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Our top choices for Stockbridge holiday homes

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 £428
includes taxes & fees
17 May - 18 May
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock

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 £428
includes taxes & fees
17 May - 18 May
Ski Home/Arcade Mountain Views Near Killington/Woodstock

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, (43 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 £110
includes taxes & fees
17 May - 18 May
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

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 £183
includes taxes & fees
24 May - 25 May
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

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 £487
includes taxes & fees
17 May - 18 May
The Tower House | Hot Tub | Firepit | Dog-Friendly

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 £411
includes taxes & fees
19 May - 20 May
Feel the real VT! Lakes, hikes, a foodies delight!

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, (41 reviews)
"Very easy check in and out and clean home. Streets nearby can be hard to travel without 4 wheel drive. "
United States
Andrew O.
The price is £361
includes taxes & fees
19 May - 20 May
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

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 £567
includes taxes & fees
18 May - 19 May
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!

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 £204
includes taxes & fees
20 May - 21 May
CozyDen - AC, Grill, Bike to Mountain, Porch!

Large Killington Area Home | Sleeps 7 | Game Room

Large Killington Area Home | Sleeps 7 | Game Room
Bridgewater
9.6 out of 10, Exceptional, (7 reviews)
"My family enjoyed this house and there was plenty of space for sleeping and for the kids to play. Conveniently located for skiing at Killington."
United States
Owen C.
The price is £410
includes taxes & fees
17 May - 18 May
Large Killington Area Home | Sleeps 7 | Game Room

The Big Lebearski- AC, Grill, Fire Pit, Hot tub!

The Big Lebearski- AC, Grill, Fire Pit, Hot tub!
Killington
10.0 out of 10, Exceptional, (19 reviews)
"A very pleasant stay at this place. Nice furnishings, everything clean, the hot tub was utilized. Would recommend this to any group or family seeking nearby cozy accommodations near the slopes. "
United States
Tom W.
The price is £499
includes taxes & fees
17 May - 18 May
The Big Lebearski- AC, Grill, Fire Pit, Hot tub!

The Grizz- AC, Pool, Sauna, Gym, Near Resort

The Grizz- AC, Pool, Sauna, Gym, Near Resort
Killington
10.0 out of 10, Exceptional, (4 reviews)
"Place was overall great and just as advertised. Beds were awesome including the Murphy bed. Thanks for a wonderful weekend! I would definitely stay again. "
United States
Angela S.
The price is £310
includes taxes & fees
19 May - 20 May
The Grizz- AC, Pool, Sauna, Gym, Near Resort

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

Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown
Rutland
10.0 out of 10, Exceptional, (4 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 £320
includes taxes & fees
17 May - 18 May
Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown

Modern Woodland Escape w Wshr dryer and Large Yard

Modern Woodland Escape w Wshr dryer and Large Yard
Ripton
The price is £265
includes taxes & fees
10 Jun - 11 Jun
Modern Woodland Escape w Wshr dryer and Large Yard

Cozy Moonship Yurt in the woods

Cozy Moonship Yurt in the woods
West Rutland
The price is £279
includes taxes & fees
17 May - 18 May
Cozy Moonship Yurt in the woods

BearRight- AC, Pool, Hot Tub, Grill, FirePit

BearRight- AC, Pool, Hot Tub, Grill, FirePit
Killington
9.8 out of 10, Exceptional, (12 reviews)
"Excellent stay, very accommodating hosts. Well organized"
United States
Brian S.
The price is £601
includes taxes & fees
17 May - 18 May
BearRight- AC, Pool, Hot Tub, Grill, FirePit

Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna

Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna
The Woods
10.0 out of 10, Exceptional, (7 reviews)
"Location/proximity to Killington is awesome! A few minutes drive from the parkland lot at Ramshead. The community kept the roads and parking lots plowed well. Communication from the host was excellent. The condo was very comfortable for our family of 3 (2 adults and 4 yr old) and exactly as described. Great spot to relax after our days skiing! We would definitely come back!"
United States
Elizabeth C.
The price is £473
includes taxes & fees
17 May - 18 May
Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna

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 £433
includes taxes & fees
18 May - 19 May
large ski ranch hot tub close to killington pets ok

Royalbear-AC, Hot Tub, Grill, FirePit, Gameroom

Royalbear-AC, Hot Tub, Grill, FirePit, Gameroom
Killington
10.0 out of 10, Exceptional, (24 reviews)
"Great house and location, and responsive hosts. Loved it, def will stay again."
United States
Max P.
The price is £660
includes taxes & fees
18 May - 19 May
Royalbear-AC, Hot Tub, Grill, FirePit, Gameroom

Alpine Chalet Grill, Fire pit, Pool, Gym, CornHole

Alpine Chalet Grill, Fire pit, Pool, Gym, CornHole
Killington
10.0 out of 10, Exceptional, (6 reviews)
"Such a great spot."
United States
Kathleen G.
The price is £667
includes taxes & fees
17 May - 18 May
Alpine Chalet Grill, Fire pit, Pool, Gym, CornHole
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

Find out more about Stockbridge

Stockbridge Holiday Homes information

Number of reviews
178
Accommodation
718 Holiday Homes
Lowest Price
£110
Highest Price
£667