
Holiday rentals with outdoor seating in Stockbridge
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Top-rated rentals with outdoor seating in Stockbridge
Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.
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Popular amenities for outdoor seating rentals in Stockbridge
House rentals with outdoor seating

Home Sweet Home
Perfect for a ski weekend with friends. Easy drive to Killington. Comfortably fit the six of us and had a ton of space to chill and relax on the couches after a long ski day! Definitely recommend!

Stay by the Mettawee
The house is absolutely stunning! We loved how clean and well organized everything is. We did a ski trip with a bunch of friends. And this house is conveniently located between two resorts: Okemo and Killington. Some of us had Epic pass and some - Icon. This was a perfect solution. Beverly was very responsive and caring. We felt right at home. The only small inconvenience is - that there is no dish washing machine. I know we became so spoiled with the technology. We easily solved by making a rule that everyone washes after themselves. Just something to note. This is absolutely not a deal breaker for me. Love the house! Would definitely come back and recommend to friends!

Launch Pad
Stayed here for a few days at Killington. Peaceful neighborhood would recommend if you’re looking for a place to crash.

Grange Hall, South Woodstock Historic Home
We have the loveliest time and can’t wait to return. Thank you for being so helpful and responsive

Quiet lakeside retreat with private dock.
This is a lovely place for a get-away time. It's very comfortably furnished, spotless, and in a beautiful area. The kitchen is one of the most adequately equipped of any Airbnb place we have stayed in. The hosts are super responsive and helpful!

Historic Home on 17 acres of land. Go escape!
Staying here is always a joy for the entire family! It has become an annual tradition that we all look forward to in winter. Thank you for being so accommodating with our schedule and a special thanks to Mitchell for going the extra mile to snow blow a waking path for me and the dogs to keep our daily routine of visiting the horses, after the last storm brought over 13” of snow. P.S. the new stove/oven is amazing!! 🤩

10 min to Mtn Hot tub & Sauna! Ski, Bike, & Board!
Alan's place worked great for our ski weekend at Killington and he was a very proactive and reponsive host to communicate with. The house is new and beautifully decorated--very comfortable and cozy!!

Eastman Luxury Retreat Dartmouth College /Sunapee
This was a great spot for our family to enjoy a ski trip to Mount Sunapee. We loved the views of the surrounding forest and the house was extremely clean and comfortable. The beds were super comfy and the zoned heating kept us toasty on some very cold nights! Helder was friendly and very quick to reply to any questions.
Apartment rentals with outdoor seating

River's Bend NEW 1-bd Apt - 8 Mins to Montpelier
We had a very comfortable stay. The setting on the river was quite peaceful, and the home was comfortable. It was a quick drive to Norwich University to watch hockey and visit our daughter, also a quick drive into Montpelier. The kitchen is well stocked for cooking meals in, and we enjoyed setting the puzzle. We will definitely stay again when we come back for another visit.

Lovely 2 Bedroom Apartment w/deck & pond view
This rental was perfect for our family’s overnight ski trip to Okemo. We have two teenaged sons who shared a bedroom. The kitchen had everything we needed to cook breakfast and (most importantly) to meet the AM caffeine needs. The rental was approximately 10 minutes away from Okemo, which was the best part for us. Already planning next February’s ski trip!

Mad River Valley Ski Cabin
A Cozy and clean apartment in the mountains nearby to skiing. Katelyn gave useful instructions for getting in and the place looked just like the photos. The dishwasher worked great and there were enough pots and utensils for me to cook meals. A few things to keep in mind: It is on a mountain so you need an AWD vehicle during the winter or mud season, but with one I had no problem at all. It is also underneath a house, so you can hear footsteps or voices from upstairs. This didn’t bother me since I live in an apartment building, but something to know if you’re not used to that.

