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

Stockbridge Vacation Rentals

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Stockbridge vacation rentals

Property grounds

1. Gnome Home Mountain Ski Chalet w/Sauna Killington

Gnome Home Mountain Ski Chalet w/Sauna Killington
Stockbridge
10.0 out of 10, Exceptional, (5 reviews)
"Nice property in a beautiful location. Host was very responsive and informative. Thanks for the stay!"
United States
Gerald S.
The price is ￥37,478
￥83,193 total
includes taxes & fees
Aug 31 - Sep 1
Gnome Home Mountain Ski Chalet w/Sauna Killington
Exterior

2. 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 ￥27,714
￥100,184 total
includes taxes & fees
Aug 9 - Aug 10
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Interior

3. 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 ￥27,714
￥100,184 total
includes taxes & fees
Aug 9 - Aug 10
Ski Home/Arcade Mountain Views Near Killington/Woodstock
Aerial view

4. Mountain Green

Mountain Green
2.0 star property
Killington
7.2 out of 10, Good, (29 reviews)
"The property is under major construction which was not disclosed when booking. The management fee was almost as much as the room rate, clearer description at time of booking would be appreciated."
United States
Keith
The price is ￥12,313
￥36,717 total
includes taxes & fees
Aug 12 - Aug 13
Mountain Green
1 bedroom, desk, iron/ironing board, travel crib

5. Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym

Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym
Killington
10.0 out of 10, Exceptional, (15 reviews)
"Host was very responsive and the home was great! "
United States
Rebecca B.
The price is ￥19,967
￥43,156 total
includes taxes & fees
Aug 11 - Aug 12
Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym
Coffee/tea maker, fridge, microwave, oven

6. Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532

Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532
Killington
9.6 out of 10, Exceptional, (69 reviews)
"Cozy space close to the mountain. Host was very responsive and check in and check out was easy. "
United States
Spencer P.
Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532
Aerial view

7. The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
The Suites at Killington Center
Outdoor dining

8. Fabulous 4-bedroom chalet in tranquil Killington getaway with gorgeous Hot tub

Fabulous 4-bedroom chalet in tranquil Killington getaway with gorgeous Hot tub
North Sherburne
8.2 out of 10, Very Good, (13 reviews)
"We had a great time!"
United States
Matthew R.
The price is ￥23,427
￥70,686 total
includes taxes & fees
Aug 25 - Aug 26
Fabulous 4-bedroom chalet in tranquil Killington getaway with gorgeous Hot tub
TV, fireplace, DVD player, books

9. Resort condo with mountain views, full kitchen, and free WiFi

Resort condo with mountain views, full kitchen, and free WiFi
Killington
8.8 out of 10, Excellent, (47 reviews)
"Great location. Great amenities. Great communication. "
United States
Jason B.
The price is ￥10,601
￥53,886 total
includes taxes & fees
Aug 12 - Aug 13
Resort condo with mountain views, full kitchen, and free WiFi
House, 6 Bedrooms | Living area

10. Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals
3.0 star property
Killington
Breakaway House by Killington Vacation Rentals
Living area

11. Killington condo 5 min to killington resort

Killington condo 5 min to killington resort
Killington
9.4 out of 10, Exceptional, (9 reviews)
"Great location!!"
United States
Nicholas C.
The price is ￥17,828
￥53,813 total
includes taxes & fees
Aug 16 - Aug 17
Killington condo 5 min to killington resort
Dining

12. Gorgeous 2BR/2BA Woods Condo: Pool, Hot Tub, Spa/ Discounted Ski Rentals. V5

Gorgeous 2BR/2BA Woods Condo: Pool, Hot Tub, Spa/ Discounted Ski Rentals. V5
The Woods
10.0 out of 10, Exceptional, (14 reviews)
"Great place to stay. Responsive host, very clean place. Close to amenities. Would definitely recommend and stay again!"
United States
Darlene D.
Gorgeous 2BR/2BA Woods Condo: Pool, Hot Tub, Spa/ Discounted Ski Rentals. V5
TV, fireplace, Netflix, streaming services

