Stockbridge Holiday Rentals

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Our top choices for Stockbridge holiday rentals

Gnome Home Mountain Ski Chalet w/Sauna Killington

Gnome Home Mountain Ski Chalet w/Sauna Killington
Stockbridge
10.0 out of 10, Exceptional, (4)
"Nice property in a beautiful location. Host was very responsive and informative. Thanks for the stay!"
United States
Gerald S.
The price is NZ$1,011
includes taxes & fees
12 Jan - 13 Jan 2026
Gnome Home Mountain Ski Chalet w/Sauna Killington

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)
"Exactly as pictured, specious, clean. Owners were extremely responsive and kind."
United States
Sophie L.
The price is NZ$1,205
includes taxes & fees
5 Jan - 6 Jan 2026
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock

Ski Home/Arcade Mountain Views Near Killington/Woodstock

Ski Home/Arcade Mountain Views Near Killington/Woodstock
Stockbridge
10.0 out of 10, Exceptional, (2)
"Skied Killington for 2 days and was a 20 min drive. Fun to drive the 100."
United States
Kevin M.
The price is NZ$1,205
includes taxes & fees
5 Jan - 6 Jan 2026
Ski Home/Arcade Mountain Views Near Killington/Woodstock

Robert Frost Mountain Cabins

Robert Frost Mountain Cabins
3.5 star property
Ripton
10.0 out of 10, Exceptional, (40)
"Ammazing,would go again!"
United States
Joseph
The price is NZ$513
includes taxes & fees
4 Jan - 5 Jan 2026
Robert Frost Mountain Cabins

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)
"Really enjoyed the setup at the location and the owners were very responsive to any queries!"
United States
Ed N.
The price is NZ$1,124
includes taxes & fees
20 Jan - 21 Jan 2026
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington

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, (38)
"Lovely farm and friendly hosts"
United States
Ruilin
The price is NZ$330
includes taxes & fees
30 Jan - 31 Jan 2026
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

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)
"Super easy check in, beautiful and peaceful. Will def be back "
United States
Tyler S.
The price is NZ$698
includes taxes & fees
12 Jan - 13 Jan 2026
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Mountain Green

Mountain Green
2.0 star property
Killington
6.8 out of 10, (17)
"Great communication from Jeff."
United States
Dennis
The price is NZ$492
includes taxes & fees
12 Jan - 13 Jan 2026
Mountain Green

Secluded retreat in the trees

Secluded retreat in the trees
Roxbury
10.0 out of 10, Exceptional, (38)
"Absolutely beautiful! So pleased with everything about our stay!"
United States
Gwen B.
The price is NZ$405
includes taxes & fees
5 Jan - 6 Jan 2026
Secluded retreat in the trees

Treehouse at Wise Pines- NoBo

Treehouse at Wise Pines- NoBo
Woodstock
9.8 out of 10, Exceptional, (14)
"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 NZ$322
includes taxes & fees
7 Jan - 8 Jan 2026
Treehouse at Wise Pines- NoBo

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, (3)
"Very welcoming, awesome weekend getaway."
United States
Zachary B.
The price is NZ$476
includes taxes & fees
13 Jan - 14 Jan 2026
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
The price is NZ$791
includes taxes & fees
14 Jan - 15 Jan 2026
The Suites at Killington Center

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
9.2 out of 10, Wonderful, (5)
The price is NZ$332
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy Rustic Cabin, Mountain Views, Hot Tub, Fire Pit in Rutland

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)
"Great place! Secluded but close to everything. We will definitely stay again."
United States
Patricia Y.
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

Cozy Cabin Retreat

Cozy Cabin Retreat
Roxbury
10.0 out of 10, Exceptional, (33)
"A wonderful cabin. I need to come back sometime."
United States
Fletcher F.
The price is NZ$366
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy Cabin Retreat

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)
"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 NZ$484
includes taxes & fees
4 Jan - 5 Jan 2026
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

Ben & Jerry’s Studio | 10 Min to Killington

Ben & Jerry’s Studio | 10 Min to Killington
Bridgewater
9.2 out of 10, Wonderful, (7)
"Close to Woodstock and market. Easy check in. Very quiet. Kurig, no cups for coffee."
United States
Nancy
The price is NZ$380
includes taxes & fees
12 Jan - 13 Jan 2026
Ben & Jerry’s Studio | 10 Min to Killington

Beautiful home located in the Mad River Valley

Beautiful home located in the Mad River Valley
Warren
10.0 out of 10, Exceptional, (23)
"Fantastic house in a beautiful setting. Just right for the area and the kind of trip we were hoping to have. Colin is a great host as well."
United States
kevin m.
Beautiful home located in the Mad River Valley

Big Boulder at Killington – 2 Miles to Killington Base with Hot Tub, Sauna, and Views

Big Boulder at Killington – 2 Miles to Killington Base with Hot Tub, Sauna, and Views
2.0 star property
Killington
10.0 out of 10, Exceptional, (47)
"We had a great day here! The location could not be beat… Fast access to the mountain as well as restaurants on the access road. House was exactly as described, lots of space for our two family group. Would definitely rent again!"
United States
Anne P.
The price is NZ$1,827
includes taxes & fees
19 Jan - 20 Jan 2026
Big Boulder at Killington – 2 Miles to Killington Base with Hot Tub, Sauna, and Views

Clean & bright condo with mountain views & modern kitchen - walk to lifts

Clean & bright condo with mountain views & modern kitchen - walk to lifts
Killington
7.2 out of 10, Good, (44)
"Perfect place for a long weekend"
United States
Patrick D.
The price is NZ$489
includes taxes & fees
12 Jan - 13 Jan 2026
Clean & bright condo with mountain views & modern kitchen - walk to lifts
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

Find out more about Stockbridge

Everything you need to know about Stockbridge holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Stockbridge holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Stockbridge holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Stockbridge holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Stockbridge. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Stockbridge holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Stockbridge holiday rentals we have selected for you start as low as NZ$322 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Stockbridge rentals

At Expedia, we put the best Stockbridge holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Stockbridge rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Stockbridge holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Stockbridge. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.