Dog Team Falls Apartment - Minutes from Middlebury
We had an absolutely phenomenal stay at Sue’s place. We met her husband as well, and he was so kind and helpful. It was accurately described, very clean, and she was very responsive. We were impressed with how much light the apartment let in the middle of winter. The backyard views were incredible. It was an absolutely perfect stay for what we needed. We visited the college and were only five minutes from the campus. The town is very cute with everything we needed right there at our fingertips. We would 10 out of 10 highly recommend and come back at any time of year. This is a property that would be beautiful during every season.

Mountain View Retreat
We had such a great time staying at Andrew's place in Middlebury. Lovely little guest house with amazing windows and a great view of the snowy plains behind the house. Peaceful location, lots of amenities, really close to town!

Cozy Apt. Near heart of Middlebury Fiber WIFI
Benjamin’s Airbnb was so cozy and clean and great little home away from home. He is friendly and responsive and I can’t wait to stay at one of his airbnbs again!

Charming & Peaceful Upper Valley 1BR Retreat
Cheryl’s place was exactly as described. It was the perfect size for me and my significant other. It was perfectly centralized from nearby towns. Cheryl was very responsive and gave us recommendations if we wanted to go exploring. We do wish that we came in a different season where there wasn’t snow, so we can explore the property, but otherwise everything was perfect! We definitely recommend her listing!

"Dragonfly Apartment" Private Bristol Apartment
Thank you, Kelly, for a great stay at your place! This was the perfect, budget-friendly location for the 3 of us with access to near-by ski areas. Very comfy bedding on the bed, plenty of plush towels, hairdryer, and well-equipped kitchen that allowed us save money on dinners. Easy parking and entry. Felt very safe in the area and with deadbolts on the doors. My boys and I had a great time and would love to come back soon!
Apartment rentals with outdoor seating

Renovated unit, prime location! Shuttle on/Ski off
Great location, 5 mins from Snowshed lodge. The pull out bed was perfect for our kids to share (12 & 9). The place was well updated, not perfect but great for the three day ski trip we were on. The only downside was that the dishwasher didn't work so we had to do chores on vacation that we don't even do at home and the walls are thin, but the other families respected the quiet time from 10pm-7am which was nice. Otherwise, this place is a gem. Caitlyn was very responsive and checked in to make sure things were going well throughout our trip. We'll definitely be back.

Cozy Light-filled Condo in Charming Eastman
Perfect spot for our family holiday get together. Very quiet and relaxing visit. Lyn was a terrific host and went above and beyond to be sure we had no problems with our stay.

⭐️Cozy Ski On/Ski Off 2-Bed/Bath w/Fireplace
James was a great host, the place was very clean and VERY close the the ski trail. Would love to stay again some day!

TWO BEDROOM RENOVATED MOUNTAIN VIEW CONDO
Extremely nice cabin, very recently renovated. The owner has a keen eye for organization, everything is neatly placed where it should be. Linens are clean, beds were super comfortable. Amazing stay, thank you Cathy

Location + Spa! - Cozy 2BR Condo - Mountain Side
Emmy’s place was perfect for a ski weekend at Killington! Well stocked, good location, and she was super responsive.

Okemo Clock Tower Base Ski-in/Ski-out Condo
We stayed here for 3 nights and had a great experience. Perfect location for our entensions. Will definitely be back!

Ski, Ride, Walk On/Off Condo On Pico at Killington
Great location for pico mountain. The ski on ski off was pretty easy to find and nicely located. The location is slightly less ideal for killington, as you need to take a shuttle that has multiple stops. We also ended up on a bigger bus to take us back from Killington and the drop off was on the main road, which was a bit difficult to walk on in our snow gear. Overall, nice apartment and perfect for my group of friends.

Modest Mountain Dacha
Very comfortable stay - convenient to ski wither Sugarbush or Mad River. Philip sent specific instructions for turning the heat up on arrival. It took a little while to warm up, but individual thermostats in LR and BR worked nicely. Local recommendations for restaurants and such were spot on.
Quick stats about holiday rentals with outdoor seating in Stockbridge
Total rentals
50 properties
Nightly prices starting at
£55 before taxes and fees
Total number of reviews
3.1K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
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