Stockbridge Vacation Rentals

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Check prices for these dates

In two weeks
Mar 13 - Mar 15
In two months
Apr 24 - Apr 26
In three months
May 22 - May 24
In four months
Jun 19 - Jun 21

Our top choices for Stockbridge vacation 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 ￥38,931
￥83,393 total
includes taxes & fees
Mar 24 - Mar 25
Gnome Home Mountain Ski Chalet w/Sauna Killington
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
9.0 out of 10, Wonderful, (2 reviews)
"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 ￥55,103
￥155,415 total
includes taxes & fees
Feb 26 - Feb 27
Spacious Vermont Mountain Retreat | 4BR/4BA | Near Killington & Hiking | Perfect for Groups
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 ￥44,819
￥122,372 total
includes taxes & fees
Mar 11 - Mar 12
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 ￥44,819
￥122,372 total
includes taxes & fees
Mar 11 - Mar 12
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
10.0 out of 10, Exceptional, (3 reviews)
"Super cute and cozy! It was perfect."
United States
Sarah D.
The price is ￥13,763
￥25,806 total
includes taxes & fees
Mar 8 - Mar 9
Glamping hut with WiFi in Ripton, biking, hiking, skiing
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, (7 reviews)
"Very welcoming, awesome weekend getaway."
United States
Zachary B.
The price is ￥19,995
￥45,444 total
includes taxes & fees
Feb 26 - Feb 27
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
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 ￥23,387
￥29,159 total
includes taxes & fees
Mar 16 - Mar 17
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
Cavendish
10.0 out of 10, Exceptional, (14 reviews)
"This was absolutely perfect. Every part of the cabin was well thought out from design to decor. We had such an amazing time and already want to plan another getaway to this place. "
United States
Adam B.
The price is ￥31,806
￥53,951 total
includes taxes & fees
Mar 24 - Mar 25
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
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, (41 reviews)
"Lovely farm and friendly hosts"
United States
Ruilin
The price is ￥23,196
￥29,790 total
includes taxes & fees
Mar 28 - Mar 29
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you
1 bedroom, iron/ironing board, travel crib, free WiFi

Cozy Cabin Retreat

Cozy Cabin Retreat
Roxbury
10.0 out of 10, Exceptional, (35 reviews)
"Lovely, quiet & the BEST star gazing!!!"
United States
Jill F.
The price is ￥18,232
￥32,890 total
includes taxes & fees
Feb 26 - Feb 27
Cozy Cabin Retreat
Property grounds

Secluded retreat in the trees

Secluded retreat in the trees
Roxbury
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 ￥19,645
￥37,194 total
includes taxes & fees
Mar 9 - Mar 10
Secluded retreat in the trees
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 ￥13,720
￥31,717 total
includes taxes & fees
Mar 9 - Mar 10
Vermont Suite | 10 Min to Killington & Woodstock
TV, fireplace

Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.

Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.
Killington
10.0 out of 10, Exceptional, (11 reviews)
"perfect setup, very clean and comfortable. "
United States
Jeremiah J.
The price is ￥27,732
￥69,450 total
includes taxes & fees
Mar 2 - Mar 3
Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.
Property grounds

Cozy Rustic Cabin, NOTE: pipes are frozen. Please don’t book now! Back soon.

Cozy Rustic Cabin, NOTE: pipes are frozen. Please don’t book now! Back soon.
Rutland
9.6 out of 10, Exceptional, (11 reviews)
"Absolutely adored our stay! The cabin was cozy and had everything we could need and the hot tub was a huge plus after a long day of snowboarding. Would definitely come back!"
United States
Erin M.
The price is ￥23,196
￥29,790 total
includes taxes & fees
Mar 26 - Mar 27
Cozy Rustic Cabin, NOTE: pipes are frozen. Please don’t book now! Back soon.
1 bedroom, desk, iron/ironing board, free WiFi

Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington

Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington
Killington
9.6 out of 10, Exceptional, (4 reviews)
"The place was clean and easy to get to. "
United States
Sarah Z.
The price is ￥23,934
￥56,660 total
includes taxes & fees
Feb 26 - Feb 27
Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington
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 ￥20,112
￥43,480 total
includes taxes & fees
Mar 8 - Mar 9
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Property grounds

Comfortable mountain gem with pool, mountain views, & indoor parking space

Comfortable mountain gem with pool, mountain views, & indoor parking space
Killington
8.4 out of 10, Very Good, (35 reviews)
"Great stay!"
United States
Bryann F.
The price is ￥13,408
￥48,606 total
includes taxes & fees
Mar 2 - Mar 3
Comfortable mountain gem with pool, mountain views, & indoor parking space
Fireplace, books

Stetson Hollow Cabin by Stetson Brook

Stetson Hollow Cabin by Stetson Brook
Warren
9.8 out of 10, Exceptional, (162 reviews)
"The cabin location was ideal for us , very convenient to outings and very cozy in a gorgeous setting . "
United States
judy c.
The price is ￥33,402
￥66,161 total
includes taxes & fees
Mar 10 - Mar 11
Stetson Hollow Cabin by Stetson Brook
Fridge, microwave, oven, stovetop

Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
Killington
9.0 out of 10, Wonderful, (2 reviews)
"Comfortable stay, great location. "
United States
Marjana
The price is ￥24,322
￥57,322 total
includes taxes & fees
Mar 24 - Mar 25
Luxury Condo Tucked in the Heart of Killington
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 ￥23,387
￥29,159 total
includes taxes & fees
Mar 16 - Mar 17
Treehouse at Wise Pines- SoBo
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

Holiday Inn Express Hotel & Suites White River Junction by IHG

Holiday Inn Express Hotel & Suites White River Junction by IHG

10/10 Excellent
"The rooms were clean. We used a handicap room. It met our needs. A good breakwas available too"
Daniel 2-night trip
Posted 3 days ago
Holiday Inn Express Hotel & Suites White River Junction by IHG

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!

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Frequently asked questions

Are there vacation rentals in Stockbridge?

Yes, we give you a choice of vacation rentals near the most popular sights in Stockbridge, or you can select a more remote option if you want a relaxing place to stay.

What's the top vacation rental that Stockbridge has to offer?

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly: Visitors like this Stockbridge vacation home rental. It is located on a lake and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books.

How many vacation rentals are there in Stockbridge?

With 11 Expedia vacation rentals, you're sure 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 vacation rental in Stockbridge like?

A vacation rental is a private property where you can stay for several days or longer in Stockbridge. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from public hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for a family getaway.