Stockbridge Holiday Rentals

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Check prices for these dates

In two weeks
6 Feb - 8 Feb
In two months
20 Mar - 22 Mar
In three months
17 Apr - 19 Apr
In four months
15 May - 17 May

Our top choices for Stockbridge holiday rentals

Property grounds

Gnome Home Mountain Ski Chalet w/Sauna Killington

Gnome Home Mountain Ski Chalet w/Sauna Killington
Stockbridge
10.0 out of 10, Exceptional, (4 reviews)
"Nice property in a beautiful location. Host was very responsive and informative. Thanks for the stay!"
United States
Gerald S.
The price is HK$2,247
HK$4,585 total
includes taxes & fees
2 Feb - 3 Feb
Gnome Home Mountain Ski Chalet w/Sauna Killington
Exterior

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, (2 reviews)
"Exactly as pictured, specious, clean. Owners were extremely responsive and kind."
United States
Sophie L.
The price is HK$1,380
HK$4,886 total
includes taxes & fees
26 Jan - 27 Jan
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Interior

Ski Home/Arcade Mountain Views Near Killington/Woodstock

Ski Home/Arcade Mountain Views Near Killington/Woodstock
Stockbridge
10.0 out of 10, Exceptional, (2 reviews)
"Skied Killington for 2 days and was a 20 min drive. Fun to drive the 100."
United States
Kevin M.
The price is HK$1,380
HK$4,886 total
includes taxes & fees
26 Jan - 27 Jan
Ski Home/Arcade Mountain Views Near Killington/Woodstock
4 bedrooms, free WiFi, bed sheets

Spacious Vermont Mountain Retreat | 4BR/4BA | Near Killington & Hiking | Perfect for Groups

Spacious Vermont Mountain Retreat | 4BR/4BA | Near Killington & Hiking | Perfect for Groups
Stockbridge
8.0 out of 10, Very good, (1 review)
"Would like to have had a tv in all the bedrooms. The back yard needed mowed. Other than that it was a good stay. Nice place"
United States
Troy H.
The price is HK$2,843
HK$7,956 total
includes taxes & fees
25 Jan - 26 Jan
Spacious Vermont Mountain Retreat | 4BR/4BA | Near Killington & Hiking | Perfect for Groups
Exterior

Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you
2.0 star property
Chelsea
10.0 out of 10, Exceptional, (39 reviews)
"Lovely farm and friendly hosts"
United States
Ruilin
The price is HK$1,170
HK$1,502 total
includes taxes & fees
26 Jan - 27 Jan
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you
Property grounds

Treehouse at Wise Pines- NoBo

Treehouse at Wise Pines- NoBo
Woodstock
9.6 out of 10, Exceptional, (15 reviews)
"The treehouse was so cool and well maintained. We were very warm and everything was clearly laid out for where to go, where to park, etc. "
United States
Ethan
The price is HK$1,170
HK$1,467 total
includes taxes & fees
26 Jan - 27 Jan
Treehouse at Wise Pines- NoBo
Interior

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
2.0 star property
Cavendish
10.0 out of 10, Exceptional, (11 reviews)
"Super easy check in, beautiful and peaceful. Will def be back "
United States
Tyler S.
The price is HK$1,565
HK$2,670 total
includes taxes & fees
26 Jan - 27 Jan
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Interior

The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
2.0 star property
Mendon
9.8 out of 10, Exceptional, (11 reviews)
"Great place! Secluded but close to everything. We will definitely stay again."
United States
Patricia Y.
The price is HK$1,112
HK$3,413 total
includes taxes & fees
26 Jan - 27 Jan
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
Terrace/patio

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Sharon
10.0 out of 10, Exceptional, (6 reviews)
"Cabin was spotless and exactly what I expected"
United States
mark g.
The price is HK$1,223
HK$2,531 total
includes taxes & fees
26 Jan - 27 Jan
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Exterior

Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington

Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
2.0 star property
Plymouth
10.0 out of 10, Exceptional, (14 reviews)
"We had a great stay! Beautiful spot tucked in the woods. Great host communication!"
United States
Julie-Anne B.
The price is HK$2,340
HK$5,494 total
includes taxes & fees
9 Feb - 10 Feb
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
Property grounds

Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland

Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland
2.5 star property
Rutland
9.6 out of 10, Exceptional, (7 reviews)
The price is HK$1,170
HK$1,493 total
includes taxes & fees
10 Feb - 11 Feb
Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland
Aerial view

The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
The price is HK$877
HK$2,681 total
includes taxes & fees
2 Feb - 3 Feb
The Suites at Killington Center
Property grounds

Vermont Suite | 10 Min to Killington & Woodstock

Vermont Suite | 10 Min to Killington & Woodstock
Bridgewater
9.2 out of 10, Wonderful, (7 reviews)
"Overall, a great stay. "
United States
Meghan J.
The price is HK$764
HK$1,689 total
includes taxes & fees
26 Jan - 27 Jan
Vermont Suite | 10 Min to Killington & Woodstock
Smart TV, fireplace

