3 Nov - 4 Nov
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 ...
White River Inn and Suites
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$243 per night from 19 Nov to 20 Nov
AU$243
includes taxes & fees
19 Nov - 20 Nov
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
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 AU$198 per night from 1 Dec to 2 Dec
AU$198
includes taxes & fees
1 Dec - 2 Dec
With a stay at Hampton Inn White River Junction, you'll be centrally located in White River Junction, within a 10-minute drive of Dartmouth College and Upper ...
Hampton Inn White River Junction
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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 AU$186 per night from 14 Nov to 15 Nov
AU$186
includes taxes & fees
14 Nov - 15 Nov
With a stay at Comfort Inn Trolley Square 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 at ...
Comfort Inn Trolley Square
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.