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Check prices for these dates

In two weeks
5 Jun - 7 Jun
In two months
17 Jul - 19 Jul
In three months
14 Aug - 16 Aug
In four months
11 Sept - 13 Sept

Our top choices for Stockbridge holiday homes

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 HK$834
HK$4,269 total
includes taxes & fees
19 May - 20 May
Ski Home/Arcade Mountain Views Near Killington/Woodstock
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 HK$1,042
HK$4,538 total
includes taxes & fees
20 May - 21 May
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Property grounds

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 HK$846
HK$1,123 total
includes taxes & fees
19 May - 20 May
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you
Living area

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 HK$775
HK$1,894 total
includes taxes & fees
24 May - 25 May
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
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 HK$1,410
HK$5,123 total
includes taxes & fees
19 May - 20 May
The Tower House | Hot Tub | Firepit | Dog-Friendly
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 HK$987
HK$2,133 total
includes taxes & fees
19 May - 20 May
CozyDen - AC, Grill, Bike to Mountain, Porch!
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, (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 HK$1,057
HK$3,771 total
includes taxes & fees
19 May - 20 May
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
TV, fireplace, table football, offices

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 HK$1,488
HK$4,324 total
includes taxes & fees
19 May - 20 May
Large Killington Area Home | Sleeps 7 | Game Room
Smart TV, fireplace, video games, stereo

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 HK$1,981
HK$5,185 total
includes taxes & fees
19 May - 20 May
The Big Lebearski- AC, Grill, Fire Pit, Hot tub!
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 HK$1,542
HK$4,666 total
includes taxes & fees
17 Jun - 18 Jun
Feel the real VT! Lakes, hikes, a foodies delight!
Exterior

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

Beautiful Woodstock Home with Fire Pit, Grill, and Mountain Charm
Woodstock
The price is HK$2,114
HK$5,080 total
includes taxes & fees
20 May - 21 May
Beautiful Woodstock Home with Fire Pit, Grill, and Mountain Charm
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 HK$1,446
HK$6,027 total
includes taxes & fees
4 Jun - 5 Jun
Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!
Living area

Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals
3.0 star property
Killington
The price is HK$1,494
HK$5,941 total
includes taxes & fees
19 May - 20 May
Breakaway House by Killington Vacation Rentals
Terrace/patio

Secluded Mountain Getaway with Hot tub and Views!

Secluded Mountain Getaway with Hot tub and Views!
Granville
10.0 out of 10, Exceptional, (3 reviews)
"Very nice place & convenient to Sugarbush & Rochester.We had 10 guys mountain biking in the area and worked out perfectly."
United States
Clint F.
The price is HK$951
HK$5,239 total
includes taxes & fees
20 May - 21 May
Secluded Mountain Getaway with Hot tub and Views!
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 HK$2,086
HK$4,626 total
includes taxes & fees
19 May - 20 May
large ski ranch hot tub close to killington pets ok
Interior

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 HK$1,494
HK$3,419 total
includes taxes & fees
19 May - 20 May
Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown
Interior

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, (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 HK$2,271
HK$4,318 total
includes taxes & fees
19 May - 20 May
180-degree panoramic views of Vermont's mountains from the living room and Deck
Outdoor spa tub

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 HK$1,558
HK$3,722 total
includes taxes & fees
23 May - 24 May
Walk to Pickle Barrel & Jax. Hot tub & Views
Smart TV, books

Cozy Moonship Yurt in the woods

Cozy Moonship Yurt in the woods
West Rutland
The price is HK$1,566
HK$2,938 total
includes taxes & fees
20 May - 21 May
Cozy Moonship Yurt in the woods
Exterior

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 HK$2,756
HK$6,946 total
includes taxes & fees
19 May - 20 May
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

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

10/10 Excellent
"Very clean hotel and helpful staff Didn’t love the ice maker in the freezer in the room would have preferred a hallway ice maker."
Barbara 2-night trip
Posted 1 hour ago
My Place Hotel-Randolph VT

Find out more about Stockbridge

Stockbridge Vacation Homes information

Number of reviews
163
Accommodation
723 Vacation Homes
Lowest Price
HK$1,123
Highest Price
HK$6,946

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