A snowy ski slope with skiers, a cabin, and a mountain range in the background.

Holiday Homes in Stockbridge

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Check prices for these dates

In two weeks
10 July - 12 July
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

Our top choices for Stockbridge holiday homes

Exterior

Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock

Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Stockbridge
10.0 out of 10, Exceptional, (3 reviews)
"Exactly as pictured, specious, clean. Owners were extremely responsive and kind."
United States
Sophie L.
The price is AU$1,023
includes taxes & fees
5 July - 6 July
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Interior

Ski Home/Arcade Mountain Views Near Killington/Woodstock

Ski Home/Arcade Mountain Views Near Killington/Woodstock
Stockbridge
10.0 out of 10, Exceptional, (3 reviews)
"Skied Killington for 2 days and was a 20 min drive. Fun to drive the 100."
United States
Kevin M.
The price is AU$1,009
includes taxes & fees
9 July - 10 July
Ski Home/Arcade Mountain Views Near Killington/Woodstock
Exterior

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
Chelsea
10.0 out of 10, Exceptional, (48 reviews)
"Everything was wonderful and both hosts are very inviting owners friendly always there if you needed anything we can't wait to go back loved it "
United States
Susan K.
The price is AU$211
includes taxes & fees
29 June - 30 June
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you
Private kitchen

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Mendon
9.8 out of 10, Exceptional, (6 reviews)
"Very pretty property, wish we could have spent more time there. Getting in and out was easy and there were plenty of options for food in town just a few minutes away. Great stay."
United States
Aurore H.
The price is AU$333
includes taxes & fees
9 July - 10 July
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Smart TV, fireplace, video games, books

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Mt Holly
9.8 out of 10, Exceptional, (42 reviews)
"This house has great hang out space and plenty of space for a big family!"
United States
Cheri V.
The price is AU$712
includes taxes & fees
29 June - 30 June
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Exterior

Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!

Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
Mount Holly
10.0 out of 10, Exceptional, (11 reviews)
"We had a great time in this beautiful house for a family ski trip. It is located right off the main highway and 8min drive away from Okemo. It has all the amenities we wanted- including hot tub, cozy underground family entertainment room and parking garage. Heidi, the host was super prompt and all instructions about the house were very thorough. "
United States
Chi L.
The price is AU$1,092
includes taxes & fees
29 June - 30 June
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
Fridge, microwave, oven, stovetop

Feel the real VT! Lakes, hikes, a foodies delight!

Feel the real VT! Lakes, hikes, a foodies delight!
Proctor
10.0 out of 10, Exceptional, (1 review)
"Clean and comfortable home. Plenty of space for our family! Great quiet neighborhood made it easy to relax on our trip."
United States
Rebecca
The price is AU$839
includes taxes & fees
30 June - 1 July
Feel the real VT! Lakes, hikes, a foodies delight!
Dining

large ski ranch hot tub close to killington pets ok

large ski ranch hot tub close to killington pets ok
Mendon
9.6 out of 10, Exceptional, (4 reviews)
"The hot tub was great after a day of skiing."
United States
Callison A.
The price is AU$613
includes taxes & fees
9 July - 10 July
large ski ranch hot tub close to killington pets ok
Smart TV, books

Cozy Moonship Yurt in the woods

Cozy Moonship Yurt in the woods
West Rutland
10.0 out of 10, Exceptional, (1 review)
"Clean and cozy with a working hot tub. Would highly recommend"
United States
Justin E.
The price is AU$539
includes taxes & fees
6 July - 7 July
Cozy Moonship Yurt in the woods
Interior

Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown

Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown
Rutland
10.0 out of 10, Exceptional, (5 reviews)
"House was clean, organized and spacious. Great location as well, close to grocery, gas and restaurants. Host answered questions quickly. "
United States
Dominic C.
The price is AU$662
includes taxes & fees
7 July - 8 July
Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown
Interior

CozyDen - AC, Grill, Bike to Mountain, Porch!

