
Holiday rentals with outdoor seating in Stockbridge
Find and book unique rentals with outdoor seating on Airbnb
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

Private cozy 2-bedroom, short drive to town
Thank you to Leif and the family for a great stay! Leif was a fabulous host, being very helpful and responsive. His wife was also very nice and shoveled out the walk way for us. The place was just as described in the listing. Comfy beds with easy access to the ski way. Thanks Leif!

Home Sweet Home
As usual the place was nice and clean . A very comfortable and homey atmosphere and tastefully decorated! I always enjoy her places!

Sunny Sunapee Retreat (Upstairs Only)
Julie's place is so close to Mount Sunapee and the Lake! It is wonderful on the inside and has plenty of room for guests. It is also close to a couple great food options. This house is a great place to stay.

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

Rustic Charm
One of the best Airbnbs I have ever stayed in! We had a girls trip and adored staying here. HIGHLY RECOMMEND!! So clean, had everything we could need, felt at home immediately, and even better than described. Honestly loved it!

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!! 🤩

Enjoy Brand new construction in the mountains!
Beautiful ski weekend with our family. So close to Killington, Bear and Pico. Lovely place to unwind after a day on the slopes. Enjoyed the hot tub and sauna! Easy cooking in the stocked kitchen and peaceful for sleeping with cozy beds!
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
Great place to stay for skiing Sugarbush or Mad River Glen, convenient to restaurants and shops. Very quiet setting, just be prepared for a little bit of non-paved road to climb to access it. The apartment felt more spacious and open than I expected, and accommodated 3 adults quite comfortably. Wax bench was a nice bonus for us skiers!

Dog Team Falls Apartment - Minutes from Middlebury
Our stay at Sue’s well exceeded our expectations. The place was the perfect peaceful getaway. Such a beautiful spot. Upon arrival we connected our Bluetooth and immediately had our music streaming throughout the apartment. Sunlight streamed in, geese flew overhead as we stood on the deck overlooking the river. The sofa enveloped us and the fireplace just perfected it all. Sue was inviting without being intrusive and responded immediately when we reached out with questions. We hope to visit again in the near future!

Mountain View Retreat
We had a lovely stay. Everything was exactly as pictured and described. Everything you need for a weekend in VT. Highly recommend especially if visiting for an event at Middlebury College. Location is very convenient to campus and town.

Cozy Apt. Near heart of Middlebury Fiber WIFI
Perfect location for our needs during our stay in Middlebury; Hospital 5 minutes away. Equipped with 2 TV’s allowing entertainment for different tastes of types of tv shows. Clean cozy and comfortable.

"Dragonfly Apartment" Private Bristol Apartment
Very friendly host and location is in a quiet part of town. it felt very private as well. A++

Two-Bedroom apartment in the Green Mountains
Dick and Dorothy are some of the most lovely, hospitable folks we have ever met and we feel so lucky to have gotten to know them through our extended stays at their apartment for the the last 5 winters. Hancock is a truly special community and the apartment is an excellent choice for anyone looking to visit the area. It is conveniently located, well-stocked, and delightfully quaint. We are already excited to return!
Apartment rentals with outdoor seating

Renovated unit, prime location! Shuttle on/Ski off
This was our second time staying at Caitlyn’s condo in Killington, we chose it again for a reason !! The vibe of the condo is super relaxing, the decor is thoughtful and cool. The fire place makes coming back after a day on the slopes so cozy! We love coming to Killington and this condo is so close to the snowshed lot, it’s perfect!

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
This space was perfect for our family. With walking distance to the entrance of the slopes, this location was ideal for our ski getaway. I appreciated the small touches that made this experience feel luxurious, the provided coffee, wine, wood for the usable fire place. The beds were comfortable and the space was spacious. We would definitely visit Jim’s place again!

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
Very clean and great location. It was about an 8 minute walk to the Ramshead lodge and we ate at two restaurants within a 5 minute walk. The shuttle was also easy and ran frequently. Would recommend!

Okemo Clock Tower Base Ski-in/Ski-out Condo
We loved it. Although it’s not the newest or fanciest condo the location can’t be better right at the Clocktower Base. Our family of for had an amazing time snowboarding and exploring the area. Great restaurants close by and we will definitely be back next year.

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
30 properties
Nightly prices starting at
£53 before taxes and fees
Total number of reviews
2K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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- Okemo Mountain Resort
- Sugarbush Resort
- Stratton Mountain Resort
- Bolton Valley Resort
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Tenney Mountain Resort
- Cochran's Ski Area
- Country Club of Vermont
- Mount Sunapee Resort
- Dorset Field Club
- Ekwanok Country Club
- Hildene, The Lincoln Family Home
- Adirondack Extreme Adventure Course
- Bromley Mountain Ski Resort
- Killington Adventure Center
- Baker Hill Golf Club
- Whaleback Mountain
- Lake Sunapee Country Club
- Fox Run Golf Club
- Storrs Hill Ski Area
- Montshire Museum of Science
- Fort Ticonderoga
- Lincoln Peak Vineyard