Stockbridge Vacation Rentals

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Dec 26 - Dec 28
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Vacation Rentals in Stockbridge

Dining
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.
$458 nightly
The price is $483
Dec 10 - Dec 11
Total with taxes and fees
Gnome Home Mountain Ski Chalet w/Sauna Killington
Property grounds
Ski home/Pool Table Mountain Views near Killington/Woodstock

Ski home/Pool Table Mountain Views near Killington/Woodstock

Stockbridge
10.0 out of 10, Exceptional, (2)
"Exactly as pictured, specious, clean. Owners were extremely responsive and kind."
United States
Sophie L.
$582 nightly
The price is $652
Dec 9 - Dec 10
Total with taxes and fees
Ski home/Pool Table Mountain Views near Killington/Woodstock
Terrace/patio
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
8.0 out of 10, Very Good, (1)
"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.
$824 nightly
The price is $923
Dec 10 - Dec 11
Total with taxes and fees
Spacious Vermont Mountain Retreat | 4BR/4BA | Near Killington & Hiking | Perfect for Groups
Terrace/patio
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.
$533 nightly
The price is $597
Dec 9 - Dec 10
Total with taxes and fees
Ski Home/Arcade Mountain Views Near Killington/Woodstock
Property grounds
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, (36)
"Lovely farm and friendly hosts"
United States
Ruilin
$140 nightly
The price is $157
Dec 13 - Dec 14
Total with taxes and fees
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you
Property grounds
Treehouse at Wise Pines- SoBo

Treehouse at Wise Pines- SoBo

Woodstock
9.8 out of 10, Exceptional, (24)
"What a unique experience staying in a literal tree house. The bathroom shared with the other tree house was so wonderfully built as is the barn that it resides in. I only stayed one night and wished I stayed multiple nights. I will definitely consider staying here again for future MTB trips in the area! "
United States
Taku S.
$171 nightly
The price is $187
Dec 9 - Dec 10
Total with taxes and fees
Treehouse at Wise Pines- SoBo
Interior
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, (10)
"Super easy check in, beautiful and peaceful. Will def be back "
United States
Tyler S.
$292 nightly
The price is $318
Dec 9 - Dec 10
Total with taxes and fees
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Property grounds
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.
$233 nightly
The price is $261
Dec 9 - Dec 10
Total with taxes and fees
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Exterior
Secluded retreat in the trees

Secluded retreat in the trees

Roxbury
10.0 out of 10, Exceptional, (36)
"Absolutely beautiful! So pleased with everything about our stay!"
United States
Gwen B.
$212 nightly
The price is $237
Dec 9 - Dec 10
Total with taxes and fees
Secluded retreat in the trees
House (2 Bedrooms) | Interior
Ludlow Ski Cabin 2 Mi to Ski Parking

Ludlow Ski Cabin 2 Mi to Ski Parking

3.0 star property
Ludlow
$333 nightly
The price is $366
Dec 9 - Dec 10
Total with taxes and fees
Ludlow Ski Cabin 2 Mi to Ski Parking
Beach
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.
$490 nightly
The price is $549
Dec 10 - Dec 11
Total with taxes and fees
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
Exterior
Treehouse at Wise Pines- NoBo

Treehouse at Wise Pines- NoBo

Woodstock
9.8 out of 10, Exceptional, (13)
"Unique settings. Loved the accommodations "
United States
Gabriela
$171 nightly
The price is $187
Dec 10 - Dec 11
Total with taxes and fees
Treehouse at Wise Pines- NoBo
Interior
Beautiful home offering privacy on 7 acres with private pond

Beautiful home offering privacy on 7 acres with private pond

West Windsor
10.0 out of 10, Exceptional, (30)
"Very relaxing house, we all enjoyed the fireplaces and pellet stove and the well-equipped kitchen allowed us to cook beautiful meals. The property is gorgeous and neighbors are far away. This was the perfect place for a friends reunion/ski trip!"
United States
Roy S.
Beautiful home offering privacy on 7 acres with private pond
Exterior detail
Ben & Jerry Suite | Skiing | Hiking | Biking

Ben & Jerry Suite | Skiing | Hiking | Biking

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
$189 nightly
The price is $207
Dec 9 - Dec 10
Total with taxes and fees
Ben & Jerry Suite | Skiing | Hiking | Biking
Terrace/patio
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

Bridgewater
9.6 out of 10, Exceptional, (17)
"Very nice home! Plenty of room for everyone and a short drive to the mountain! Perfect "
United States
Gerri B.
$482 nightly
The price is $540
Dec 10 - Dec 11
Total with taxes and fees
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit
Indoor pool
Mountain Green

Mountain Green

2.0 star property
Killington
7.0 out of 10, Good, (15)
"Great communication from Jeff."
United States
Dennis
$240 nightly
The price is $264
Dec 9 - Dec 10
Total with taxes and fees
Mountain Green
Exterior
Spacious country home, beautiful sunsets, 40 acres

Spacious country home, beautiful sunsets, 40 acres

Tunbridge
9.8 out of 10, Exceptional, (43)
"The accommodations were great with plenty of room. We all wanted to lay on the living room couches because they were so comfortable! The property was nice and peaceful with lots of flowers, bushes and trees to observe."
United States
Karen P.
$406 nightly
The price is $455
Dec 9 - Dec 10
Total with taxes and fees
Spacious country home, beautiful sunsets, 40 acres
Fridge, microwave, dishwasher, coffee/tea maker
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, (63)
"Condo well equipped- hosts very responsive-pool area great! "
United States
gail m.
$225 nightly
The price is $254
Dec 9 - Dec 10
Total with taxes and fees
Snowshed & Ramshead Ski Lodges in walking distance plus shuttle service
Interior
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Cavendish
10.0 out of 10, Exceptional, (30)
"Beautiful property and excellent accommodations"
United States
Anthony W.
$304 nightly
The price is $331
Dec 9 - Dec 10
Total with taxes and fees
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Exterior
Killington Blue Studio: Sleeps 4, Close to Mtn 123

Killington Blue Studio: Sleeps 4, Close to Mtn 123

Killington
9.4 out of 10, Exceptional, (9)
"Great location and clean property"
United States
KEVIN C.
$231 nightly
The price is $261
Dec 15 - Dec 16
Total with taxes and fees
Killington Blue Studio: Sleeps 4, Close to Mtn 123
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

North Star Lodge and Resort

North Star Lodge and Resort

10/10 Excellent
"Location is very convenient. Service as described online."
Yilun 2-night trip
Posted 2 days ago
North Star Lodge and Resort

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 $157 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.

Explore a world of travel with Expedia

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.