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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

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 SAR 1,053
SAR 2,189 total
includes taxes & fees
7 Sep - 8 Sep
Gnome Home Mountain Ski Chalet w/Sauna Killington
Interior

2. 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 SAR 822
SAR 2,616 total
includes taxes & fees
27 Aug - 28 Aug
Ski Home/Arcade Mountain Views Near Killington/Woodstock
Exterior

3. 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 SAR 822
SAR 2,616 total
includes taxes & fees
27 Aug - 28 Aug
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Terrace/patio

4. 150 acres of serenity in Barnard VT new to vrbo, check our reviews elsewhere!

150 acres of serenity in Barnard VT new to vrbo, check our reviews elsewhere!
Bethel
The price is SAR 2,534
SAR 4,840 total
includes taxes & fees
27 Aug - 28 Aug
150 acres of serenity in Barnard VT new to vrbo, check our reviews elsewhere!
Outdoor dining

5. 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 SAR 558
SAR 1,691 total
includes taxes & fees
27 Aug - 28 Aug
Fabulous 4-bedroom chalet in tranquil Killington getaway with gorgeous Hot tub
House, 2 Bedrooms | Private kitchen | Coffee/tea maker, fridge, oven, toaster

6. Killington A-frame 2 Bedroom Home

Killington A-frame 2 Bedroom Home
3.0 star property
North Sherburne
The price is SAR 1,262
SAR 2,446 total
includes taxes & fees
18 Aug - 19 Aug
Killington A-frame 2 Bedroom Home
Living area

7. 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 SAR 422
SAR 1,275 total
includes taxes & fees
27 Aug - 28 Aug
Killington condo 5 min to killington resort
Property grounds

8. BearHaus Central AC, HUGE Hot Tub, Awesome FirePit

BearHaus Central AC, HUGE Hot Tub, Awesome FirePit
Killington
9.6 out of 10, Exceptional, (5 reviews)
"Great property - excellent hosts. Close to mountain and restaurants"
United States
Eric D.
BearHaus Central AC, HUGE Hot Tub, Awesome FirePit
Smart TV, fireplace, video games, stereo

9. 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 Big Lebearski- AC, Grill, Fire Pit, Hot tub!
Exterior

10. BearRight- AC, Pool, Hot Tub, Grill, FirePit

BearRight- AC, Pool, Hot Tub, Grill, FirePit
Killington
9.8 out of 10, Exceptional, (13 reviews)
"Place was perfect for us for a group ski weekend."
United States
Kevin F.
BearRight- AC, Pool, Hot Tub, Grill, FirePit
TV, fireplace, video games, foosball

11. 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.
Exterior

12. Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.

Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
Killington
9.2 out of 10, Wonderful, (7 reviews)
"Beautiful place . My sister was visiting USA/ Vermont for the first time . We went to the Breakfast cafe next door it was amazing . "
United States
Asad B.
The price is SAR 311
SAR 1,002 total
includes taxes & fees
18 Aug - 19 Aug
Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
1 bedroom, iron/ironing board, WiFi (free), bed sheets

13. Ski Condo Close to Killington: Discounted Ski Rentals and Shuttle Bus. Killington Center 631

Ski Condo Close to Killington: Discounted Ski Rentals and Shuttle Bus. Killington Center 631
Killington
8.8 out of 10, Excellent, (6 reviews)
"Easy, convenient location. Perfect no frills last minute ski trip. Would stay again. Good communication."
United States
Marcus G.
The price is SAR 271
SAR 944 total
includes taxes & fees
17 Aug - 18 Aug
Ski Condo Close to Killington: Discounted Ski Rentals and Shuttle Bus. Killington Center 631
Dining

14. The Swirl Suite at Killington: Renovated 2RM/2BA Suite. Sleeps 6. Discounted Ski Rentals.

The Swirl Suite at Killington: Renovated 2RM/2BA Suite. Sleeps 6. Discounted Ski Rentals.
Killington
9.2 out of 10, Wonderful, (9 reviews)
"Fantastic place to stay, beds were great. It was wonderful having two full baths. Would definitely recommend this gem again!"
United States
Dawn B.
The price is SAR 441
SAR 1,336 total
includes taxes & fees
17 Aug - 18 Aug
The Swirl Suite at Killington: Renovated 2RM/2BA Suite. Sleeps 6. Discounted Ski Rentals.
Smart TV, fireplace, video games, books

15. FirBear- AC, Pool, Hot Tub, Sauna, Tennis, Gym

FirBear- AC, Pool, Hot Tub, Sauna, Tennis, Gym
The Woods
10.0 out of 10, Exceptional, (24 reviews)
"Loved the pool, sauna, and steam room. Really nice place, everything we needed. "
United States
Lisa N.
The price is SAR 773
SAR 1,752 total
includes taxes & fees
19 Aug - 20 Aug
FirBear- AC, Pool, Hot Tub, Sauna, Tennis, Gym
Dining

16. Snowcub- AC, Pool, Hot tub, Tennis, Grill!

Snowcub- AC, Pool, Hot tub, Tennis, Grill!
The Woods
10.0 out of 10, Exceptional, (26 reviews)
"We loved our stay at Snowcub! The condo is beautiful, welcoming and our hosts had excellent communication. We were comfortable and enjoyed the nice amenities- including a pool and hot tub! We would love to stay here again! We loved it! "
United States
Maura A.
Snowcub- AC, Pool, Hot tub, Tennis, Grill!
Condo, 2 Bedrooms | Living area

17. The Woods by Killington Vacation Rentals - 2 Bedrooms

The Woods by Killington Vacation Rentals - 2 Bedrooms
3.0 star property
The Woods
10.0 out of 10, Exceptional, (3 reviews)
"The condo had everything we needed for a comfortable and enjoyable stay. The pool and hot tub area were great additions. We would definitely stay again."
United States
Paul
The price is SAR 872
SAR 2,461 total
includes taxes & fees
31 Aug - 1 Sep
The Woods by Killington Vacation Rentals - 2 Bedrooms
6 bedrooms, desk, iron/ironing board, travel crib

18. DoubleDen- AC, Hot Tub, Fire pit, Grill, Game Room

DoubleDen- AC, Hot Tub, Fire pit, Grill, Game Room
Killington
10.0 out of 10, Exceptional, (26 reviews)
"Ver accommodating the property was amazing. "
United States
Jessica M.
DoubleDen- AC, Hot Tub, Fire pit, Grill, Game Room
Smart TV, fireplace

19. Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna

Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna
The Woods
10.0 out of 10, Exceptional, (7 reviews)
"Great location and a great place. Felt right at home"
United States
Tyler B.
Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna
Terrace/patio

20. Estelle Cottage- Private Sauna, Hot tub, Pool, AC

Estelle Cottage- Private Sauna, Hot tub, Pool, AC
The Woods
10.0 out of 10, Exceptional, (1 review)
"Beautiful home and location. Great communication with host. I highly recommend this home, and will definitely book again."
United States
Edward M.
Estelle Cottage- Private Sauna, Hot tub, Pool, AC
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

Align Inn Vermont

Align Inn Vermont

10/10 Excellent
"Was a great place to stay within walking distance of Quechee Gorge. An ideal location and very clean."
Samantha 1-night trip
Posted 7 hours ago
Align Inn Vermont

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.

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.