Stockbridge Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Stockbridge holiday rentals

A wooden deck with Adirondack chairs and a table, overlooking a mountainous landscape.

1. 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 AU$795
includes taxes & fees
12 Nov - 13 Nov
Ski Home/Arcade Mountain Views Near Killington/Woodstock
A wooden deck with Adirondack chairs and a table, overlooking a mountainous landscape.

2. 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 AU$795
includes taxes & fees
12 Nov - 13 Nov
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
A rustic cabin with a wooden deck, surrounded by dense greenery and a rocky landscape.

3. Gnome Home Mountain Ski Chalet w/Sauna Killington

Gnome Home Mountain Ski Chalet w/Sauna Killington
Stockbridge
10.0 out of 10, Exceptional, (7 reviews)
"Nice property in a beautiful location. Host was very responsive and informative. Thanks for the stay!"
United States
Gerald S.
The price is AU$663
includes taxes & fees
16 Nov - 17 Nov
Gnome Home Mountain Ski Chalet w/Sauna Killington
A rustic attic bedroom with exposed wooden beams, a sloped ceiling, and a large window providing natural light.

4. 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)
"The host was very responsive! The house was very clean when we came and had everything we needed."
United States
Angela W.
The price is AU$1,419
includes taxes & fees
12 Nov - 13 Nov
Spacious Vermont Mountain Retreat | 4BR/4BA | Near Killington & Hiking | Perfect for Groups
A two-story building with a dark brown exterior, a covered porch, and a number '303' sign.

5. Fabulous 4-bedroom chalet in tranquil Killington getaway with Hot tub two Kings

Fabulous 4-bedroom chalet in tranquil Killington getaway with Hot tub two Kings
North Sherburne
8.0 out of 10, Very good, (17 reviews)
"We had a great time!"
United States
Matthew R.
The price is AU$753
includes taxes & fees
18 Nov - 19 Nov
Fabulous 4-bedroom chalet in tranquil Killington getaway with Hot tub two Kings
A spacious living room with a fireplace, a television, and a large window.

6. 4BR Killington Home Perfect for Families, Pet-Friendly

4BR Killington Home Perfect for Families, Pet-Friendly
North Sherburne
10.0 out of 10, Exceptional, (24 reviews)
"Our group had a wonderful ski weekend at the house! It was well stocked with everything we needed and the fireplace was perfect to relax near after a day on the slopes. "
United States
Christina V.
The price is AU$1,022
includes taxes & fees
12 Nov - 13 Nov
4BR Killington Home Perfect for Families, Pet-Friendly
A modern kitchen with a central island, stainless steel appliances, and wooden cabinets.

7. Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532

Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532
Killington
9.6 out of 10, Exceptional, (73 reviews)
"Cozy space close to the mountain. Host was very responsive and check in and check out was easy. "
United States
Spencer P.
The price is AU$613
includes taxes & fees
12 Nov - 13 Nov
Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532
A modern kitchen with a microwave, stove, and red stools. A living area with a fireplace and a TV is visible in the background.

8. Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332

Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332
Killington
9.4 out of 10, Exceptional, (12 reviews)
"Quick trip but would stay here again"
United States
John O.
The price is AU$634
includes taxes & fees
12 Nov - 13 Nov
Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332
A modern kitchen with stainless steel appliances, a dining area with a glass table, and a living room with a fireplace.

9. Killington Center 632: a spacious 2RM/2BA condo in the heart of Killington. Discounted ski rentals.

Killington Center 632: a spacious 2RM/2BA condo in the heart of Killington. Discounted ski rentals.
Killington
9.6 out of 10, Exceptional, (7 reviews)
"Everything was as advertised. Host was responsive to questions. Great stay overall."
United States
Riley T.
The price is AU$585
includes taxes & fees
12 Nov - 13 Nov
Killington Center 632: a spacious 2RM/2BA condo in the heart of Killington. Discounted ski rentals.
A modern bedroom with a bed, bedside table, and a window with a view.

10. The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531

The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531
Killington
9.6 out of 10, Exceptional, (5 reviews)
"Place was great"
United States
Nathan H.
The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531
A modern kitchen with white cabinets, a built-in microwave, and a stainless steel refrigerator.

11. The Swirl Suite at Killington: Renovated 2RM/2BA Suite. Sleeps 6. Discounted Ski Rentals.

The Swirl Suite at Killington: Renovated 2RM/2BA Suite. Sleeps 6. Discounted Ski Rentals.
Killington
9.2 out of 10, Wonderful, (10 reviews)
"Perfect clean space, very comfortable and great location for the week. We were not big fans of the mattress toppers, they kept sliding off, but that is a personal preference matter. Staff communication was 10 out of 10. Highly recommend."
United States
Lisa
The price is AU$599
includes taxes & fees
12 Nov - 13 Nov
The Swirl Suite at Killington: Renovated 2RM/2BA Suite. Sleeps 6. Discounted Ski Rentals.
A bedroom with a bed, two bedside tables with lamps, a wall-mounted air conditioner, and two framed pictures on the wall.

