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, (39)
"Amazing house great price but note that there are only two split units cooling down the house which means one bed room only gets ac if the other bedrooms split unit is on and both doors are open"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
10.0 out of 10, Exceptional, (473)
"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! "
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
Cozy Loft for two with Hot Tub
10.0 out of 10, Exceptional, (219)
"Very clean , everything we needed and more , beautiful hot tub , very cozy cabin nicely decorated "
Cozy Loft for two with Hot Tub
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
9.8 out of 10, Exceptional, (195)
"The cabin is perfect for a relaxing Vermont experience. The hot tub was perfect and the area is so beautiful and quiet. We loved the large kitchen area and the quaint living room. 10/10 experience. "
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Beautiful Myrtle Beach Condo with Amenities Galore
8.8 out of 10, Excellent, (161)
"This was a really nice spacious property. It was very clean and in a nice location. "
Beautiful Myrtle Beach Condo with Amenities Galore
Ski-in/ski-out condo with W/D, indoor pool, & hot tub
9.0 out of 10, Wonderful, (18)
"We loved the condo and the easy walking avvess to all of what Killington offers! We would definitely stay here again! "
Ski-in/ski-out condo with W/D, indoor pool, & hot tub
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
9.2 out of 10, Wonderful, (15)
"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. "
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!
8.8 out of 10, Excellent, (39)
"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."
Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!
Trail Creek 33 | Condo in Killington
9.8 out of 10, Exceptional, (20)
"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. "
Trail Creek 33 | Condo in Killington
Stetson Hollow Cabin by Stetson Brook
9.8 out of 10, Exceptional, (134)
"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. "
The price is AU$730
includes taxes & fees
17 Nov - 18 Nov
Stetson Hollow Cabin by Stetson Brook
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
9.6 out of 10, Exceptional, (34)
"Great weekend! Beautiful location !!"
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
10.0 out of 10, Exceptional, (48)
"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!"
The price is AU$280
includes taxes & fees
18 Nov - 19 Nov
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts
8.4 out of 10, Very good, (25)
"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...
Cozy studio with balcony, full kitchen, and free WiFi - walk to lifts
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
8.8 out of 10, Excellent, (18)
"Very cute cabin in the woods. Less than 2 miles off of route 4, which made it easy to get anywhere in Vermont!"
Dog-friendly cabin with forest setting, woodstove & deck - near Killington
Treehouse at Wise Pines- SoBo
9.8 out of 10, Exceptional, (18)
"A cozy cabin retreat right outside of Woodstock. This was within distance to all restaurants and attractions with accessible trails right at your doorstep! "
The price is AU$280
includes taxes & fees
17 Nov - 18 Nov
Treehouse at Wise Pines- SoBo
Ski-in/out condo with pool, 2 hot tubs, sauna - short walk to Solitude clubhouse
9.2 out of 10, Wonderful, (19)
"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,...
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
8.6 out of 10, Excellent, (12)
"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."
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
9.8 out of 10, Exceptional, (18)
"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!"
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
9.8 out of 10, Exceptional, (30)
"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."
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
Charming, dog-friendly home with a private sauna, full kitchen, & furnished deck
9.6 out of 10, Exceptional, (61)
"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. "
Charming, dog-friendly home with a private sauna, full kitchen, & furnished deck
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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Other types of properties in Stockbridge you may be interested in

Comfort Inn Trolley Square
2.5 star property
8.0 out of 10, Very good, (1004)
"Staff helpful and friendly. Rooms small, but space is used efficiently. Rooms were clean and welcoming. There is occasional noise from the mechanics of the building (e.g. HVAC). A bit outside of town, probably a 20 minute walk to city center. I was comfortable, felt safe, and would stay there again if in the area."
The price is AU$176
includes taxes & fees
1 Dec - 2 Dec
Comfort Inn Trolley Square
Killington Mountain Lodge, Tapestry Collection by Hilton
3.5 star property
7.2 out of 10, Good, (1000)
"Great experience! It was a lot of fun around the pool table or the fire pit outside. We loved it! It was great to have our dog with us everywhere around the hotel. Everything is very clean and in modern design. The only downside was that the restaurant dinner menu is limited to 5 options and there is no breakfast, just a Starbucks kiosk with coffee and muffins. We will go back! "
The price is AU$250
includes taxes & fees
22 Nov - 23 Nov
Killington Mountain Lodge, Tapestry Collection by Hilton
Hampton Inn White River Junction
2.5 star property
8.4 out of 10, Very good, (1004)
"So convenient to highway, but quiet area. Desk people were so helpful"
The price is AU$201
includes taxes & fees
17 Nov - 18 Nov
Hampton Inn White River Junction
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.

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?

Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge: 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 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

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.