Stockbridge Vacation Rentals

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Check prices for these dates

In two weeks
Jun 19 - Jun 21
In two months
Jul 31 - Aug 2
In three months
Aug 28 - Aug 30
In four months
Sep 25 - Sep 27

Our top choices for Stockbridge vacation rentals

Property grounds

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.
The price is ￥35,530
￥80,198 total
includes taxes & fees
Jun 17 - Jun 18
Gnome Home Mountain Ski Chalet w/Sauna Killington
Exterior

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 ￥22,707
￥94,462 total
includes taxes & fees
Jun 7 - Jun 8
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Interior

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 ￥22,707
￥94,462 total
includes taxes & fees
Jun 7 - Jun 8
Ski Home/Arcade Mountain Views Near Killington/Woodstock
Outdoor dining

Glamping hut with WiFi in Ripton, biking, hiking, skiing

Glamping hut with WiFi in Ripton, biking, hiking, skiing
Ripton
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful, magical location, and prompt communication."
United States
Alex
The price is ￥14,231
￥26,684 total
includes taxes & fees
Jun 8 - Jun 9
Glamping hut with WiFi in Ripton, biking, hiking, skiing
Exterior

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
Chelsea
10.0 out of 10, Exceptional, (46 reviews)
"Everything was wonderful and both hosts are very inviting owners friendly always there if you needed anything we can't wait to go back loved it "
United States
Susan K.
The price is ￥17,269
￥22,923 total
includes taxes & fees
Jun 21 - Jun 22
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you
Outdoor dining

Unique Vacation Rental in an Old Farmhouse in Windsor County, Vermont

Unique Vacation Rental in an Old Farmhouse in Windsor County, Vermont
South Royalton
The price is ￥20,723
￥24,305 total
includes taxes & fees
Jun 7 - Jun 8
Unique Vacation Rental in an Old Farmhouse in Windsor County, Vermont
Interior

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Cavendish
10.0 out of 10, Exceptional, (18 reviews)
"We really enjoyed our stay! It was close to Okemo and it was so nice to relax in the hot tub after a day of skiing. We would definitely stay here again! "
United States
Dana C.
The price is ￥26,048
￥47,256 total
includes taxes & fees
Jun 7 - Jun 8
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
Property grounds

Secluded retreat in the trees

Secluded retreat in the trees
Roxbury
10.0 out of 10, Exceptional, (43 reviews)
"Great place…absolutely loved it! Clean, well appointed, and very helpful and friendly host. We plan on staying here again!"
United States
Jules
The price is ￥20,579
￥39,524 total
includes taxes & fees
Jun 15 - Jun 16
Secluded retreat in the trees
Terrace/patio

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, (11 reviews)
"The accommodations were very lovely. The host was friendly."
United States
Serge
The price is ￥19,748
￥45,580 total
includes taxes & fees
Jun 8 - Jun 9
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Property grounds

Historic Converted Concrib Glamping Cabin in the Heart of Vermont, Perfect for a Weekend Retreat in Nature

Historic Converted Concrib Glamping Cabin in the Heart of Vermont, Perfect for a Weekend Retreat in Nature
South Royalton
The price is ￥37,992
￥44,081 total
includes taxes & fees
Jun 12 - Jun 13
Historic Converted Concrib Glamping Cabin in the Heart of Vermont, Perfect for a Weekend Retreat in Nature
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, (37 reviews)
"Great location, so well set up with many extra touches inside "
United States
Victoria H.
The price is ￥26,048
￥47,256 total
includes taxes & fees
Jun 7 - Jun 8
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Interior

The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
Mendon
9.8 out of 10, Exceptional, (17 reviews)
"We wish there had been a recycle box. Also, mini split in living room didn’t work as well as the bedroom mini splits did for heat. Also, curtains/drapes on living room windows would be great and would help with heat loss."
United States
Jane
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
Smart TV, fireplace, video games, books

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Mt Holly
9.8 out of 10, Exceptional, (41 reviews)
"This house has great hang out space and plenty of space for a big family!"
United States
Cheri V.
The price is ￥23,753
￥81,065 total
includes taxes & fees
Jun 8 - Jun 9
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Fireplace, books

Stetson Hollow Cabin by Stetson Brook

Stetson Hollow Cabin by Stetson Brook
Warren
9.8 out of 10, Exceptional, (167 reviews)
"Perfect spot for our 3 day ski trip. Very nice and cozy cabin! Quiet area and the owners were great with making sure all was good. "
United States
Jeffrey C.
The price is ￥34,538
￥70,560 total
includes taxes & fees
Jun 5 - Jun 6
Stetson Hollow Cabin by Stetson Brook
Interior

Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Cavendish
10.0 out of 10, Exceptional, (15 reviews)
"Beautiful property, quiet and peaceful location. Enjoyed the access to the hot tub, and loved having a private fire pit."
United States
David V.
The price is ￥25,904
￥47,094 total
includes taxes & fees
Jun 9 - Jun 10
Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit
Interior

103 Deluxe One bedroom Queen Suite w/ outdoor heated pool

103 Deluxe One bedroom Queen Suite w/ outdoor heated pool
Killington
9.6 out of 10, Exceptional, (18 reviews)
"Would stay again!"
United States
Hannah M.
The price is ￥16,622
￥25,170 total
includes taxes & fees
Jun 9 - Jun 10
103 Deluxe One bedroom Queen Suite w/ outdoor heated pool
Dining

Hot Tub|Firepit|Pets|Near Hiking, Lake & Okemo

Hot Tub|Firepit|Pets|Near Hiking, Lake & Okemo
Plymouth
Hot Tub|Firepit|Pets|Near Hiking, Lake & Okemo
Dining

Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (8 reviews)
"Very nice place to stay in Rutland."
United States
Dave M.
The price is ￥12,232
￥30,234 total
includes taxes & fees
Jun 7 - Jun 8
Cozy Rutland Retreat
Private kitchen

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Mendon
9.8 out of 10, Exceptional, (6 reviews)
"Very pretty property, wish we could have spent more time there. Getting in and out was easy and there were plenty of options for food in town just a few minutes away. Great stay."
United States
Aurore H.
The price is ￥20,627
￥44,593 total
includes taxes & fees
Jun 15 - Jun 16
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
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

Align Inn Vermont

Align Inn Vermont

10/10 Excellent
"Beautiful area."
Laura 2-night trip
Posted less than an hour ago
Align Inn Vermont

Find out more about Stockbridge

Search for holiday rentals in Stockbridge on Expedia! You can easily find your home rentals, villas, holiday apartments in Stockbridge using one of the methods below:

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Look no further and take a look at our great range of rental properties in Stockbridge!

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 12 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.