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
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 holiday homes

Interior

1. 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 £424
includes taxes & fees
16 Aug - 17 Aug
Ski Home/Arcade Mountain Views Near Killington/Woodstock
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 £424
includes taxes & fees
16 Aug - 17 Aug
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Coffee/tea maker, fridge, microwave, oven

3. Cozy Killington A-Frame w/ Hot Tub, Modern Kitchen & Forest Views – Near Skiing & Hiking Trails

Cozy Killington A-Frame w/ Hot Tub, Modern Kitchen & Forest Views – Near Skiing & Hiking Trails
North Sherburne
10.0 out of 10, Exceptional, (1 review)
"Great property to stay at highly recommend and will hopefully be staying again soon!"
United States
Robert R.
The price is £553
includes taxes & fees
18 Aug - 19 Aug
Cozy Killington A-Frame w/ Hot Tub, Modern Kitchen & Forest Views – Near Skiing & Hiking Trails
TV, offices

4. 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 £489
includes taxes & fees
25 Aug - 26 Aug
The Tower House | Hot Tub | Firepit | Dog-Friendly
House, 6 Bedrooms | Living area

5. Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals
3.0 star property
Killington
The price is £553
includes taxes & fees
16 Aug - 17 Aug
Breakaway House by Killington Vacation Rentals
Private kitchen

6. 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 £175
includes taxes & fees
24 Aug - 25 Aug
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
TV, fireplace, video games, table football

7. 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 £553
includes taxes & fees
18 Aug - 19 Aug
25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.
Interior

8. 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.
CozyDen - AC, Grill, Bike to Mountain, Porch!
Interior

9. Private Killington Home w/ Indoor Hot Tub and 2 Living Rooms

Private Killington Home w/ Indoor Hot Tub and 2 Living Rooms
North Sherburne
The price is £565
includes taxes & fees
18 Aug - 19 Aug
Private Killington Home w/ Indoor Hot Tub and 2 Living Rooms
Property grounds

10. Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.

Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.
Killington
10.0 out of 10, Exceptional, (1 review)
"Such an awesome place! The booking/check-in process was seamless and the location cannot be beat! Will definitely be booking again. "
United States
Catherine S.
Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.
TV, streaming services, music library, video library

11. Breakaway House: Killington Duplex, Unit A. Hot Tub Close to Resort.

Breakaway House: Killington Duplex, Unit A. Hot Tub Close to Resort.
Killington
7.6 out of 10, Good, (4 reviews)
"Great location, clean and quiet."
United States
Dr. Stephan B.
Breakaway House: Killington Duplex, Unit A. Hot Tub Close to Resort.
Smart TV, fireplace

12. 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.
The price is £490
includes taxes & fees
24 Aug - 25 Aug
Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna
Smart TV, fireplace, video games, stereo

13. 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 £488
includes taxes & fees
20 Aug - 21 Aug
The Big Lebearski- AC, Grill, Fire Pit, Hot tub!
Smart TV, fireplace

14. Renovated 4BR House w/ Hot Tub & Fire Pit: Near Killington Lifts & Dining

Renovated 4BR House w/ Hot Tub & Fire Pit: Near Killington Lifts & Dining
Killington
10.0 out of 10, Exceptional, (3 reviews)
"great rental overall, the unit was well stocked, clean and have everything you need for your stay."
United States
matt d.
The price is £821
includes taxes & fees
16 Aug - 17 Aug
Renovated 4BR House w/ Hot Tub & Fire Pit: Near Killington Lifts & Dining
Terrace/patio

15. 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 £950
includes taxes & fees
20 Aug - 21 Aug
150 acres of serenity in Barnard VT new to vrbo, check our reviews elsewhere!
Interior

16. Snowarts- Game room, Fireplace, Close to golf!

Snowarts- Game room, Fireplace, Close to golf!
Killington
9.0 out of 10, Wonderful, (2 reviews)
"Great place for a large group. It was pet friendly and that is a plus for us. Very clean and reasonably priced."
United States
Tammy W.
The price is £658
includes taxes & fees
16 Aug - 17 Aug
Snowarts- Game room, Fireplace, Close to golf!
TV, fireplace

17. 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.
The price is £521
includes taxes & fees
17 Aug - 18 Aug
Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
Smart TV, fireplace, video games, stereo

18. HappyCub- AC, Hot Tub, Fire Pit, Game Room!

HappyCub- AC, Hot Tub, Fire Pit, Game Room!
Killington
10.0 out of 10, Exceptional, (27 reviews)
"Great communication, location, and all around stay!"
United States
Ashley K.
The price is £390
includes taxes & fees
20 Aug - 21 Aug
HappyCub- AC, Hot Tub, Fire Pit, Game Room!
Smart TV, fireplace, video games, books

19. Authentic farmhouse for those who love cozy, quirky, historical imperfection

Authentic farmhouse for those who love cozy, quirky, historical imperfection
Randolph Center
10.0 out of 10, Exceptional, (6 reviews)
"The rental experience was seemless....communication was great, the property fit our family so easily and the location was easily accessible to many beautiful spots. The home is well equipped and it was a delightful stay!"
United States
Kathy K.
The price is £420
includes taxes & fees
2 Sept - 3 Sept
Authentic farmhouse for those who love cozy, quirky, historical imperfection
Smart TV, fireplace

20. Alpine Chalet Grill, Fire pit, Pool, Gym, CornHole

Alpine Chalet Grill, Fire pit, Pool, Gym, CornHole
Killington
10.0 out of 10, Exceptional, (6 reviews)
"Such a great spot."
United States
Kathleen G.
The price is £698
includes taxes & fees
19 Aug - 20 Aug
Alpine Chalet Grill, Fire pit, Pool, Gym, CornHole
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

Holiday Inn Express Hotel & Suites White River Junction by IHG

Holiday Inn Express Hotel & Suites White River Junction by IHG

10/10 Excellent
"Clean, spacious rooms."
Josh 1-night trip
Posted 8 hours ago
Holiday Inn Express Hotel & Suites White River Junction by IHG

Find out more about Stockbridge

Stockbridge Holiday Homes information

Number of reviews
153
Accommodation
698 Holiday Homes
Lowest Price
£202
Highest Price
£950