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
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Stockbridge holiday homes

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 €514
includes taxes & fees
8 Sept - 9 Sept
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
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.

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 €514
includes taxes & fees
8 Sept - 9 Sept
Ski Home/Arcade Mountain Views Near Killington/Woodstock
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.

3. 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 €537
includes taxes & fees
7 Sept - 8 Sept
NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
A kitchen with white cabinetry, a stainless steel refrigerator, a coffee maker, and a dining area with two chairs.

4. Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
Killington
The price is €235
includes taxes & fees
8 Sept - 9 Sept
Luxury Condo Tucked in the Heart of Killington
A two-story house with a covered porch, a hot tub, and a stack of firewood.

5. 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, (70 reviews)
"Great stay. Killer location!"
United States
Matthew P.
25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.
A cozy living room with a stone fireplace, a large sectional sofa, and a wooden ceiling.

6. 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 €584
includes taxes & fees
7 Sept - 8 Sept
The Tower House | Hot Tub | Firepit | Dog-Friendly
A bedroom with a wooden bed, a nightstand, a lamp, a window with blinds, and a wall-mounted light fixture.

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

Liquid Lodge Lower: 2BR Duplex near Killington with 4 PM Checkout
Killington
Liquid Lodge Lower: 2BR Duplex near Killington with 4 PM Checkout
A cozy living room with a sectional sofa, a coffee table, and a fireplace.

8. Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals
3.0 star property
Killington
Breakaway House by Killington Vacation Rentals
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.

9. 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 €234
includes taxes & fees
8 Sept - 9 Sept
CozyDen - AC, Bike to Mountain, Porch!
A wooden interior with a bench and shelves, a door with a handle, and a tiled floor.

10. 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 €426
includes taxes & fees
7 Sept - 8 Sept
The Outpost Double | Modern 2BR Ground Level Duplex | Exclusive Ski Deals
A cozy living room with a brick fireplace, a sofa, a coffee table, and a television mounted on a wooden cabinet.

11. 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, (21 reviews)
"Great location and excellent hosts "
United States
Peter G.
The price is €568
includes taxes & fees
8 Sept - 9 Sept
The Big Lebearski- AC, Grill, Fire Pit, Hot tub!
A modern kitchen with a black stove, a red microwave, and a stainless steel sink. There are two black chairs and a black table.

12. 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 €205
includes taxes & fees
7 Sept - 8 Sept
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
A cabin with a wooden deck, surrounded by lush greenery and a garden with purple flowers.

13. Fun In Fun Out Upper: 3BR with Two Decks, Sauna and Hot Tub

Fun In Fun Out Upper: 3BR with Two Decks, Sauna and Hot Tub
Killington
10.0 out of 10, Exceptional, (2 reviews)
"This was a perfect property for our quick vacation. The house is very well equipped and you have everything you need for a relaxing fun stay in Killington. The hot tub was great, and the house is in a very convenient location while fairly private at the same time. We really enjoyed our stay and would definitely recommend staying here."
United States
Linda D.
The price is €572
includes taxes & fees
7 Sept - 8 Sept
Fun In Fun Out Upper: 3BR with Two Decks, Sauna and Hot Tub
A stone fireplace with a black mantel, framed picture, and decorative items.

14. 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 €732
includes taxes & fees
9 Sept - 10 Sept
Snowarts- Game room, Fireplace, Close to golf!
A large house with a fire pit and outdoor seating.

15. 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, (2 reviews)
"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 €399
includes taxes & fees
5 Sept - 6 Sept
Beautiful 3-bedroom house with AC in charming Bridgewater
A covered porch with a view of a white house and a green lawn.

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
10.0 out of 10, Exceptional, (1 review)
"Light Hill is a beautiful property and the hosts are wonderful. We had a fantastic time there and our kids spent hours catching newts and frogs in the pond, swinging, and running around the yard. We enjoyed sitting on the screened in porch overlooking the mountains and just feeling very relaxed here. We are hoping to come back someday!"
United States
Andrew V.
150 acres of serenity in Barnard VT new to vrbo, check our reviews elsewhere!
A spacious living area with a fireplace, a television, and a dining area with natural light.

17. Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.

Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.
Killington
7.0 out of 10, Good, (6 reviews)
"Excellent brief stay."
United States
Ron L.
Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.
A cozy living room with a leather sofa, a wooden coffee table, and a large plant.

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 €453
includes taxes & fees
9 Sept - 10 Sept
HappyCub- AC, Hot Tub, Fire Pit, Game Room!
A cozy living room with a stone fireplace, a sofa set, and a dining table.

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.
The price is €564
includes taxes & fees
6 Sept - 7 Sept
Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna
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

The Jackson

The Jackson

10/10 Excellent
"We had a lovely 1 night stay at the quaint Jackson. We enjoyed the wine & cheese hour, had dinner at Oakes & Evelyn (on site but not part of the hotel) and enjoyed a nightcap on the porch. The bed was super comfortable, sheets were clean and crisp, robes were Frette and products smelled great. The property is gorgeous and Woodstock as a town is a delight."
Karl 1-night trip
Posted less than an hour ago
The Jackson

Find out more about Stockbridge

Stockbridge Holiday Homes information

Number of reviews
150
Accommodation
704 Holiday Homes
Lowest Price
€205
Highest Price
€732