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

Stockbridge Vacation Rentals

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Stockbridge vacation 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 CA $199
CA $837 total
includes taxes & fees
Sep 22 - Sep 23
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 CA $199
CA $837 total
includes taxes & fees
Sep 22 - Sep 23
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Coffee/tea maker, fridge, microwave, oven

3. Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
Killington
The price is CA $125
CA $402 total
includes taxes & fees
Sep 23 - Sep 24
Luxury Condo Tucked in the Heart of Killington
Coffee/tea maker, fridge, microwave, oven

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.
The price is CA $311
CA $1,065 total
includes taxes & fees
Sep 27 - Sep 28
Cozy Killington A-Frame w/ Hot Tub, Modern Kitchen & Forest Views – Near Skiing & Hiking Trails
Interior

5. 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 CA $176
CA $381 total
includes taxes & fees
Sep 24 - Sep 25
CozyDen - AC, Bike to Mountain, Porch!
TV

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

Slopeside Estate Guesthouse: Hot tub, AC, Grill
Killington
The price is CA $210
CA $1,386 total
includes taxes & fees
Sep 20 - Sep 21
Slopeside Estate Guesthouse: Hot tub, AC, Grill
Private kitchen

7. 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 CA $130
CA $328 total
includes taxes & fees
Sep 30 - Oct 1
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
1 bedroom, desk, WiFi (free), bed sheets

8. 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 CA $136
CA $266 total
includes taxes & fees
Sep 20 - Sep 21
Cozy Rutland Retreat
TV, offices

9. 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 CA $345
CA $1,037 total
includes taxes & fees
Sep 20 - Sep 21
The Tower House | Hot Tub | Firepit | Dog-Friendly
Interior

10. 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 CA $601
CA $1,213 total
includes taxes & fees
Sep 20 - Sep 21
Snowarts- Game room, Fireplace, Close to golf!
Terrace/patio

11. 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 CA $1,049
CA $1,969 total
includes taxes & fees
Sep 20 - Sep 21
150 acres of serenity in Barnard VT new to vrbo, check our reviews elsewhere!
Private kitchen

12. Hot Tub Getaway - Near Killington - Sleeps 12

Hot Tub Getaway - Near Killington - Sleeps 12
Killington
The price is CA $356
CA $1,273 total
includes taxes & fees
Sep 22 - Sep 23
Hot Tub Getaway - Near Killington - Sleeps 12
Smart TV, fireplace, video games, books

13. 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 CA $286
CA $810 total
includes taxes & fees
Sep 22 - Sep 23
Authentic farmhouse for those who love cozy, quirky, historical imperfection
Smart TV, fireplace

14. 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 CA $651
CA $1,323 total
includes taxes & fees
Sep 23 - Sep 24
Alpine Chalet Grill, Fire pit, Pool, Gym, CornHole
Exterior

15. BearRight- AC, Pool, Hot Tub, Grill, FirePit

BearRight- AC, Pool, Hot Tub, Grill, FirePit
Killington
9.8 out of 10, Exceptional, (13 reviews)
"Place was perfect for us for a group ski weekend."
United States
Kevin F.
The price is CA $600
CA $1,197 total
includes taxes & fees
Sep 20 - Sep 21
BearRight- AC, Pool, Hot Tub, Grill, FirePit
Smart TV, fireplace

16. 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 CA $450
CA $930 total
includes taxes & fees
Sep 20 - Sep 21
Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna
Terrace/patio

17. Estelle Cottage- Private Sauna, Hot tub, Pool, AC

Estelle Cottage- Private Sauna, Hot tub, Pool, AC
The Woods
10.0 out of 10, Exceptional, (2 reviews)
"Yes!! King beds!! Tall people love king beds and they delivered. This does not diminish the fact that everything was excellent for our stay. From the welcome gifts including some great local coffee and syrup, to the relaxing sauna, the comfortable large living room and bedrooms, and all amenities, we wanted for nothing. Truly a gem on our whole vacation! We looked forward to returning in the late afternoon knowing we had a quiet evening and a good sleep ahead of us. Truly a great place to...
United States
Devin
The price is CA $471
CA $965 total
includes taxes & fees
Sep 21 - Sep 22
Estelle Cottage- Private Sauna, Hot tub, Pool, AC
Smart TV

18. Escape to this brand-new 3BR/2.5BA cabin just minutes from Killington Resort!

Escape to this brand-new 3BR/2.5BA cabin just minutes from Killington Resort!
Killington
10.0 out of 10, Exceptional, (1 review)
"Beautiful home made for a perfect holiday weekend"
United States
Gregg Z.
The price is CA $452
CA $863 total
includes taxes & fees
Sep 30 - Oct 1
Escape to this brand-new 3BR/2.5BA cabin just minutes from Killington Resort!
Property grounds

19. New Luxury Cabin-Sauna, Hot Tub, Arcade, King Beds

New Luxury Cabin-Sauna, Hot Tub, Arcade, King Beds
Killington
The price is CA $482
CA $1,091 total
includes taxes & fees
Sep 22 - Sep 23
New Luxury Cabin-Sauna, Hot Tub, Arcade, King Beds
Dining

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

large ski ranch hot tub close to killington pets ok
Mendon
9.0 out of 10, Wonderful, (8 reviews)
"The hot tub was great after a day of skiing."
United States
Callison A.
The price is CA $247
CA $671 total
includes taxes & fees
Sep 28 - Sep 29
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

On The River Inn

On The River Inn

8/10 Good
"Extremely quaint and love the rooms and balcony… Dining room gorgeous Wish there were Apps on the Tv for streaming… that’s all"
Marcia 2-night trip
Posted 10 hours ago
On The River Inn

Find out more about Stockbridge

Stockbridge Vacation Homes information

Number of reviews
74
Accommodation
704 Vacation Homes
Lowest Price
CA $266
Highest Price
CA $1,969

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