13. Killington Cabin: Right Unit - Sleeps 10 in 4 BR, 2 BA Cozy Escape

Killington Cabin: Right Unit - Sleeps 10 in 4 BR, 2 BA Cozy Escape
Killington
9.8 out of 10, Exceptional, (65 reviews)
"Amazing location, cozy cabin with plenty of beds for sleeping , owners were super responsive will def love to stay again!"
United States
Robert D.
Killington Cabin: Right Unit - Sleeps 10 in 4 BR, 2 BA Cozy Escape
Indoor pool, a heated pool

14. Trail Creek Killington Condos #18: Ski Home Trail. Bus. Hot Tub. Pool.

Trail Creek Killington Condos #18: Ski Home Trail. Bus. Hot Tub. Pool.
Killington
10.0 out of 10, Exceptional, (12 reviews)
"Great Location"
United States
Brian B.
Trail Creek Killington Condos #18: Ski Home Trail. Bus. Hot Tub. Pool.
Interior

15. Killington Cabin - Left Unit: Great for families, Cozy, Close to Mountain. Hot Tub. Wood Stove.

Killington Cabin - Left Unit: Great for families, Cozy, Close to Mountain. Hot Tub. Wood Stove.
Killington
9.6 out of 10, Exceptional, (21 reviews)
"Cozy, classic, basic, old school Killington condo. Loved the wood stove. Easy access to Killington area. "
United States
Leslie P.
Killington Cabin - Left Unit: Great for families, Cozy, Close to Mountain. Hot Tub. Wood Stove.
TV, fireplace, video games, foosball

16. 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.
The price is ￥27,230
￥118,542 total
includes taxes & fees
Aug 12 - Aug 13
25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.
Property grounds

17. Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around

Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around
Hancock
10.0 out of 10, Exceptional, (5 reviews)
"The host was easy to communicate with, gracious and helpful. Amenities were generous and everything was in excellent condition. Really enjoyed the quiet treed setting and the hot tub."
United States
Elizabeth N.
The price is ￥28,525
￥76,497 total
includes taxes & fees
Aug 9 - Aug 10
Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around
Coffee/tea maker, fridge, microwave, oven

18. Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Leicester
10.0 out of 10, Exceptional, (87 reviews)
"Definitely super SUPER clean all throughout! The ambiance is perfect, just a beautiful cottage with all the amenities you might need. Perfect place to stay."
United States
Julian V.
The price is ￥18,818
￥30,128 total
includes taxes & fees
Aug 16 - Aug 17
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Interior

19. Trailside Village #7: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals

Trailside Village #7: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
Killington
9.4 out of 10, Exceptional, (63 reviews)
"Good place. Hosts were in touch and the hot tub was great. "
United States
Bethany S.
The price is ￥29,208
￥85,558 total
includes taxes & fees
Aug 11 - Aug 12
Trailside Village #7: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
Smart TV, fireplace, video games, stereo

20. 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 ￥54,640
￥123,703 total
includes taxes & fees
Aug 9 - Aug 10
The Big Lebearski- AC, Grill, Fire Pit, Hot tub!
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

Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Amazing! Will visit again."
Leah 4-night trip
Posted 4 hours ago
Woodstock Inn & Resort

Find out more about Stockbridge

Search for holiday rentals in Stockbridge on Expedia! You can easily find your home rentals, villas, holiday apartments in Stockbridge using one of the methods below:

  • View our selection of featured holiday rentals in Stockbridge
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  • Enter your travel dates to view the best deals on holiday rentals in Stockbridge while they last

Look no further and take a look at our great range of rental properties in Stockbridge!

Frequently asked questions

Are there vacation rentals in Stockbridge?

Yes, we give you a choice of vacation rentals near the most popular sights in Stockbridge, or you can select a more remote option if you want a relaxing place to stay.

What's the top vacation rental that Stockbridge has to offer?

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly: Visitors like this Stockbridge vacation home rental. It is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books.

How many vacation rentals are there in Stockbridge?

With 11 Expedia vacation rentals, you're sure to find just the right place for your Stockbridge stay.

What’s there to see and do in Stockbridge?

While exploring the area, visit family-friendly sights like Sugarbush Farm, or get outside and enjoy nature at Green Mountain National Forest. Les Newell Wildlife Management Area and Belcher Library are other places to visit while you're in town.

What’s a vacation rental in Stockbridge like?

A vacation rental is a private property where you can stay for several days or longer in Stockbridge. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from public hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for a family getaway.