Holiday Homes in Stockbridge

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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 €460
includes taxes & fees
19 Apr - 20 Apr
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 €460
includes taxes & fees
19 Apr - 20 Apr
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, (42 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 €165
includes taxes & fees
26 Apr - 27 Apr
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 €207
includes taxes & fees
23 Apr - 24 Apr
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

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 €467
includes taxes & fees
19 Apr - 20 Apr
Large Killington Area Home | Sleeps 7 | Game Room

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)
"Wonderful cabin, well stocked, host was attentive and quick to address any questions."
United States
Eyal O.
The price is €412
includes taxes & fees
19 Apr - 20 Apr
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

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 €553
includes taxes & fees
26 Apr - 27 Apr
The Tower House | Hot Tub | Firepit | Dog-Friendly

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 €232
includes taxes & fees
21 Apr - 22 Apr
CozyDen - AC, Grill, Bike to Mountain, Porch!

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 €675
includes taxes & fees
19 Apr - 20 Apr
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!

Feel the real VT! Ski Killington and a foodie’s delight!

Feel the real VT! Ski Killington and a foodie’s 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 €479
includes taxes & fees
11 May - 12 May
Feel the real VT! Ski Killington and a foodie’s delight!

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)
"Great location and excellent hosts "
United States
Peter G.
The price is €559
includes taxes & fees
26 Apr - 27 Apr
The Big Lebearski- AC, Grill, Fire Pit, Hot tub!

Vermont Retreat: 3BR with Mountain Views and Trails

Vermont Retreat: 3BR with Mountain Views and Trails
Brookfield
The price is €510
includes taxes & fees
26 Apr - 27 Apr
Vermont Retreat: 3BR with Mountain Views and Trails

Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley
Warren
9.6 out of 10, Exceptional, (43 reviews)
"Very convenient to Warren center. This house served us well as we were able to bring our dog over the Christmas holiday. Perfect house for a family. "
United States
Monica R.
Beautiful home located in the Mad River Valley

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 €359
includes taxes & fees
26 Apr - 27 Apr
The Grizz- AC, Pool, Sauna, Gym, Near Resort

Walk to Pickle Barrel & Jax. Hot tub & Views

Walk to Pickle Barrel & Jax. Hot tub & Views
Killington
10.0 out of 10, Exceptional, (7 reviews)
"Great hosts with a great location to Killington"
United States
Ed P.
The price is €455
includes taxes & fees
25 Apr - 26 Apr
Walk to Pickle Barrel & Jax. Hot tub & Views

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 €365
includes taxes & fees
26 Apr - 27 Apr
Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown

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 €399
includes taxes & fees
23 Apr - 24 Apr
large ski ranch hot tub close to killington pets ok

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 €546
includes taxes & fees
26 Apr - 27 Apr
Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna

180-degree panoramic views of Vermont's mountains from the living room and Deck

180-degree panoramic views of Vermont's mountains from the living room and Deck
Hartford
8.0 out of 10, Very good, (2 reviews)
"The house was absolutely beautiful. A unique mix of modern and 70’s. The layout was spot on . We were only there one night , a very quick stop over but it was so comfortable and cozy. The host was so easy to communicate with and was very accommodating. Plenty of room to sleep a large group and the views….you have to see in person. Stunning . I travel a lot and use VRBO for all of my travels. This was one of the best experiences I have had . I recommend 100%. "
United States
Mary Anne C.
The price is €464
includes taxes & fees
19 Apr - 20 Apr
180-degree panoramic views of Vermont's mountains from the living room and Deck

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 €752
includes taxes & fees
20 Apr - 21 Apr
Royalbear-AC, Hot Tub, Grill, FirePit, Gameroom
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
209
Accommodation
669 Holiday Homes
Lowest Price
€165
Highest Price
€752