Stockbridge Vacation Rentals

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Our top choices for Stockbridge vacation 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 reviews)
"Nice property in a beautiful location. Host was very responsive and informative. Thanks for the stay!"
United States
Gerald S.
$541 nightly
The price is $574
Jan 13 - Jan 14
Total with taxes and fees
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 reviews)
"Exactly as pictured, specious, clean. Owners were extremely responsive and kind."
United States
Sophie L.
$560 nightly
The price is $627
Jan 12 - Jan 13
Total with taxes and fees
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 reviews)
"Skied Killington for 2 days and was a 20 min drive. Fun to drive the 100."
United States
Kevin M.
$626 nightly
The price is $701
Jan 27 - Jan 28
Total with taxes and fees
Ski Home/Arcade Mountain Views Near Killington/Woodstock

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, (39 reviews)
"Lovely farm and friendly hosts"
United States
Ruilin
$172 nightly
The price is $193
Jan 13 - Jan 14
Total with taxes and fees
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

Off Grid Glamping Shed with River Access

Off Grid Glamping Shed with River Access
2.0 star property
Randolph
10.0 out of 10, Exceptional, (1 review)
$84 nightly
The price is $94
Jan 12 - Jan 13
Total with taxes and fees
Off Grid Glamping Shed with River Access

Treehouse at Wise Pines- NoBo

Treehouse at Wise Pines- NoBo
Woodstock
9.8 out of 10, Exceptional, (14 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
$172 nightly
The price is $188
Jan 12 - Jan 13
Total with taxes and fees
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, (5 reviews)
"Cabin was spotless and exactly what I expected"
United States
mark g.
$249 nightly
The price is $279
Jan 13 - Jan 14
Total with taxes and fees
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Secluded retreat in the trees

Secluded retreat in the trees
Roxbury
10.0 out of 10, Exceptional, (39 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.
$210 nightly
The price is $235
Jan 12 - Jan 13
Total with taxes and fees
Secluded retreat in the trees

Vermont Suite | 10 Min to Woodstock & Killington

Vermont Suite | 10 Min to Woodstock & Killington
Bridgewater
10.0 out of 10, Exceptional, (5 reviews)
"We had a lovely time in Woodstock Vermont. The Bridgewater Inn was cozy and perfect for our weekend get away"
United States
Rosie L.
$224 nightly
The price is $245
Jan 14 - Jan 15
Total with taxes and fees
Vermont Suite | 10 Min to Woodstock & Killington

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 reviews)
"Super easy check in, beautiful and peaceful. Will def be back "
United States
Tyler S.
$367 nightly
The price is $402
Jan 13 - Jan 14
Total with taxes and fees
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Cozy Cabin Retreat

Cozy Cabin Retreat
Roxbury
10.0 out of 10, Exceptional, (33 reviews)
"Lovely, quiet & the BEST star gazing!!!"
United States
Jill F.
$190 nightly
The price is $213
Jan 14 - Jan 15
Total with taxes and fees
Cozy Cabin Retreat

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, (45 reviews)
"Perfect place for a long weekend"
United States
Patrick D.
$246 nightly
The price is $278
Jan 13 - Jan 14
Total with taxes and fees
Clean & bright condo with mountain views & modern kitchen - walk to lifts

Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.6 out of 10, Exceptional, (5 reviews)
"Peaceful stay in the city! We were headed to the rodeo, so this was the perfect distance away! "
United States
Aislinn F.
$168 nightly
The price is $188
Jan 13 - Jan 14
Total with taxes and fees
Cozy Rutland Retreat

Killington Ski Resort VT Vacation Condos

Killington Ski Resort VT Vacation Condos
3.5 star property
Killington
$326 nightly
The price is $367
Jan 21 - Jan 22
Total with taxes and fees
Killington Ski Resort VT Vacation Condos

Cozy condo on ski shuttle route with free WiFi & full ktichen

Cozy condo on ski shuttle route with free WiFi & full ktichen
Killington
8.4 out of 10, Very Good, (38 reviews)
"Great place. Met our needs. "
United States
Sean K.
$294 nightly
The price is $332
Jan 15 - Jan 16
Total with taxes and fees
Cozy condo on ski shuttle route with free WiFi & full ktichen

Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit
Bridgewater
9.6 out of 10, Exceptional, (17 reviews)
"Very nice home! Plenty of room for everyone and a short drive to the mountain! Perfect "
United States
Gerri B.
$516 nightly
The price is $578
Jan 12 - Jan 13
Total with taxes and fees
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service

Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service
Killington
9.4 out of 10, Exceptional, (64 reviews)
"Condo well equipped- hosts very responsive-pool area great! "
United States
gail m.
$277 nightly
The price is $313
Jan 12 - Jan 13
Total with taxes and fees
Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service

5th-floor mountain-view condo, easy access to the slopes free shuttle or walk

5th-floor mountain-view condo, easy access to the slopes free shuttle or walk
Killington
9.4 out of 10, Exceptional, (9 reviews)
"Great property, as advertised."
United States
Chris A.
$293 nightly
The price is $331
Jan 15 - Jan 16
Total with taxes and fees
5th-floor mountain-view condo, easy access to the slopes free shuttle or walk

Spa, Fireplace & Pet Friendly - Top of the Hill

Spa, Fireplace & Pet Friendly - Top of the Hill
Quechee
9.8 out of 10, Exceptional, (6 reviews)
"Appreciated the large outdoor deck area, grill, and plenty of space for the family to relax."
United States
Maryanne C.
$575 nightly
The price is $650
Jan 29 - Jan 30
Total with taxes and fees
Spa, Fireplace & Pet Friendly - Top of the Hill

Jack S`Bearo - Slopes, Fireplace, Pool.

Jack S`Bearo - Slopes, Fireplace, Pool.
Killington
10.0 out of 10, Exceptional, (13 reviews)
"My husband and i really enjoyed our stay at Jack S'bearo! Was a nice, cozy condo for a couple or a small family. Highly recommend!"
United States
Erin
$266 nightly
The price is $301
Jan 14 - Jan 15
Total with taxes and fees
Jack S`Bearo - Slopes, Fireplace, Pool.
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 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 $188 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?

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 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.