CozyDen - AC, Grill, Bike to Mountain, Porch!
Killington
9.0 out of 10, Wonderful, (2 reviews)
"Place was clean and location was great"
United States
Berni H.
The price is AU$390
includes taxes & fees
29 June - 30 June
CozyDen - AC, Grill, Bike to Mountain, Porch!
Property grounds

Modern Farm House…minutes to Okemo; 2 King beds!

Modern Farm House…minutes to Okemo; 2 King beds!
Mount Holly
9.6 out of 10, Exceptional, (19 reviews)
"Fantastic house! Christine was easy to communicate with and made us and our dogs feel incredibly welcome. Looking forward to staying there again."
United States
Rachel L.
The price is AU$714
includes taxes & fees
19 July - 20 July
Modern Farm House…minutes to Okemo; 2 King beds!
House, 6 Bedrooms | Living area

Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals
3.0 star property
Killington
The price is AU$1,032
includes taxes & fees
30 June - 1 July
Breakaway House by Killington Vacation Rentals
TV

Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
North Sherburne
10.0 out of 10, Exceptional, (1 review)
"Peak Hill, is a lovely and very clean home, with a fully stocked kitchen and comfy beds. This home is exactly as the pictures that are shown. We had a very small issue with the door lock (battery), called and it was fixed right away, wonderful service. The owner, Geri, we had the opportunity to meet and she is very kind and a pleasure to speak with. We travel alot and l bring pretty much my own kitchen, pillow...... with me where ever l go. However, l would of been fine using all at this...
United States
Essa R.
The price is AU$913
includes taxes & fees
29 June - 30 June
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
TV, offices

The Tower House | Hot Tub | Firepit | Dog-Friendly

The Tower House | Hot Tub | Firepit | Dog-Friendly
Killington
9.0 out of 10, Wonderful, (2 reviews)
"Great place, near everything and great customer service!!"
United States
Patrick B.
The price is AU$995
includes taxes & fees
30 June - 1 July
The Tower House | Hot Tub | Firepit | Dog-Friendly
TV, fireplace

Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
Bridgewater
8.8 out of 10, Excellent, (3 reviews)
"Great place for a ski weekend"
United States
Kathryn F.
The price is AU$1,012
includes taxes & fees
29 June - 30 June
Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
TV, fireplace, video games, table football

25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.

25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.
Killington
9.6 out of 10, Exceptional, (69 reviews)
"Great stay. Killer location!"
United States
Matthew P.
The price is AU$1,106
includes taxes & fees
1 July - 2 July
25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.
TV, fireplace, Netflix, table football

Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.

Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.
Killington
9.8 out of 10, Exceptional, (56 reviews)
"Perfect for a large group or a couple of families."
United States
Mark B.
The price is AU$1,053
includes taxes & fees
30 June - 1 July
Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.
Smart TV

Family and friend friendly upper ski cabin with bunks, sleeps 8

Family and friend friendly upper ski cabin with bunks, sleeps 8
Killington
Family and friend friendly upper ski cabin with bunks, sleeps 8
6 bedrooms, desk, iron/ironing board, travel cot

DoubleDen- AC, Hot Tub, Fire pit, Grill, Game Room

DoubleDen- AC, Hot Tub, Fire pit, Grill, Game Room
Killington
10.0 out of 10, Exceptional, (26 reviews)
"Had a ski weekend with old friends and Double Den was the perfect spot with plenty of room, close to the ski lodges, enjoyable activities between the game room and the hot tub, and very attentive hosts. Would recommend to anyone looking to get away for a long weekend or an entire week"
United States
Paul D.
The price is AU$1,437
includes taxes & fees
29 June - 30 June
DoubleDen- AC, Hot Tub, Fire pit, Grill, Game Room
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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Top Stockbridge Hotel Reviews

Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent
"Although I only stayed for one night to attend a wedding nearby, I wish I could have spent more time there.the room was excellent - best nights sleep I’ve had in awhile :-)"
William 1-night trip
Posted 1 hour ago
Jackson Gore Village, A Vail Resorts Property

Find out more about Stockbridge

Stockbridge Holiday Homes information

Number of reviews
261
Accommodation
710 Holiday Homes
Lowest Price
AU$211
Highest Price
AU$1,437