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

Stockbridge Holiday Rentals

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

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, (5 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$2,001
HK$4,286 total
includes taxes & fees
8 Jul - 9 Jul
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, (3 reviews)
"Exactly as pictured, specious, clean. Owners were extremely responsive and kind."
United States
Sophie L.
The price is HK$1,113
HK$4,658 total
includes taxes & fees
7 Jul - 8 Jul
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, (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 HK$1,113
HK$4,658 total
includes taxes & fees
7 Jul - 8 Jul
Ski Home/Arcade Mountain Views Near Killington/Woodstock
Outdoor dining

Glamping hut with WiFi in Ripton, biking, hiking, skiing

Glamping hut with WiFi in Ripton, biking, hiking, skiing
Ripton
9.6 out of 10, Exceptional, (7 reviews)
"Beautiful, magical location, and prompt communication."
United States
Alex
The price is HK$698
HK$1,309 total
includes taxes & fees
5 Jul - 6 Jul
Glamping hut with WiFi in Ripton, biking, hiking, skiing
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
Chelsea
10.0 out of 10, Exceptional, (48 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$847
HK$1,124 total
includes taxes & fees
15 Jul - 16 Jul
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you
Property grounds

Secluded retreat in the trees

Secluded retreat in the trees
Roxbury
10.0 out of 10, Exceptional, (43 reviews)
"Very cozy and easy check in!"
United States
Emily R.
The price is HK$988
HK$1,924 total
includes taxes & fees
7 Jul - 8 Jul
Secluded retreat in the trees
Dining

Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (11 reviews)
"Very nice place to stay in Rutland."
United States
Dave M.
The price is HK$741
HK$1,669 total
includes taxes & fees
12 Jul - 13 Jul
Cozy Rutland Retreat
Exterior

Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley
Warren
9.2 out of 10, Wonderful, (11 reviews)
"We had a great stay - Quiet, clean, cozy, and a great location, we'll definitely stay here again for future trips!"
United States
Sloan S.
Beautiful home located in the Mad River Valley
Interior

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

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Cavendish
10.0 out of 10, Exceptional, (19 reviews)
"We had a great stay. The hot tub was perfect after a long day of skiing."
United States
Michael L.
The price is HK$1,341
HK$2,389 total
includes taxes & fees
7 Jul - 8 Jul
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Aerial view

Mountain Green

Mountain Green
2.0 star property
Killington
7.2 out of 10, Good, (26 reviews)
"I enjoy the location "
United States
troy
The price is HK$612
HK$1,829 total
includes taxes & fees
15 Jul - 16 Jul
Mountain Green
Private kitchen

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 HK$699
HK$1,802 total
includes taxes & fees
19 Jul - 20 Jul
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
TV, fireplace, DVD player, books

Resort condo with mountain views, full kitchen, and free WiFi

Resort condo with mountain views, full kitchen, and free WiFi
Killington
8.8 out of 10, Excellent, (47 reviews)
"Great location. Great amenities. Great communication. "
United States
Jason B.
The price is HK$527
HK$2,670 total
includes taxes & fees
7 Jul - 8 Jul
Resort condo with mountain views, full kitchen, and free WiFi
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, (12 reviews)
"The accommodations were very lovely. The host was friendly."
United States
Serge
The price is HK$1,372
HK$2,749 total
includes taxes & fees
30 Jul - 31 Jul
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Fridge, oven, stovetop, coffee/tea maker

Brookside Cabin - Your Vermont Offgrid Escape

Brookside Cabin - Your Vermont Offgrid Escape
Brookfield
The price is HK$1,112
HK$3,142 total
includes taxes & fees
9 Jul - 10 Jul
Brookside Cabin - Your Vermont Offgrid Escape
Fireplace, books

Stetson Hollow Cabin by Stetson Brook

Stetson Hollow Cabin by Stetson Brook
Warren
9.8 out of 10, Exceptional, (168 reviews)
"Jill was very attentive to make sure we had everything we needed very nice stay!"
United States
Kathy B.
The price is HK$1,694
HK$3,435 total
includes taxes & fees
15 Jul - 16 Jul
Stetson Hollow Cabin by Stetson Brook
Fridge, microwave, oven, stovetop

Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Leicester
10.0 out of 10, Exceptional, (81 reviews)
"Great place to stay for a Vermont getaway! "
United States
Jeremy H.
The price is HK$1,155
HK$1,777 total
includes taxes & fees
26 Jul - 27 Jul
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Property grounds

Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around

Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around
Hancock
10.0 out of 10, Exceptional, (4 reviews)
"The host was easy to communicate with, gracious and helpful. Amenities were generous and everything was in excellent condition. Really enjoyed the quiet treed setting and the hot tub."
United States
Elizabeth N.
The price is HK$1,482
HK$3,847 total
includes taxes & fees
19 Jul - 20 Jul
Cozy cabin >> Hottub, WiFi, AC. Easy access to outdoors activities year around
Interior

Trailside Village #7: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals

Trailside Village #7: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
Killington
9.4 out of 10, Exceptional, (63 reviews)
"Good place. Hosts were in touch and the hot tub was great. "
United States
Bethany S.
The price is HK$1,416
HK$4,359 total
includes taxes & fees
6 Jul - 7 Jul
Trailside Village #7: Slopeside 1BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
Interior

103 Deluxe One bedroom Queen Suite w/ outdoor heated pool

103 Deluxe One bedroom Queen Suite w/ outdoor heated pool
Killington
9.6 out of 10, Exceptional, (18 reviews)
"Would stay again!"
United States
Hannah M.
The price is HK$815
HK$1,235 total
includes taxes & fees
14 Jul - 15 Jul
103 Deluxe One bedroom Queen Suite w/ outdoor heated pool
Fridge, microwave, oven, stovetop

Dreamy Artist Chalet in Secluded Historic Village

Dreamy Artist Chalet in Secluded Historic Village
East Warren
9.6 out of 10, Exceptional, (18 reviews)
"Loved the property. Clean, modern, great location."
United States
Richard
The price is HK$1,670
HK$3,319 total
includes taxes & fees
7 Jul - 8 Jul
Dreamy Artist Chalet in Secluded Historic Village
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

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

10/10 Excellent
"This place is wonderful. Super clean. Bathroom shower/tub was so shiny. Beds clean and comfortable. Loved the full fridge with the built-in ice maker. We really enjoyed that. It was nice to have a stovetop too and the toaster. The sink even had a garbage disposal. They have frozen dinners for sale if you forget to bring your own and they sell ice cream as the fridge has the freezer. We will definitely stay there again. Best place and very reasonably priced too. My only issue was the super big/thick pillows. Luckily I did bring my own. Over all it is a really terrific place to stay. Staff was friendly and helpful. Very, very clean. I highly recommend this place."
Angelina 4-night trip
Posted 2 hours ago
My Place Hotel-Randolph VT

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 Killington Adventure Center, 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.