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

Holiday Homes in Stockbridge

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Stockbridge holiday homes

A living room with a wooden console table, a potted plant, and two clocks. A staircase and a fireplace with a TV are in the background.

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$868
includes taxes & fees
30 Sept - 1 Oct
Ski Home/Arcade Mountain Views Near Killington/Woodstock

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$789
includes taxes & fees
28 Sept - 29 Sept
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
A wooden cabin with a snow-covered ground, a wooden fence, and a door with a window above it.

3. Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
Killington
The price is AU$402
includes taxes & fees
28 Sept - 29 Sept
Luxury Condo Tucked in the Heart of Killington
A kitchen with a central island, two bar stools, pendant lights, and a view of the living area through an open archway.

4. 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.
Cozy Killington A-Frame w/ Hot Tub, Modern Kitchen & Forest Views – Near Skiing & Hiking Trails
A compact kitchen with a refrigerator, stove, microwave, and sink.

5. The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6

The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
Plymouth
The price is AU$817
includes taxes & fees
28 Sept - 29 Sept
The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
A bedroom with a bed, a nightstand, a window with a view of trees, and a framed picture on the wall.

6. Slopeside Estate Guesthouse: Hot tub, AC, Grill

Slopeside Estate Guesthouse: Hot tub, AC, Grill
Killington
The price is AU$1,354
includes taxes & fees
28 Sept - 29 Sept
Slopeside Estate Guesthouse: Hot tub, AC, Grill
A two-story house with a garage, solar panels, and a deck with outdoor furniture.

7. Secluded 5K Sq Ft Retreat: Sauna, Hot Tub & Games

Secluded 5K Sq Ft Retreat: Sauna, Hot Tub & Games
North Sherburne
9.4 out of 10, Exceptional, (24 reviews)
"House was beautiful & a great getaway for our group! "
United States
GiGi M.
Secluded 5K Sq Ft Retreat: Sauna, Hot Tub & Games
A wooden interior with a bench and shelves, a door with a handle, and a tiled floor.

8. The Outpost Double | Modern 2BR Ground Level Duplex | Exclusive Ski Deals

The Outpost Double | Modern 2BR Ground Level Duplex | Exclusive Ski Deals
Killington
10.0 out of 10, Exceptional, (1 review)
"Great amenitiesCleanNewAnd easy access to Starship Gondola at KillingtonWent with my two sons - we had a great time"
United States
Gifford F.
The price is AU$701
includes taxes & fees
28 Sept - 29 Sept
The Outpost Double | Modern 2BR Ground Level Duplex | Exclusive Ski Deals
A hallway with a wooden beam ceiling, a door with a frosted glass panel, and a view of a living room with a sofa and a table.

9. Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace

Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
Killington
The price is AU$697
includes taxes & fees
28 Sept - 29 Sept
Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace
A modern kitchen with a black stove, a red microwave, and a stainless steel sink. There are two black chairs and a black table.

10. 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$340
includes taxes & fees
28 Sept - 29 Sept
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
A spacious living area with a red sectional sofa, a wooden dining table, and a kitchen in the background.

11. Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
North Sherburne
10.0 out of 10, Exceptional, (1 review)
"Peak Hill, is a lovely and very clean home, with a fully stocked kitchen and comfy beds. This home is exactly as the pictures that are shown. We had a very small issue with the door lock (battery), called and it was fixed right away, wonderful service. The owner, Geri, we had the opportunity to meet and she is very kind and a pleasure to speak with. We travel alot and l bring pretty much my own kitchen, pillow...... with me where ever l go. However, l would of been fine using all at this...
United States
Essa R.
The price is AU$1,073
includes taxes & fees
30 Sept - 1 Oct
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
A living room with a wooden table, two chairs, a leather sofa, a coffee table, and a brick wall.

12. Liquid Lodge Lower: 2BR Duplex near Killington with 4 PM Checkout

Liquid Lodge Lower: 2BR Duplex near Killington with 4 PM Checkout
Killington
The price is AU$661
includes taxes & fees
28 Sept - 29 Sept
Liquid Lodge Lower: 2BR Duplex near Killington with 4 PM Checkout
A spacious living room with a fireplace, a television, and a large window.

13. 4BR Killington Home Perfect for Families, Pet-Friendly

4BR Killington Home Perfect for Families, Pet-Friendly
North Sherburne
10.0 out of 10, Exceptional, (23 reviews)
"Our group had a wonderful ski weekend at the house! It was well stocked with everything we needed and the fireplace was perfect to relax near after a day on the slopes. "
United States
Christina V.
The price is AU$1,042
includes taxes & fees
30 Sept - 1 Oct
4BR Killington Home Perfect for Families, Pet-Friendly
A forested area with a wooden structure and a red and blue playset.

14. 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, (72 reviews)
"Great stay. Killer location!"
United States
Matthew P.
The price is AU$1,220
includes taxes & fees
28 Sept - 29 Sept
25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.
A cozy living room with a sectional sofa, a coffee table, and a fireplace.

15. 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.
The price is AU$831
includes taxes & fees
28 Sept - 29 Sept
Breakaway House: Killington Duplex, Unit A. Hot Tub Close to Resort.
A cozy living room with a stone fireplace, a large sectional sofa, and a wooden ceiling.

16. The Tower House | Hot Tub | Firepit | Dog-Friendly

The Tower House | Hot Tub | Firepit | Dog-Friendly
Killington
6.8 out of 10, (3 reviews)
"Great place, near everything and great customer service!!"
United States
Patrick B.
The price is AU$1,065
includes taxes & fees
28 Sept - 29 Sept
The Tower House | Hot Tub | Firepit | Dog-Friendly
A modern living room with a red sectional sofa, a round coffee table, wooden ceiling beams, a kitchen area, and a balcony with a view of trees.

17. 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
10.0 out of 10, Exceptional, (1 review)
The price is AU$1,154
includes taxes & fees
30 Sept - 1 Oct
NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
A modern living room with a flat-screen TV, grey sofas, a dining table with chairs, and a large window with a view of greenery.

18. CozyDen - AC, Bike to Mountain, Porch!

CozyDen - AC, Bike to Mountain, Porch!
Killington
9.4 out of 10, Exceptional, (3 reviews)
"Place was clean and location was great"
United States
Berni H.
The price is AU$397
includes taxes & fees
1 Oct - 2 Oct
CozyDen - AC, Bike to Mountain, Porch!
A dining area with a wooden table, four chairs, a coffee maker, and a trash can.

19. 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
9.4 out of 10, Exceptional, (6 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.
The price is AU$779
includes taxes & fees
28 Sept - 29 Sept
Chittenden Farmhouse: Historic 4BR/2BA, 20 Min to Killington, 7 Min to Mountaintop Resort
A covered porch with a view of a white house and a green lawn.

20. 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
10.0 out of 10, Exceptional, (3 reviews)
"Lovely home with a beautiful property and accurate listing."
United States
Anonymous traveller
The price is AU$1,966
includes taxes & fees
28 Sept - 29 Sept
150 acres of serenity in Barnard VT new to vrbo, check our reviews elsewhere!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Stockbridge Hotel Reviews

The Jackson

The Jackson

10/10 Excellent
"Garden and grounds out back were very nice. Restaurant provided great dinner and breakfast."
Rick 2-night trip
Posted less than an hour ago
The Jackson

Find out more about Stockbridge

Stockbridge Holiday Homes information

Number of reviews
120
Accommodation
714 Holiday Homes
Lowest Price
AU$340
Highest Price
AU$1,966