Holiday Rentals in Stockbridge

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Our top choices for Stockbridge holiday 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.
The price is €418
includes taxes & fees
20 Apr - 21 Apr
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, (3 reviews)
"Exactly as pictured, specious, clean. Owners were extremely responsive and kind."
United States
Sophie L.
The price is €496
includes taxes & fees
19 Apr - 20 Apr
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, (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 €496
includes taxes & fees
19 Apr - 20 Apr
Ski Home/Arcade Mountain Views Near Killington/Woodstock

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, (4 reviews)
"All was so nice. The bed the coziness the cleanliness the location. "
United States
Sara B.
The price is €145
includes taxes & fees
17 Apr - 18 Apr
Glamping hut with WiFi in Ripton, biking, hiking, skiing

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, (8 reviews)
"The accommodations were very lovely. The host was friendly."
United States
Serge
The price is €241
includes taxes & fees
19 Apr - 20 Apr
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

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, (17 reviews)
"It was an amazing experience! "
United States
Gruha
The price is €246
includes taxes & fees
20 Apr - 21 Apr
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

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, (42 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 €150
includes taxes & fees
17 Apr - 18 Apr
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

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, (35 reviews)
"Great location, so well set up with many extra touches inside "
United States
Victoria H.
The price is €246
includes taxes & fees
17 Apr - 18 Apr
Luxury Cabin #3 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

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, (14 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 €246
includes taxes & fees
19 Apr - 20 Apr
Luxury Cabin #1 Hot Tub, Kayaks, Paddle Boards, Private Fire Pit

Vermont Double Queen Suite | 10 Mins to Killington

Vermont Double Queen Suite | 10 Mins to Killington
Bridgewater
8.8 out of 10, Excellent, (5 reviews)
"This was perfect for our girls weekend! Great location, spacious & clean. Our host was so responsive & kind- highly recommend staying here when you visit Salem! "
United States
Brianna L.
The price is €166
includes taxes & fees
21 Apr - 22 Apr
Vermont Double Queen Suite | 10 Mins to Killington

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 €207
includes taxes & fees
19 Apr - 20 Apr
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

Secluded retreat in the trees

Secluded retreat in the trees
Roxbury
10.0 out of 10, Exceptional, (41 reviews)
"We had a great time staying in this house. For our family, it was comfortable, clean and bright and had everything we needed. "
United States
David R.
The price is €204
includes taxes & fees
23 Apr - 24 Apr
Secluded retreat in the trees

Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym

Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym
Killington
10.0 out of 10, Exceptional, (14 reviews)
"Host was very responsive and the home was great! "
United States
Rebecca B.
The price is €232
includes taxes & fees
19 Apr - 20 Apr
Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym

Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Leicester
10.0 out of 10, Exceptional, (74 reviews)
"Great place to stay for a Vermont getaway! "
United States
Jeremy H.
The price is €156
includes taxes & fees
22 Apr - 23 Apr
Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Comfortable mountain gem with pool, mountain views, & indoor parking space

Comfortable mountain gem with pool, mountain views, & indoor parking space
Killington
8.4 out of 10, Very good, (36 reviews)
"Property was just as advertised. Shuttle to the mountain is only a short 2-3 ride. The spa area was amazing. "
United States
Quinten M.
The price is €238
includes taxes & fees
19 Apr - 20 Apr
Comfortable mountain gem with pool, mountain views, & indoor parking space

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
9.0 out of 10, Wonderful, (15 reviews)
"The apartment was very comfortable, including a very convenient bathroom. There was everything we needed. Though the apartment did not look like the photo on the internet site. There was no street number on the building which made it difficult to find it. "
United States
lilya l.
The price is €211
includes taxes & fees
17 Apr - 18 Apr
5th-floor mountain-view condo, easy access to the slopes free shuttle or walk

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.
The price is €165
includes taxes & fees
22 Apr - 23 Apr
Vermont Suite | 10 Min to Woodstock & Killington

Resort condo with mountain views, full kitchen, and free WiFi

Resort condo with mountain views, full kitchen, and free WiFi
Killington
8.8 out of 10, Excellent, (46 reviews)
"Very close to Killington and in the shuttle route."
United States
Craig C.
The price is €290
includes taxes & fees
20 Apr - 21 Apr
Resort condo with mountain views, full kitchen, and free WiFi

Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (7 reviews)
"Very nice place to stay in Rutland."
United States
Dave M.
The price is €162
includes taxes & fees
21 Apr - 22 Apr
Cozy Rutland Retreat

Stetson Hollow Cabin by Stetson Brook

Stetson Hollow Cabin by Stetson Brook
Warren
9.8 out of 10, Exceptional, (167 reviews)
"Highly recommend. It was the coziest cabin and in great location. We loved having a fire each night after skiing. Perfect pet friendly lodging. "
United States
Leah V.
The price is €375
includes taxes & fees
17 Apr - 18 Apr
Stetson Hollow Cabin by Stetson Brook
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 holiday rentals

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

Stockbridge holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Stockbridge holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Stockbridge holiday rentals we have selected for you start as low as €204 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Stockbridge rentals

At Expedia, we put the best Stockbridge holiday 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 holiday.

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 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 12 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.