Woods Resort and Spa: Cozy 2-Bedroom Condo in Killington, VT with Ski, Tennis, and Pool Access

Woods Resort and Spa: Cozy 2-Bedroom Condo in Killington, VT with Ski, Tennis, and Pool Access
2.0 star property
The Woods
10.0 out of 10, Exceptional, (3 reviews)
"We headed up to Killington for some fun spring skiing with the fam and the place was great - spacious, well appointed, and comfortable. Would definitely stay again."
United States
Ryan T.
The price is HK$1,247
HK$3,718 total
includes taxes & fees
26 Jan - 27 Jan
Woods Resort and Spa: Cozy 2-Bedroom Condo in Killington, VT with Ski, Tennis, and Pool Access
Property grounds

Treehouse at Wise Pines- SoBo

Treehouse at Wise Pines- SoBo
Woodstock
9.8 out of 10, Exceptional, (25 reviews)
"Friendly owners with a very comfortable and accommodating space.Very well thought out with a great common space .Hiking trails , fire pit , animals , fresh eggs and produce in season.Highly recommended!!"
United States
Jo-Alice S.
The price is HK$1,170
HK$1,467 total
includes taxes & fees
9 Feb - 10 Feb
Treehouse at Wise Pines- SoBo
Exterior

5th-floor mountain-view condo, easy access to the slopes free shuttle or walk

5th-floor mountain-view condo, easy access to the slopes free shuttle or walk
Killington
9.0 out of 10, Wonderful, (10 reviews)
"Great property, as advertised."
United States
Chris A.
The price is HK$952
HK$2,548 total
includes taxes & fees
25 Jan - 26 Jan
5th-floor mountain-view condo, easy access to the slopes free shuttle or walk
Fridge, microwave, oven, stovetop

Jack S`Bearo - Slopes, Fireplace, Pool.

Jack S`Bearo - Slopes, Fireplace, Pool.
Killington
10.0 out of 10, Exceptional, (14 reviews)
"My husband and i really enjoyed our stay at Jack S'bearo! Was a nice, cozy condo for a couple or a small family. Highly recommend!"
United States
Erin
The price is HK$1,044
HK$2,555 total
includes taxes & fees
27 Jan - 28 Jan
Jack S`Bearo - Slopes, Fireplace, Pool.
Indoor pool

Welcoming condo near the slopes with free WiFi and full kitchen

Welcoming condo near the slopes with free WiFi and full kitchen
Killington
7.4 out of 10, Good, (31 reviews)
"beds were comfortable"
United States
Juan T.
The price is HK$717
HK$2,613 total
includes taxes & fees
27 Jan - 28 Jan
Welcoming condo near the slopes with free WiFi and full kitchen
Property grounds

Doc's Lake house 1st floor, 2 bedroom apartment

Doc's Lake house 1st floor, 2 bedroom apartment
Salisbury
10.0 out of 10, Exceptional, (74 reviews)
"Doc runs a great place for all to enjoy. "
United States
William D.
The price is HK$1,053
HK$1,581 total
includes taxes & fees
16 Feb - 17 Feb
Doc's Lake house 1st floor, 2 bedroom apartment
Indoor pool, a heated pool

Modern Mountain Condo with Spa

Modern Mountain Condo with Spa
The Woods
9.6 out of 10, Exceptional, (10 reviews)
"The condo was perfect for the 3 of us. It was clean and well equipped. The spa was awesome, with pool, hot tub, steam room, and sauna."
United States
Kevin
Modern Mountain Condo with Spa
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

Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington

10/10 Excellent
"Clean room"
Samantha 1-night trip
Posted 2 days ago
Best Western Inn & Suites Rutland-Killington

Find out more about Stockbridge

Search for holiday rentals in Stockbridge on Expedia! You can easily find your home rentals, villas, holiday apartments in Stockbridge using one of the methods below:

  • View our selection of featured holiday rentals in Stockbridge
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  • Enter your travel dates to view the best deals on holiday rentals in Stockbridge while they last

Look no further and take a look at our great range of rental properties in Stockbridge!

Frequently asked questions

Are there holiday rentals in Stockbridge?

Yes, there are holiday rentals close to the most popular sights in Stockbridge, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Stockbridge has to offer?

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly: This holiday home rental outside of Stockbridge is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books.

How many holiday rentals are there in Stockbridge?

With 11 Expedia holiday rentals, you're guaranteed to find just the right place for your Stockbridge stay.

What’s there to see and do in Stockbridge?

While exploring the area, visit family-friendly sights like Sugarbush Farm, or get outside and enjoy nature at Green Mountain National Forest. Les Newell Wildlife Management Area and Belcher Library are other places to visit while you're in town.

What’s a holiday rental in Stockbridge like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Stockbridge. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll have everything you want. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from public hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for a small group gathering.