Stockbridge Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Stockbridge

Cozy Loft for two with Hot Tub & Mtn Views

10.0 out of 10, Exceptional, (252)
"We had the most amazing week from check in to check out! We cant wait to come back."
Cozy Loft for two with Hot Tub & Mtn Views

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (46)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Mountain Green

2.0 star property
6.6 out of 10, (10)
"The condo was very cozy for a family of four and suited us perfectly. Beds were comfortable and condo was clean. "
The price is NZ$416
includes taxes & fees
17 Aug - 18 Aug
Mountain Green

Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views

9.0 out of 10, Wonderful, (43)
"My favorite place to stay in the area. Love it! "
Amazing home on 90 acres - dog-friendly - AC, fireplace & great mountain views

Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!

9.0 out of 10, Wonderful, (53)
"There were dead bugs in the bathroom sink and bath, but it's fairly easy to clean them. Everything else in the room is great!"
The price is NZ$286
includes taxes & fees
19 Aug - 20 Aug
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!

Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

8.0 out of 10, Very good, (35)
"Convenient for skiing and visiting the greater VT area. Unit has what you need for your stay."
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts

Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

10.0 out of 10, Exceptional, (505)
"Our stay at the Vermont Cabin "Romantic Retreat" was amazing. Owner was very communicative and made our stay stress free. Even though it's listed as a romantic retreat, it was great for the family too. The cabin was well stocked with everything we needed during our stay and the hottub was definitely a hit. We cant wait for our next stay."
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

Secluded retreat in the trees

10.0 out of 10, Exceptional, (24)
"The place was great ,it fit into our budget and the owners were more than helpful."
Secluded retreat in the trees

Pristine Custom Cottage, Grand Piano, Massage Studio on Site

10.0 out of 10, Exceptional, (56)
"It was such a lovely stay. Everything was super tidy, clean, comfortable and cozy. We especially loved reading about the story of the build. Would absolutely recommend! "
The price is NZ$279
includes taxes & fees
13 Aug - 14 Aug
Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Converted Carriage Barn | The Carriage House Unit1

9.8 out of 10, Exceptional, (20)
"Charming, comfortable, beautiful place. Felt like home and was everything you could want from a converted barn in Vermont!"
Converted Carriage Barn | The Carriage House Unit1

Beautifully renovated with fireplace and coffee bar

10.0 out of 10, Exceptional, (113)
"Very cozy, great kitchen. The beds are extremely comfortable. The surrounding area is beautiful with plenty to do. Highly recommend."
Beautifully renovated with fireplace and coffee bar

Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

2.0 star property
10.0 out of 10, Exceptional, (20)
"It is not luxurious, but is absolutely unique and fun! We loved it!"
The price is NZ$263
includes taxes & fees
25 Aug - 26 Aug
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

Killington Farmhouse-Mountain Biking, Golf, Hiking

10.0 out of 10, Exceptional, (3)
"We visited in the summer…Spacious with room to spread out. Clean with all the things you need. Good communication. Laundry area a little spooky but great working laundry area."
Killington Farmhouse-Mountain Biking, Golf, Hiking

Treehouse at Wise Pines- SoBo

9.8 out of 10, Exceptional, (21)
"The treehouse is super comfortable and spacious and the lodge was very cozy with everything you need! Breakfast was great too :)"
The price is NZ$347
includes taxes & fees
23 Aug - 24 Aug
Treehouse at Wise Pines- SoBo

Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

9.8 out of 10, Exceptional, (17)
"We loved the house and especially the location. The views are beautiful and the proximity to town, the mountain and parks make it a fantastic spot to stay."
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit

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

10.0 out of 10, Exceptional, (20)
"Thanks for a great stay!"
The price is NZ$571
includes taxes & fees
19 Aug - 20 Aug
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Brand new 2021 Reno of Federal Style House, steps from Downtown Brandon

10.0 out of 10, Exceptional, (59)
"Beautiful house right in the village. Easy access to both Sugarbush and Killington. Would definitely stay here again. "
Brand new 2021 Reno of Federal Style House, steps from Downtown Brandon

Quaint lakefront home with a fire pit and beautiful views

9.4 out of 10, Exceptional, (96)
"We had a great time staying at this cabin. It’s really well located and was perfect for our stay."
Quaint lakefront home with a fire pit and beautiful views

5/2 Old Farmhome-Beautiful Valley Views-Near Skiing-Sugarbush

9.4 out of 10, Exceptional, (77)
"Great place to stay and great host!"
The price is NZ$511
includes taxes & fees
18 Aug - 19 Aug
5/2 Old Farmhome-Beautiful Valley Views-Near Skiing-Sugarbush

Treehouse at Wise Pines- NoBo

9.8 out of 10, Exceptional, (11)
"Unique settings. Loved the accommodations "
The price is NZ$345
includes taxes & fees
13 Aug - 14 Aug
Treehouse at Wise Pines- NoBo
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Stockbridge Hotel Reviews

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.