Stockbridge Holiday Rentals

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Check prices for these dates

In two weeks
3 Apr - 5 Apr
In two months
15 May - 17 May
In three months
12 Jun - 14 Jun
In four months
10 Jul - 12 Jul

Our top choices for Stockbridge holiday rentals

Property grounds

Chalet in Stockbridge

Gnome Home Mountain Ski Chalet w/Sauna Killington
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$1,957
HK$4,227 total
includes taxes & fees
13 Apr - 14 Apr
Gnome Home Mountain Ski Chalet w/Sauna Killington
4 bedrooms, free WiFi, bed sheets

Cabin in Stockbridge

Spacious Vermont Mountain Retreat | 4BR/4BA | Near Killington & Hiking | Perfect for Groups
9.0 out of 10, Wonderful, (2 reviews)
"The host was very responsive! The house was very clean when we came and had everything we needed."
United States
Angela W.
Spacious Vermont Mountain Retreat | 4BR/4BA | Near Killington & Hiking | Perfect for Groups
Interior

Holiday Home in Stockbridge

Ski Home/Arcade Mountain Views Near Killington/Woodstock
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.
Ski Home/Arcade Mountain Views Near Killington/Woodstock
Exterior

Holiday Home in Stockbridge

Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
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$1,491
HK$5,114 total
includes taxes & fees
22 Mar - 23 Mar
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Outdoor dining

Camping in Ripton

Glamping hut with WiFi in Ripton, biking, hiking, skiing
10.0 out of 10, Exceptional, (4 reviews)
"All was so nice. The bed the coziness the cleanliness the location. "
United States
Sara B.
The price is HK$697
HK$1,308 total
includes taxes & fees
31 Mar - 1 Apr
Glamping hut with WiFi in Ripton, biking, hiking, skiing
Property grounds

Cabin in Woodstock

Treehouse at Wise Pines- NoBo
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$1,176
HK$1,475 total
includes taxes & fees
23 Mar - 24 Mar
Treehouse at Wise Pines- NoBo
Exterior

Holiday Home in Chelsea

Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you
10.0 out of 10, Exceptional, (41 reviews)
"Everything was wonderful and both hosts are very inviting owners friendly always there if you needed anything we can't wait to go back loved it "
United States
Susan K.
The price is HK$1,175
HK$1,501 total
includes taxes & fees
24 Mar - 25 Mar
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you
Terrace/patio

Cabin in Sharon

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
10.0 out of 10, Exceptional, (8 reviews)
"The accommodations were very lovely. The host was friendly."
United States
Serge
The price is HK$931
HK$2,184 total
includes taxes & fees
23 Mar - 24 Mar
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Interior

Cabin in Cavendish

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
10.0 out of 10, Exceptional, (15 reviews)
"Hot tub was wonderful! We only opened it half way for the two of us and it maintained 102-103 the entire time and was very clean! "
United States
Crissi C.
The price is HK$1,372
HK$2,440 total
includes taxes & fees
14 Apr - 15 Apr
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Aerial view

Condo in Killington

The Suites at Killington Center
3.5 star property
The price is HK$1,010
HK$2,835 total
includes taxes & fees
23 Mar - 24 Mar
The Suites at Killington Center
Property grounds

Apartment in Bridgewater

Vermont Double Queen Suite | 10 Mins to Killington
8.8 out of 10, Excellent, (5 reviews)
"This was perfect for our girls weekend! Great location, spacious & clean. Our host was so responsive & kind- highly recommend staying here when you visit Salem! "
United States
Brianna L.
The price is HK$737
HK$1,654 total
includes taxes & fees
15 Apr - 16 Apr
Vermont Double Queen Suite | 10 Mins to Killington
Property grounds

Cabin in Roxbury

Secluded retreat in the trees
10.0 out of 10, Exceptional, (41 reviews)
"Wonderful location and property. Hosts were welcoming and we had a comfortable stay. Hannah shared a bunch of local recommendations and tips! We had a great getaway!"
United States
Niti P.
The price is HK$1,102
HK$1,998 total
includes taxes & fees
1 Apr - 2 Apr
Secluded retreat in the trees
1 bedroom, iron/ironing board, travel cot, free WiFi

Cottage in Roxbury

Cozy Cabin Retreat
10.0 out of 10, Exceptional, (35 reviews)
"Lovely, quiet & the BEST star gazing!!!"
United States
Jill F.
Cozy Cabin Retreat
Outdoor dining

Apartment in Jackson Gore Base Area

Okemo | Studio Condo + Loft | Near Slopes + Pool
10.0 out of 10, Exceptional, (2 reviews)
"Very conveinent check in, nice property."
United States
michael
The price is HK$1,747
HK$2,206 total
includes taxes & fees
12 Apr - 13 Apr
Okemo | Studio Condo + Loft | Near Slopes + Pool
Aerial view

Condo resort in Killington

Mountain Green
2.0 star property
7.0 out of 10, Good, (22 reviews)
"Older unit but very convenient for the slopes, and nice to have a bar/grill in the building."
United States
Neil
The price is HK$1,377
HK$1,848 total
includes taxes & fees
12 Apr - 13 Apr
Mountain Green
Property grounds

Cabin in Woodstock

Treehouse at Wise Pines- SoBo
9.8 out of 10, Exceptional, (25 reviews)
"The treehouse was so comfortable! Every area was clean and documented well. Chelsey was great for the small amount of time that we did talk to her. Will definitely stay again. "
United States
Jennifer P.
The price is HK$1,176
HK$1,475 total
includes taxes & fees
23 Mar - 24 Mar
Treehouse at Wise Pines- SoBo
Indoor pool

Condo in Killington

Mountain view condo with full kitchen and free WiFi
7.6 out of 10, Good, (40 reviews)
"Clean, comfortable, full kitchen, fast internet, plenty of parking, great location right by the Killington base lodges. Would definitely stay here again."
United States
Brian B.
The price is HK$1,074
HK$2,722 total
includes taxes & fees
22 Mar - 23 Mar
Mountain view condo with full kitchen and free WiFi
Exterior

Condo in Killington

Trailside Village #1: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
9.4 out of 10, Exceptional, (58 reviews)
"Wonderful location…"
United States
David C.
The price is HK$1,759
HK$4,809 total
includes taxes & fees
24 Mar - 25 Mar
Trailside Village #1: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
Private kitchen

Holiday Home in Mendon

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
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 HK$776
HK$1,896 total
includes taxes & fees
26 Mar - 27 Mar
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Interior

Apartment in Killington

103 Deluxe One bedroom Queen Suite w/ outdoor heated pool
9.6 out of 10, Exceptional, (17 reviews)
"Would stay again!"
United States
Hannah M.
The price is HK$1,422
HK$2,044 total
includes taxes & fees
29 Mar - 30 Mar
103 Deluxe One bedroom Queen Suite w/ outdoor heated pool
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

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

10/10 Excellent
"always kind people "
Jacob 2-night trip
Posted 9 hours ago
Days Inn by Wyndham Rutland/Killington Area

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
  • Use the map to find apartments and other holiday homes in the Stockbridge neighbourhood you prefer
  • 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 10 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.