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
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 NZ$955
includes taxes & fees
22 Sept - 23 Sept
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 NZ$955
includes taxes & fees
22 Sept - 23 Sept
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
A kitchen with white cabinetry, a stainless steel refrigerator, a coffee maker, and a dining area with two chairs.

3. Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
Killington
The price is NZ$498
includes taxes & fees
28 Sept - 29 Sept
Luxury Condo Tucked in the Heart of Killington
A spacious living area with a red sectional sofa, a wooden dining table, and a kitchen in the background.

4. 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 NZ$1,123
includes taxes & fees
22 Sept - 23 Sept
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
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.

5. 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)
NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
A spacious living room with a fireplace, large windows, and a television.

6. 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 NZ$1,276
includes taxes & fees
22 Sept - 23 Sept
4BR Killington Home Perfect for Families, Pet-Friendly
A cozy living room with a fireplace, a television, and a view of a snowy deck.

7. Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.

Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.
Killington
9.8 out of 10, Exceptional, (59 reviews)
"Perfect for a large group or a couple of families."
United States
Mark B.
The price is NZ$1,255
includes taxes & fees
23 Sept - 24 Sept
Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.
A two-story house with a garage, solar panels, and a deck with outdoor furniture.

8. 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 spacious living area with a fireplace, a television, and a dining area with natural light.

9. 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.
The price is NZ$979
includes taxes & fees
22 Sept - 23 Sept
Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.
A two-story house with a covered porch, a hot tub, and a stack of firewood.

10. 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, (71 reviews)
"Great stay. Killer location!"
United States
Matthew P.
The price is NZ$1,315
includes taxes & fees
23 Sept - 24 Sept
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.

11. 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 NZ$1,280
includes taxes & fees
22 Sept - 23 Sept
The Tower House | Hot Tub | Firepit | Dog-Friendly
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.

12. 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 NZ$472
includes taxes & fees
24 Sept - 25 Sept
CozyDen - AC, Bike to Mountain, Porch!
A cabin with a wooden deck, surrounded by lush greenery and a garden with purple flowers.

13. Fun In Fun Out Lower: 3BR with Den, Sauna and Sheltered Hot Tub

Fun In Fun Out Lower: 3BR with Den, Sauna and Sheltered 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.
The price is NZ$1,118
includes taxes & fees
22 Sept - 23 Sept
Fun In Fun Out Lower: 3BR with Den, Sauna and Sheltered 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.

14. 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 NZ$406
includes taxes & fees
23 Sept - 24 Sept
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
A covered porch with a view of a white house and a green lawn.

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
10.0 out of 10, Exceptional, (3 reviews)
"Lovely home with a beautiful property and accurate listing."
United States
Anonymous traveller
The price is NZ$2,351
includes taxes & fees
22 Sept - 23 Sept
150 acres of serenity in Barnard VT new to vrbo, check our reviews elsewhere!
A modern living room with a dark gray sectional sofa, a white armchair, a wooden coffee table, and a spiral staircase.

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

Slopeside Estate Guesthouse: Hot tub, AC, Grill
Killington
Slopeside Estate Guesthouse: Hot tub, AC, Grill
A bedroom with a bed, curtains, a radiator, and a view of the outside.

17. Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (16 reviews)
"The location was perfect, the property is very well maintained and comfortable. I would highly recommend this place!"
United States
Valerie
The price is NZ$333
includes taxes & fees
29 Sept - 30 Sept
Cozy Rutland Retreat
A spacious kitchen with a central island, wooden ceiling, and large windows.

18. Hot Tub Getaway - Near Killington - Sleeps 12

Hot Tub Getaway - Near Killington - Sleeps 12
Killington
The price is NZ$1,549
includes taxes & fees
22 Sept - 23 Sept
Hot Tub Getaway - Near Killington - Sleeps 12
A stone fireplace with a black mantel, framed picture, and decorative items.

19. 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 NZ$1,470
includes taxes & fees
22 Sept - 23 Sept
Snowarts- Game room, Fireplace, Close to golf!
A cozy living room with a sofa, armchair, and a bookshelf. There is a fireplace and a window providing natural light.

20. 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 NZ$1,237
includes taxes & fees
22 Sept - 23 Sept
Authentic farmhouse for those who love cozy, quirky, historical imperfection
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

Brandon Inn

Brandon Inn

8/10 Good
"I would stay again Old beautiful building I stayed on top floor and mostly used the stairs as only staff can operate the elevator"
Margaret 1-night trip
Posted 2 hours ago
Brandon Inn

Find out more about Stockbridge

Stockbridge Holiday Homes information

Number of reviews
12,120
Accommodation
704 Holiday Homes
Lowest Price
NZ$219
Highest Price
NZ$652