Stockbridge Holiday Rentals from €175: Search Short-Term Rentals

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Holiday Rentals in Stockbridge

"Everything was wonderful. Easy in and out. Near to almost everything. Beautiful area. I left my keys by mistake and they were wonderful in getting them back to me. I would stay there again. "

"The cabin was amazing, the design and decor is perfect and the space is perfect. The hot tub and fire pit were so lovely in the evening, and the movie theatre was also excellent for watching TV and films. Jeff was an excellent host, super friendly and helpful and the area was lovely and quiet, very peaceful. Thanks again! "

"The Cozy Loft was the perfect place to get away from everyday work and left stressors. It provided us a place to rest and relax. It was also not far from towns to explore (great hiking, restaurants, antique shopping). Would highly recommend to others traveling to that area. "

"It was a wonderful little cabin that was clean and decorated comfortably. It had everything we needed. The hot tub was delightful! "

"This was a really nice spacious property. It was very clean and in a nice location. "

"We loved the condo and the easy walking avvess to all of what Killington offers! We would definitely stay here again! "

"We loved the cabin and its proximity to the town of Woodstock. Nice to come home at the end of the day. The only issue is the bedrooms are upstairs and the bathroom is downstairs….but we managed. Overall a great stay. "

"Accurate representation of the property. Check in was easy after some confusion as the access door is right next to another unit and not wanting to interfere with another group late at night. Owners were able to clarify and said they would put a better note into the welcome message to alleviate future confusion. Overall, good price and would stay again."

"The location of the property was great.. Centrally located to everything we wanted to see. I would have liked to have a vacuum or even a broom available. The place had a few areas that could have been cleaner. "

"Cabin had everything we needed and more. We found it to be a great location for the small day trips we did to surrounding towns. Location is just gorgeous. "

includes taxes & fees

26 Nov - 27 Nov

"Great weekend! Beautiful location !!"

"Our stay at Camp Tiger Ted was so wonderful. The amount of detail and care David put into building and now maintaining the property is second to none. The house was meticulously clean and had so many charming details. David also gave us both massages in his in home studio which waA the most relaxing way to end our stay!"

includes taxes & fees

1 Dec - 2 Dec

"We were a bit disappointed with this property. The pictures are a bit misleading as it felt dark and stuffy, which we didn’t expect. There was a strong cigarette odor that was hard to adjust to and the room kept dropping down to very cold temperatures (50s) even after we adjusted the thermostat. This was stressful since we have a 15 month old and were worried about her being too cold all night. The deck was completely blocked by a mound of treacherous ice from water dripping off the roof, which...

"Very cute cabin in the woods. Less than 2 miles off of route 4, which made it easy to get anywhere in Vermont!"

"Beautiful property and wonderful host. Very welcoming and cozy, and within a quick drive of lots of great activities. I would definitely stay here again!"

includes taxes & fees

26 Nov - 27 Nov

"Many years ago my husband and I had summer access to an identical condo to this one in Solitude Village on Mt. Okemo, so this past week was a real walk down memory lane! The condo was lovely…very clean and well appointed, with sweeping views of the mountains from the master bedroom and living room. The king mattress was very comfortable, and the numerous linens available were fresh, plentiful and high-end. The grounds of Solitude were exquisitely maintained, and while these units do not have AC,...

"Great place - second time we've stayed here. Plenty of space, well-equipped chef's kitchen - great for cooking and entertaining. If you have kids or family and want to cook for them, this is the place you want. Private and cooled in the Spring/Summer by all the trees - great place to stay while visiting Queeche, Woodstock, and beyond."

"Gorgeous property with everything that we needed! It was relaxing and comfortable for everyone. The kids had a blast! The property management team was great with communication and offered early check in and late check out. Would absolutely stay here again!"

"We had a lovely time at the Arched Chalet for my family's annual vacation in Vermont. It was very comfortable, well-appointed, and in a great location. Even in the summer heat we did not need the AC - it was so comfortable with the fans and the lower level is naturally cool. Great location near Camp Plymouth (we went to the lake twice), and restaurants/shops in Ludlow and Woodstock."

"Place seemed older/dated, no a/c, my daugther's commented they heard scratching in the walls at night so may have been some type of rodent. Pots and pans were old and rough to cook with. "

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"Very friendly service."

includes taxes & fees

9 Dec - 10 Dec

"We enjoyed our stay at the Killington Mountain Lodge and would definitely recommend it! The hot tub is awesome, the food/drinks served are good, the staff is super friendly, and the hotel itself was really nice. Super convenient location for skiing too. "

includes taxes & fees

3 Dec - 4 Dec

"Kind and friendly staff, free snacks and well kept rooms."

includes taxes & fees

1 Dec - 2 Dec

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 €175 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.

Recent reviews of Stockbridge properties

5/5 Excellent

"Very friendly service."

A verified traveller stayed at Comfort Inn Trolley Square

Posted 22 hours ago

Killington Mountain Lodge, Tapestry Collection by Hilton

5/5 Excellent

"We enjoyed our stay at the Killington Mountain Lodge and would definitely recommend it! The hot tub is awesome, the food/drinks served are good, the staff is super friendly, and the hotel itself was really nice. Super convenient location for skiing too. "

A verified traveller stayed at Killington Mountain Lodge, Tapestry Collection by Hilton

Posted 1 day ago

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 Pico Peak. Killington Resort and Pico Mountain at Killington Ski Resort are a couple of places you'll find in the wider area.

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.

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Holiday Rentals in Stockbridge

Check Stockbridge holiday rental availability

Holiday Rentals in Stockbridge

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

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

Cozy Loft for two with Hot Tub

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

Beautiful Myrtle Beach Condo with Amenities Galore

Ski-in/ski-out condo with W/D, indoor pool, & hot tub

Cozy 1850s home on the riverfront with mountain & river views - dog-friendly

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

Trail Creek 33 | Condo in Killington

Stetson Hollow Cabin by Stetson Brook

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly

Pristine Custom Cottage, Grand Piano, Massage Studio on Site

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

Dog-friendly cabin with forest setting, woodstove & deck - near Killington

Treehouse at Wise Pines- SoBo

Ski-in/out condo with pool, 2 hot tubs, sauna - short walk to Solitude clubhouse

Luxe Quechee home on quiet road - chef’s kitchen, two-car garage, screened porch

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo

Charming, dog-friendly home with a private sauna, full kitchen, & furnished deck

Other types of properties in Stockbridge you may be interested in

Comfort Inn Rutland - Killington

Killington Mountain Lodge, Tapestry Collection by Hilton

Hampton Inn White River Junction

Find out more about Stockbridge

Recent reviews of Stockbridge properties

Comfort Inn Trolley Square

Killington Mountain Lodge, Tapestry Collection by Hilton

Align Inn Vermont

White River Inn and Suites

Mountain Sports Inn

The Mountain Inn at Killington

Hampton Inn White River Junction

Brandon Inn

Woodstock Inn & Resort

Frequently asked questions