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

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sep - 27 Sep
In four months
23 Oct - 25 Oct

Our top choices for Stockbridge vacation 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 AED 521
AED 2,182 total
includes taxes & fees
7 Jul - 8 Jul
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 AED 521
AED 2,182 total
includes taxes & fees
7 Jul - 8 Jul
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 AED 397
AED 527 total
includes taxes & fees
14 Jul - 15 Jul
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you
Property grounds

Modern Woodland Escape w Wshr dryer and Large Yard

Modern Woodland Escape w Wshr dryer and Large Yard
Ripton
The price is AED 413
AED 1,260 total
includes taxes & fees
5 Jul - 6 Jul
Modern Woodland Escape w Wshr dryer and Large Yard
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 AED 327
AED 844 total
includes taxes & fees
9 Jul - 10 Jul
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 AED 579
AED 1,915 total
includes taxes & fees
8 Jul - 9 Jul
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 AED 964
AED 3,206 total
includes taxes & fees
22 Jul - 23 Jul
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 AED 778
AED 2,259 total
includes taxes & fees
14 Jul - 15 Jul
Feel the real VT! Lakes, hikes, a foodies delight!
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 AED 735
AED 1,411 total
includes taxes & fees
6 Jul - 7 Jul
Cozy Moonship Yurt in the woods
Interior

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

CozyDen - AC, Grill, Bike to Mountain, Porch!
Killington
9.4 out of 10, Exceptional, (3 reviews)
"Place was clean and location was great"
United States
Berni H.
The price is AED 471
AED 1,013 total
includes taxes & fees
9 Jul - 10 Jul
CozyDen - AC, Grill, Bike to Mountain, Porch!
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 AED 1,966
AED 6,261 total
includes taxes & fees
6 Jul - 7 Jul
Breakaway House by Killington Vacation Rentals
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 AED 837
AED 2,631 total
includes taxes & fees
15 Jul - 16 Jul
The Tower House | Hot Tub | Firepit | Dog-Friendly
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 AED 696
AED 2,322 total
includes taxes & fees
6 Jul - 7 Jul
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
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 AED 519
AED 1,581 total
includes taxes & fees
8 Jul - 9 Jul
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, (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 AED 661
AED 1,551 total
includes taxes & fees
5 Jul - 6 Jul
Spacious Central 4BR, Ski, Bike,Hike, Explore Downtown
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 AED 705
AED 1,843 total
includes taxes & fees
19 Jul - 20 Jul
Modern Farm House…minutes to Okemo; 2 King beds!
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.
Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
TV, fireplace, Netflix, foosball

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 AED 658
AED 2,654 total
includes taxes & fees
8 Jul - 9 Jul
Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.
TV, fireplace, video games, foosball

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

Lakewood Lodge: 4BR/2.5BA Killington Home | Private Hot Tub, Wood Fire, Kent Pond & EV Charging

Lakewood Lodge: 4BR/2.5BA Killington Home | Private Hot Tub, Wood Fire, Kent Pond & EV Charging
Killington
10.0 out of 10, Exceptional, (1 review)
"Excellent, secluded location, super close to Killington. The property was very clean and everything seemed to work just fine. Water pressure in the bathroom sinks was strangely low, but shower pressure was good. Hot tub was wonderful after skiing all day.The host is amazing! Very attentive and proactive in reaching out with info. I'd definitely rent this house again!"
United States
Brett H.
Lakewood Lodge: 4BR/2.5BA Killington Home | Private Hot Tub, Wood Fire, Kent Pond & EV Charging
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

Hampton Inn Rutland

Hampton Inn Rutland

10/10 Excellent
"My room was perfect. The staff was helpful. Plenty of parking. Breakfast was delicious."
Bernadette 2-night trip
Posted 1 hour ago
Hampton Inn Rutland

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