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

Stockbridge Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Stockbridge vacation rentals

A living room with a wooden console table, a potted plant, and two clocks. A staircase and a fireplace with a TV are in the background.

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.
$475 nightly
The price is $532
Nov 8 - Nov 9
Total with taxes and fees
Ski Home/Arcade Mountain Views Near Killington/Woodstock
Winter Wonderland

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.
$475 nightly
The price is $532
Nov 8 - Nov 9
Total with taxes and fees
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.
$457 nightly
The price is $481
Nov 8 - Nov 9
Total with taxes and fees
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.
$846 nightly
The price is $948
Nov 8 - Nov 9
Total with taxes and fees
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.
$325 nightly
The price is $367
Nov 7 - Nov 8
Total with taxes and fees
Fabulous 4-bedroom chalet in tranquil Killington getaway with Hot tub two Kings
A modern living room with a glass coffee table, a sofa, a TV mounted on the wall, a fireplace, and a blue accent wall.

6. 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.
$228 nightly
The price is $258
Nov 8 - Nov 9
Total with taxes and fees
Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington
A modern bedroom with a bed, bedside table, and a window with a view.

7. 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.
$230 nightly
The price is $260
Nov 8 - Nov 9
Total with taxes and fees
The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531
An aerial view of a residential area with houses, a swimming pool, and a parking lot.

8. 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.
$234 nightly
The price is $264
Nov 8 - Nov 9
Total with taxes and fees
Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.
A bedroom with two beds, a dresser, a window with a view of greenery, and a painting on the wall.

9. Ski Condo Close to Killington: Discounted Ski Rentals and Shuttle Bus. Killington Center 631

Ski Condo Close to Killington: Discounted Ski Rentals and Shuttle Bus. Killington Center 631
Killington
9.0 out of 10, Wonderful, (7 reviews)
"Easy, convenient location. Perfect no frills last minute ski trip. Would stay again. Good communication."
United States
Marcus G.
$223 nightly
The price is $252
Nov 8 - Nov 9
Total with taxes and fees
Ski Condo Close to Killington: Discounted Ski Rentals and Shuttle Bus. Killington Center 631
A modern kitchen with a central island, stainless steel appliances, and wooden cabinets.

10. 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.
$366 nightly
The price is $413
Nov 8 - Nov 9
Total with taxes and fees
Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532
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
$358 nightly
The price is $404
Nov 8 - Nov 9
Total with taxes and fees
The Swirl Suite at Killington: Renovated 2RM/2BA Suite. Sleeps 6. Discounted Ski Rentals.
A living room with a sofa, a dining table with chairs, a kitchen area with wooden cabinets, and a bar.

12. 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.
$282 nightly
The price is $319
Nov 8 - Nov 9
Total with taxes and fees
Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.
A modern kitchen with a microwave, stove, and red stools. A living area with a fireplace and a TV is visible in the background.

13. 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.
$379 nightly
The price is $428
Nov 8 - Nov 9
Total with taxes and fees
Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332
A ski resort with multiple buildings, a ski slope, and a mountain in the background.

14. 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.
$227 nightly
The price is $256
Nov 8 - Nov 9
Total with taxes and fees
Jack S`Bearo - Slopes, Fireplace, Pool
A swimming pool with a hot tub, surrounded by a building with balconies and a fenced area with trees.

15. Mountain Green ground-floor condo with private yard off the patio

Mountain Green ground-floor condo with private yard off the patio
Killington
$248 nightly
The price is $280
Nov 8 - Nov 9
Total with taxes and fees
Mountain Green ground-floor condo with private yard off the patio
A spacious living room with a fireplace, a television, and a large window.

16. 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.
$598 nightly
The price is $676
Nov 8 - Nov 9
Total with taxes and fees
4BR Killington Home Perfect for Families, Pet-Friendly
A rustic interior with a stone fireplace, wooden beams, leather furniture, and a balcony with a view.

17. Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything

Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
Killington
10.0 out of 10, Exceptional, (25 reviews)
"Great place "
United States
Kathleen M.
$430 nightly
The price is $486
Nov 9 - Nov 10
Total with taxes and fees
Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything
A modern two-story building with a wooden facade, large windows, and a covered porch with seating.

18. Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins
3.0 star property
Windsor
9.8 out of 10, Exceptional, (15 reviews)
"This property was extremely beautiful and peaceful. Loved being able to walk around the farm and say hi to the animals. The views of the mountains from the cabin or gorgeous, we enjoyed having our coffee on the porch each morning. Having fresh eggs and scones in our cabin upon arrival was a very nice surprise. Will definitely be staying there again."
United States
Brenda
$168 nightly
The price is $183
Nov 18 - Nov 19
Total with taxes and fees
Fat Sheep Farm & Cabins
An indoor swimming pool with a hot tub, surrounded by a forest-themed mural, and a metal ladder for access.

19. SnowCub- Pets Indoor Pool Hot Tub Sauna Fireplace

SnowCub- Pets Indoor Pool Hot Tub Sauna Fireplace
The Woods
10.0 out of 10, Exceptional, (27 reviews)
"Such a beautiful place to stay while in killington!!"
United States
Brittany R.
$346 nightly
The price is $391
Nov 9 - Nov 10
Total with taxes and fees
SnowCub- Pets Indoor Pool Hot Tub Sauna Fireplace
A living room with a sofa, coffee table, and fireplace. There is a large window and a balcony with outdoor furniture.

20. FirBear- Pool, Gym, Fireplace, Hot tub!

FirBear- Pool, Gym, Fireplace, Hot tub!
The Woods
9.8 out of 10, Exceptional, (25 reviews)
"Great place to stay for an escape to the mountains!"
United States
Kristin G.
$343 nightly
The price is $387
Nov 10 - Nov 11
Total with taxes and fees
FirBear- Pool, Gym, Fireplace, 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

On The River Inn

On The River Inn

10/10 Excellent
"We loved our spacious room, the sauna, pool/hot tub and game room! We were welcomed with a s’mores pack and spent the evening by the cozy fire pit. Lovely hotel!"
Rachel 1-night trip
Posted 11 hours ago
On The River Inn

Find out more about Stockbridge

Everything you need to know about Stockbridge vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Stockbridge vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Stockbridge vacation 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 low season months. For more hustle and bustle, you may prefer to visit Stockbridge in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $197 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Stockbridge rentals

At Expedia, we put the best Stockbridge vacation 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 vacation.

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 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?

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

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 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 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.