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

Holiday Homes in Stockbridge

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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 AU$853
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 AU$850
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 AU$1,058
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 AU$924
includes taxes & fees
1 Sept - 2 Sept
The Tower House | Hot Tub | Firepit | Dog-Friendly
Dining

5. Chittenden Farmhouse: Historic 4BR/2BA, 20 Min to Killington, 7 Min to Mountaintop Resort

Chittenden Farmhouse: Historic 4BR/2BA, 20 Min to Killington, 7 Min to Mountaintop Resort
Chittenden
9.2 out of 10, Wonderful, (5 reviews)
"Loved this stay - the farmhouse is authentic and oozes charm! Everything about this stay was easy - 20min drive to the slopes, 15 min to downtown Rutland, and an extremely well-equipped house to easily accommodate the six of us. Superb communication from the host both prior to and during our stay (promptly answered several questions for us). If you want a vintage farmhouse feel as opposed to a modern condo-style stay, this is the place for you!"
United States
Carl P.
Chittenden Farmhouse: Historic 4BR/2BA, 20 Min to Killington, 7 Min to Mountaintop Resort
TV, streaming services, music library, video library

6. 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.
House, 6 Bedrooms | Living area

7. Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals
3.0 star property
Killington
Breakaway House by Killington Vacation Rentals
Smart TV

8. Family and friend friendly upper ski cabin with bunks, sleeps 8

Family and friend friendly upper ski cabin with bunks, sleeps 8
Killington
Family and friend friendly upper ski cabin with bunks, sleeps 8
Private kitchen

9. 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 AU$334
includes taxes & fees
17 Aug - 18 Aug
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Coffee/tea maker, fridge, microwave, oven

10. Summit House on George | Renovated | 5 Mins to K-1 | Lift & Rental Deals

Summit House on George | Renovated | 5 Mins to K-1 | Lift & Rental Deals
Killington
10.0 out of 10, Exceptional, (1 review)
"Absolutely loved this house. Our stay was perfect. It was so close to the mountain and all the restaurants. It was not on a busy street, so private and clean and overall amazing place to stay. We would definitely choose to stay again here!!"
United States
Sandra G.
Summit House on George | Renovated | 5 Mins to K-1 | Lift & Rental Deals
Exterior

11. Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley
Warren
10.0 out of 10, Exceptional, (26 reviews)
"We had a great time! "
United States
Allie T.
Beautiful home located in the Mad River Valley
Smart TV, fireplace, video games, stereo

12. 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 AU$908
includes taxes & fees
20 Aug - 21 Aug
The Big Lebearski- AC, Grill, Fire Pit, Hot tub!
Property grounds

13. 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.
Smart TV, fireplace, video games, stereo

14. 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 AU$776
includes taxes & fees
16 Aug - 17 Aug
HappyCub- AC, Hot Tub, Fire Pit, Game Room!
Interior

15. 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 AU$1,198
includes taxes & fees
19 Aug - 20 Aug
Snowarts- Game room, Fireplace, Close to golf!
Terrace/patio

16. 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 AU$1,805
includes taxes & fees
20 Aug - 21 Aug
150 acres of serenity in Barnard VT new to vrbo, check our reviews elsewhere!
Terrace/patio

17. Secluded Mountain Getaway with Hot tub and Views!

Secluded Mountain Getaway with Hot tub and Views!
Granville
8.8 out of 10, Excellent, (5 reviews)
"Very nice place & convenient to Sugarbush & Rochester.We had 10 guys mountain biking in the area and worked out perfectly."
United States
Clint F.
Secluded Mountain Getaway with Hot tub and Views!
Smart TV, fireplace

18. 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 AU$917
includes taxes & fees
24 Aug - 25 Aug
Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna
Property grounds

19. Beautiful 3-bedroom house with AC in charming Bridgewater

Beautiful 3-bedroom house with AC in charming Bridgewater
Bridgewater
10.0 out of 10, Exceptional, (1 review)
"Great house with fun decorations. Comfortable with lots of room; full kitchen with ample dining area. Loved the coffee available and the sound machine in the bedroom- great conveniences! Communication around booking were great with easy check in and check out."
United States
Susan S.
The price is AU$694
includes taxes & fees
13 Sept - 14 Sept
Beautiful 3-bedroom house with AC in charming Bridgewater
Dining

20. large ski ranch hot tub close to killington pets ok

large ski ranch hot tub close to killington pets ok
Mendon
9.2 out of 10, Wonderful, (5 reviews)
"The hot tub was great after a day of skiing."
United States
Callison A.
The price is AU$659
includes taxes & fees
16 Aug - 17 Aug
large ski ranch hot tub close to killington pets ok
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

Mountain Meadows Lodge

Mountain Meadows Lodge

10/10 Excellent
"Great place, we stopped for a few days while taking a break from hiking the AT. The grounds are amazing, breakfast was delicious, and staff was very accommodating. They even washing our stinky hiking clothes and picked up a pizza for us. Would highly recommend!"
Matthew 1-night trip
Posted 2 hours ago
Mountain Meadows Lodge

Find out more about Stockbridge

Stockbridge Holiday Homes information

Number of reviews
106
Accommodation
704 Holiday Homes
Lowest Price
AU$659
Highest Price
AU$1,805