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

Stockbridge Holiday Rentals

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Stockbridge holiday rentals

Exterior

1. 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$1,044
HK$4,607 total
includes taxes & fees
19 Aug - 20 Aug
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Property grounds

2. 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 HK$1,778
HK$4,042 total
includes taxes & fees
30 Aug - 31 Aug
Gnome Home Mountain Ski Chalet w/Sauna Killington
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 HK$1,114
HK$4,694 total
includes taxes & fees
23 Aug - 24 Aug
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 HK$612
HK$1,826 total
includes taxes & fees
19 Aug - 20 Aug
Mountain Green
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 HK$1,108
HK$3,460 total
includes taxes & fees
19 Aug - 20 Aug
Fabulous 4-bedroom chalet in tranquil Killington getaway with gorgeous Hot tub
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, (71 reviews)
"Cozy space close to the mountain. Host was very responsive and check in and check out was easy. "
United States
Spencer P.
The price is HK$837
HK$2,791 total
includes taxes & fees
19 Aug - 20 Aug
Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532
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 HK$883
HK$2,664 total
includes taxes & fees
23 Aug - 24 Aug
Killington condo 5 min to killington resort
Smart TV, fireplace

8. Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything

Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
Killington
10.0 out of 10, Exceptional, (21 reviews)
"Cannon was cozy, clean, and as described. "
United States
Addams S.
The price is HK$1,116
HK$3,613 total
includes taxes & fees
19 Aug - 20 Aug
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
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 HK$527
HK$2,679 total
includes taxes & fees
25 Aug - 26 Aug
Resort condo with mountain views, full kitchen, and free WiFi
1 bedroom, desk, iron/ironing board, travel cot

10. 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, (16 reviews)
"Great condo and building. Everything in excellent condition. Convenient location."
United States
Joseph S.
The price is HK$988
HK$2,136 total
includes taxes & fees
19 Aug - 20 Aug
Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym
Smart TV, offices

11. NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking

NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
North Sherburne
The price is HK$1,469
HK$4,939 total
includes taxes & fees
19 Aug - 20 Aug
NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
Aerial view

12. The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
The price is HK$1,183
HK$3,027 total
includes taxes & fees
20 Aug - 21 Aug
The Suites at Killington Center
Coffee/tea maker, fridge, microwave, oven

13. 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 HK$932
HK$1,500 total
includes taxes & fees
19 Aug - 20 Aug
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Smart TV

14. Relaxing Mountain Condo Steps from Killington Resort; Views, Pool & Shuttle!

Relaxing Mountain Condo Steps from Killington Resort; Views, Pool & Shuttle!
Killington
9.8 out of 10, Exceptional, (188 reviews)
"The condo was in excellent condition and very clean. Great location too. Owner was very responsive. "
United States
Michael V.
The price is HK$1,059
HK$1,374 total
includes taxes & fees
19 Aug - 20 Aug
Relaxing Mountain Condo Steps from Killington Resort; Views, Pool & Shuttle!
Private kitchen

15. 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$727
HK$1,850 total
includes taxes & fees
25 Aug - 26 Aug
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
TV, fireplace, Netflix, streaming services

16. 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.
The price is HK$1,041
HK$3,995 total
includes taxes & fees
19 Aug - 20 Aug
Killington Cabin: Right Unit - Sleeps 10 in 4 BR, 2 BA Cozy Escape
Smart TV, fireplace, video games, books

17. 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 HK$1,285
HK$3,235 total
includes taxes & fees
19 Aug - 20 Aug
FirBear- AC, Pool, Hot Tub, Sauna, Tennis, Gym
Property grounds

18. CubsCorner - Pool, Sauna, Gym, Close to Mountain!

CubsCorner - Pool, Sauna, Gym, Close to Mountain!
Killington
10.0 out of 10, Exceptional, (6 reviews)
"Great location with access to both Pico and Killington Mountains!"
United States
Olaf G.
The price is HK$1,805
HK$3,606 total
includes taxes & fees
20 Aug - 21 Aug
CubsCorner - Pool, Sauna, Gym, Close to Mountain!
Terrace/patio

19. CozyCub- Pool, AC, Hiking, Mountain Biking, Tennis

CozyCub- Pool, AC, Hiking, Mountain Biking, Tennis
Killington
9.8 out of 10, Exceptional, (26 reviews)
"Great trip!"
United States
casey d.
The price is HK$955
HK$2,151 total
includes taxes & fees
20 Aug - 21 Aug
CozyCub- Pool, AC, Hiking, Mountain Biking, Tennis
Interior

20. 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.
The price is HK$1,013
HK$3,954 total
includes taxes & fees
19 Aug - 20 Aug
Killington Cabin - Left Unit: Great for families, Cozy, Close to Mountain. Hot Tub. Wood Stove.
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

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

10/10 Excellent
"I had a pleasant two-night stay. The hotel was very quiet, the staff were very welcoming, and I really enjoyed the pool."
Mathieu 2-night trip
Posted 10 hours ago
Days Inn by Wyndham Rutland/Killington Area

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
  • Use the map to find apartments and other holiday homes in the Stockbridge neighbourhood you prefer
  • 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 holiday rentals in Stockbridge?

Yes, there are holiday rentals close to the most popular sights in Stockbridge, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Stockbridge has to offer?

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly: This holiday home rental outside of Stockbridge is located on a lake, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books.

How many holiday rentals are there in Stockbridge?

With 11 Expedia holiday rentals, you're guaranteed 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 Killington Adventure Center, 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 holiday rental in Stockbridge like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Stockbridge. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll have everything you want. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from public hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for a small group gathering.