12. The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
The price is AU$679
includes taxes & fees
23 Nov - 24 Nov
The Suites at Killington Center
An aerial view of a residential area with houses, a swimming pool, and a parking lot.

13. Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.

Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
Killington
9.4 out of 10, Exceptional, (10 reviews)
"Beautiful place . My sister was visiting USA/ Vermont for the first time . We went to the Breakfast cafe next door it was amazing . "
United States
Asad B.
The price is AU$396
includes taxes & fees
12 Nov - 13 Nov
Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
A living room with a sofa, a dining table with chairs, a kitchen area with wooden cabinets, and a bar.

14. 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
9.8 out of 10, Exceptional, (14 reviews)
"We had such a great time staying here. It was clean, cozy and so convenient to walk right out the door to the slopes! "
United States
Susanne B.
The price is AU$476
includes taxes & fees
12 Nov - 13 Nov
Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.
A modern living room with a fireplace, a large sectional sofa, and a television mounted above the fireplace.

15. CubsCorner - Pool, Sauna, Gym, Close to Mountain!

CubsCorner - Pool, Sauna, Gym, Close to Mountain!
Killington
10.0 out of 10, Exceptional, (6 reviews)
"Great location with access to both Pico and Killington Mountains!"
United States
Olaf G.
The price is AU$633
includes taxes & fees
12 Nov - 13 Nov
CubsCorner - Pool, Sauna, Gym, Close to Mountain!
A modern living room with a glass coffee table, a sofa, a TV mounted on the wall, a fireplace, and a blue accent wall.

16. 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, (5 reviews)
"Great room!"
United States
Carla M.
The price is AU$389
includes taxes & fees
12 Nov - 13 Nov
Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington
A ski resort with multiple buildings, a ski slope, and a mountain in the background.

17. Jack S`Bearo - Slopes, Fireplace, Pool

Jack S`Bearo - Slopes, Fireplace, Pool
Killington
10.0 out of 10, Exceptional, (17 reviews)
"Great condo and building. Everything in excellent condition. Convenient location."
United States
Joseph S.
The price is AU$382
includes taxes & fees
12 Nov - 13 Nov
Jack S`Bearo - Slopes, Fireplace, Pool
Pass snacks across the counter without leaving the conversation in the main room.

18. Trailside Loft at Pico | Ski-In/Out Condo w/ Loft + 2BR | Steps to Lift

Trailside Loft at Pico | Ski-In/Out Condo w/ Loft + 2BR | Steps to Lift
Killington
10.0 out of 10, Exceptional, (3 reviews)
"Great midweek ski vacation. Easily walked to the slope to get to the kiosk for our ticket. Kitchen had all that we needed. "
United States
Casey C.
The price is AU$853
includes taxes & fees
12 Nov - 13 Nov
Trailside Loft at Pico | Ski-In/Out Condo w/ Loft + 2BR | Steps to Lift
A modern kitchen with granite countertops, a stainless steel sink, and a dining area with a table and chairs.

19. Gorgeous 2BR/2BA Woods Condo: Pool, Hot Tub, Spa/ Discounted Ski Rentals. V5

Gorgeous 2BR/2BA Woods Condo: Pool, Hot Tub, Spa/ Discounted Ski Rentals. V5
The Woods
10.0 out of 10, Exceptional, (15 reviews)
"Amazing location, great kitchen, my kids loved the hot tub, and it was a super easy process checking in and out. Will be staying here again!"
United States
Keaton S.
Gorgeous 2BR/2BA Woods Condo: Pool, Hot Tub, Spa/ Discounted Ski Rentals. V5
A cozy living room with a fireplace, a television, and a view of a snowy deck.

20. Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.

Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.
Killington
9.8 out of 10, Exceptional, (59 reviews)
"It was a great stay with the family!!"
United States
Mary C.
The price is AU$1,071
includes taxes & fees
12 Nov - 13 Nov
Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.
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

A stone fireplace with a sign above it reading "Trailside Lodge."
The Trailside Inn

The Trailside Inn

The Trailside Inn
North Sherburne

8/10 Good

Lovely lodge style accommodation, nestled in the snow, away from street / noise but close enough to town, restaurants...and snow fields!!
Australia
Tony
Reviewed January 23, 2017
The Trailside Inn

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 favourite 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 depend 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 AU$381 per night. Entering your travel dates in the search wizard might find you 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?

Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you: This holiday home rental outside of Stockbridge offers a garden, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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.