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Our top choices for Stockbridge vacation 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 ¥22,582
¥94,655 total
includes taxes & fees
May 25 - May 26
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 ¥22,582
¥94,655 total
includes taxes & fees
May 25 - May 26
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, (44 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 ¥17,180
¥22,805 total
includes taxes & fees
May 27 - May 28
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

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)
"We had a wondetful time! Thank you! The hosts were so accommodating and the place is the perfect winter wonderland getaway. "
United States
Gabriele K.
The price is ¥21,442
¥76,492 total
includes taxes & fees
May 24 - May 25
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

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 ¥15,748
¥38,482 total
includes taxes & fees
May 24 - May 25
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 ¥28,589
¥103,917 total
includes taxes & fees
May 21 - May 22
The Tower House | Hot Tub | Firepit | Dog-Friendly

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 ¥30,223
¥87,832 total
includes taxes & fees
May 21 - May 22
Large Killington Area Home | Sleeps 7 | Game Room

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 ¥20,013
¥43,255 total
includes taxes & fees
May 22 - May 23
CozyDen - AC, Grill, Bike to Mountain, Porch!

Beautiful Woodstock Home with Fire Pit, Grill, and Mountain Charm

Beautiful Woodstock Home with Fire Pit, Grill, and Mountain Charm
Woodstock
The price is ¥44,858
¥105,775 total
includes taxes & fees
May 27 - May 28
Beautiful Woodstock Home with Fire Pit, Grill, and Mountain Charm

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 ¥40,184
¥105,174 total
includes taxes & fees
May 21 - May 22
The Big Lebearski- AC, Grill, Fire Pit, Hot tub!

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 ¥32,641
¥126,604 total
includes taxes & fees
May 27 - May 28
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!

Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals
3.0 star property
Killington
The price is ¥30,296
¥120,500 total
includes taxes & fees
May 21 - May 22
Breakaway House by Killington Vacation Rentals

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 ¥33,190
¥97,257 total
includes taxes & fees
Jun 17 - Jun 18
Feel the real VT! Lakes, hikes, a foodies delight!

180-degree panoramic views of Vermont's mountains from the Living room, Hot Tub

180-degree panoramic views of Vermont's mountains from the Living room, Hot Tub
Hartford
8.0 out of 10, Very Good, (3 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 ¥46,130
¥88,077 total
includes taxes & fees
May 25 - May 26
180-degree panoramic views of Vermont's mountains from the Living room, Hot Tub

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 ¥30,351
¥69,446 total
includes taxes & fees
May 21 - May 22
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 ¥42,376
¥93,961 total
includes taxes & fees
May 21 - May 22
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 ¥47,160
¥100,910 total
includes taxes & fees
May 21 - May 22
Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna

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 ¥61,785
¥128,482 total
includes taxes & fees
May 21 - May 22
BearRight- AC, Pool, Hot Tub, Grill, FirePit

Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.

Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.
Killington
7.0 out of 10, Good, (6 reviews)
"Excellent brief stay."
United States
Ron L.
The price is ¥24,460
¥95,509 total
includes taxes & fees
May 21 - May 22
Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.

Cozy Moonship Yurt in the woods

Cozy Moonship Yurt in the woods
West Rutland
The price is ¥31,766
¥59,593 total
includes taxes & fees
Jun 2 - Jun 3
Cozy Moonship Yurt in the woods
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 Vacation Homes information

Number of reviews
154
Accommodation
723 Vacation Homes
Lowest Price
¥22,805
Highest Price
¥128,482