Stockbridge Holiday Rentals

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Holiday Rentals in Stockbridge

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3.0 star property
9.0 out of 10, Wonderful, (51)
"Clean and beautiful scenery "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Mountain Green
2.0 star property
6.6 out of 10, (13)
"Great communication from Jeff."
The price is AU$383
includes taxes & fees
19 Oct - 20 Oct
Mountain Green
Cozy Loft for two with Hot Tub & Mtn Views
10.0 out of 10, Exceptional, (264)
"Great location, marvelous host, terrific property! I'll be returning for sure!"
Cozy Loft for two with Hot Tub & Mtn Views
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
10.0 out of 10, Exceptional, (517)
"We just love the quiet and beauty of the area. We love to come here because our hosts very easy to communicate and enjoy being on vacation."
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
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, (27)
"Lovely farm and friendly hosts"
The price is AU$245
includes taxes & fees
4 Nov - 5 Nov
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you
Killington Retreat
2.0 star property
9.6 out of 10, Exceptional, (14)
"Had a great time staying so close to Killington. Sauna, hot tub and pool were a great way to warm up after a day of skiing."
Killington Retreat
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
10.0 out of 10, Exceptional, (63)
"Very clean, cozy environment. Property owner was very nice and helped with any questions we had. 100% would book again!!"
The price is AU$259
includes taxes & fees
16 Oct - 17 Oct
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen
10.0 out of 10, Exceptional, (113)
"Clean and great location!"
Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen
Cozy Cabin, Mountain Views, Hot Tub, Pool, Basketball Court, Fire Pit in Rutland
2.5 star property
The price is AU$297
includes taxes & fees
16 Oct - 17 Oct
Cozy Cabin, Mountain Views, Hot Tub, Pool, Basketball Court, Fire Pit in Rutland
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!
9.0 out of 10, Wonderful, (58)
"Great spot! And we truly appreciated the fan!"
The price is AU$264
includes taxes & fees
20 Oct - 21 Oct
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!
Beautifully renovated with fireplace and coffee bar
10.0 out of 10, Exceptional, (121)
"This place was quite simply brilliant. I stay with my wife and four kids. The kids range in age from 10-17 and we had a great stay exploring the Upper Valley area"
Beautifully renovated with fireplace and coffee bar
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
9.6 out of 10, Exceptional, (18)
"The house, its location, and dock are real nice. Would come here again."
Renovated lakefront cottage w/ hot tub, dock, kayaks, swim platform, & firepit
Killington Sapphire
9.2 out of 10, Wonderful, (7)
"Everything we needed to enjoy your family trip!"
Killington Sapphire
Spacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking
9.4 out of 10, Exceptional, (124)
"Another fun time at this well located, well appointed home."
Spacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking
Killington Vermont Ski and Snowmobiling House
9.2 out of 10, Wonderful, (44)
"Spacious and nice location. The home met our needs. Basic home with some necessities lacking like soap, shampoo, washcloths, and paper towels. Coffee maker did not function well. Cooking utensils could use an upgrade. Needs a thorough cleaning and we noticed this right away upon arrival. Hot tub did not seem to work. No air conditioning, which should be clearly noted in the property description."
Killington Vermont Ski and Snowmobiling House
Stetson Hollow Cabin by Stetson Brook
9.8 out of 10, Exceptional, (157)
"Close to everything - downtown Warren/Waitsfield, swimming, and biking trails. Perfect space for the weekend. "
The price is AU$682
includes taxes & fees
26 Oct - 27 Oct
Stetson Hollow Cabin by Stetson Brook
Amazing home on 90 acres - AC, fireplace & great mountain views
9.0 out of 10, Wonderful, (43)
"Was good older log cabin with decent amenities. Everything worked. family was comfortable. nice area."
Amazing home on 90 acres - AC, fireplace & great mountain views
Idyllic Lakefront House Suited Two Families
9.6 out of 10, Exceptional, (171)
"We spent 11 nights at the house, everything was great."
Idyllic Lakefront House Suited Two Families
Glamping hut with WiFi in Ripton, biking, hiking, skiing
The price is AU$259
includes taxes & fees
16 Oct - 17 Oct
Glamping hut with WiFi in Ripton, biking, hiking, skiing
Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!
9.8 out of 10, Exceptional, (37)
"This house was a great setting for a large group of adults and kids; plenty of room to spread out and places for everyone to sleep. Close enough to swimming holes and breweries during the day, and our sunset bonfires had a great view. It was really helpful that essentials were already at the house, and it was clean. Communication with the host was top notch!"
Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!
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, 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 favourite 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 depend 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 AU$245 per night. Entering your travel dates in the search wizard might find you 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 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.