
Vacation rentals with outdoor seating in Stockbridge
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Top-rated outdoor seating rentals in Stockbridge
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House rentals with outdoor seating

Luxury Condo Tucked in the Heart of Killington
We really enjoyed our stay at this super cute Airbnb! The location was perfect — just a quick drive to everywhere we wanted to go, which made exploring the area super convenient. The space itself was clean, cozy, and had such a charming vibe. One thing to note is that there’s no AC, which I didn’t realize ahead of time. It wasn’t a dealbreaker by any means, but as a cold sleeper, it was a bit warm for me in June — just something to keep in mind depending on the season. Overall, it was a lovely place and a great spot for a getaway!

Romantic Mountain Getaway
Thank you, Bianca, for a wonderful stay in your stylish, clean, comfortable home and beautiful property. We would definitely rate it five stars and highly recommend it to others. An extra thank you for accommodating our unplanned family graduation dinner—it meant a lot to us! Sergey and Taya

Cozy Bow House Perched in Trees w/ Hot Tub & View
This place was exactly what we were hoping for — clean, peaceful, and just as described in the listing. The space was beautifully designed, with thoughtful touches throughout, and everything was in great condition. It felt cozy and inviting from the moment we arrived. Communication with the host was smooth and easy, and check-in was a breeze. No surprises — just a really great stay in a beautiful part of Vermont. I’d absolutely come back again.

Comfortable 3 Bedroom King size Master w/ En suite
We had a wonderful time making s'mores on the fire pit, playing pool, and relaxing on the comfy furniture! The host's communication was excellent, warning us of road construction and checking to ensure we arrived without confusion with landmarks. The binder with information was extremely helpful. The hosts even left the lights on for our late evening arrival, and the house was nice and cool from the air conditioning. My kiddos were sad to leave, and we are already planning another trip back!

The Barnbrook House
The barnbrook house was lovely, private and rustic. It had everything our family needed as a base to explore VT/NH. The mountain views are sublime and the house is tucked away offering a lot of privacy. As far as amenities, we loved the toy chest, darts board, and den. There’s plenty of space for a family and Dana stocked up the kitchen with coffee and tea. If you need to be in Hanover for events, this location is a 45 minute drive so keep that in mind when planning.

Modern Farmhouse on 25 Acres - Superb Views
We had a quiet stay at the Farmhouse. Very peaceful and quiet location. Lots of space for our dog to roam. The house is very nice and clean. We enjoyed having coffee and looking out across the fields, reading, and cooking. It’s near the small village of Rochester with a few restaurants and otherwise we explored neighboring towns like Middlebury, Waitsfield, Stowe, and Montpelier.

Beautiful Woodstock Home-Perfect for entertaining
We had a fantastic stay at this beautiful home. We came with our 6 month old and 3 year old daughters and pup. There was plenty of space for the whole family and very kid friendly. We were saying when we were there that it would have been amazing with a group of friends for a girls weekend too! Beautiful spot where you feel like you’re deep in the Vermont woods but super close to downtown Woodstock. Would love to stay again if available!

One Room School House. No Cleaning Fees!
We had an amazing stay! The place is in a fantastic location—perfect for exploring Woodstock or Killington—and it was super cozy, clean, and well-equipped. Robyn and Trevor were outstanding hosts, always quick to respond and incredibly helpful. The easy communication made the entire experience seamless and stress-free. Highly recommended!
Apartment rentals with outdoor seating

Green Street Hideaway. Downtown Lebanon.
Lovely place. Nice and quiet with lots of natural light. The bed and couch were super comfy and the sheets were so soft! Check-in and out were easy, the place was clean and pleasant and I will definitely stay again if I’m ever back in the area. If you take a baking class at King Arthur Flour like I did, this is a great place to stay - less than 15 min away.

Dog heavenly! Private, beautiful and relaxing.
Our second stay here was great, river was a little higher but we wanted a peaceful weekend with friends and dogs. Apartment was warm given the unseasonable cold weather and we had all the amenities we needed even dog towels for wet pups. Did not see the host during our stay but she was in contact as needed.

Overlook at the Office
Small but has a fully equipped kitchen, other than the only sink is in the bathroom. The sink is big and it worked fine. The park is 1/2 block away and town is 2 blocks. Comfortable bed and quiet at night. Good restaurants and unique shops in town. Lots of nature trails close by. Be mindful of having the key it could be easy to get locked out. We enjoyed our time in the apartment and definitely would recommend it to anyone who wants to visit Bristol. Thanks for sharing your place with us.

Cozy Poultney Village Apartment
For the price, this is the perfect spot for a little weekend getaway. The restaurants and surrounding areas are inexpensive and good quality. I would recommend this spot to anyone looking to get away from the city and into nature!

Hideaway Lodge at Lake Dunmore
Loved staying with Sandra and Jason! They are great hosts and did a great job on the Airbnb. We knew there were going to be mosquitoes, but we didn’t know that there were going to be so many, I would advise bringing bug spray. They let us use their kayaks which was an awesome experience. 10/10 would stay again.

Vermont Country Suite
Cindy and Doug were phenomenal hosts and their suite was so lovely to spend the weekend in while skiing at Killington. Their suite was very clean and cozy, and they went above and beyond to make our experience a great one. They provided homemade banana bread, fresh fruit, snacks, coffee, and even left us a bottle of champagne to celebrate our anniversary. This was one of our favorite airbnbs we’ve ever stayed at, and we hope to stay here again on future trips!

Skyeship Woods - 7 Beds + Hot Tub
Amazing and great hosts! Very clean. Perfect for our ski team. we loved enough bed and beautiful views. We will definitely be back. ♡♡♡♡♡♡♡

Suite in the Green Mountains
This was our second, month+ long, stay at Dick & Dorothy's place. It was perfect for the two of us. The internet was reliable with fast speeds which worked great for remote work with zero issues for video calls. They are great hosts and respond quickly to any questions. They apartment is only about 100 yards off of VT 100 and has easy parking which was plowed quickly after any snowfall. There are plenty of options for ski/snowboarding/XC in every direction! Thank you!
Condo rentals with outdoor seating

105 Fox Hollow Village Pvt - Red Fox - Unit B-4
Great place, great host, zero complaints.

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!

Dog-Friendly Mtn Escape/AC/Pool/
Great place! We enjoyed our stay so much that we extended it an extra day. Hosts made it super easy to extend.

Location + Spa! - Cozy 2BR Condo - Mountain Side
We had an amazing stay at this place! The location was perfect—just a short walk to all the incredible relaxation amenities like the pool, steam room, and sauna, which made our trip feel like a true escape. Going for a walk while taking in the views of the mountains were absolutely stunning and made every morning feel special. The unit itself was spotless and had everything we needed for a comfortable, short stay. The kitchen was well-stocked, the bed was cozy, and everything felt thoughtfully arranged. It was the perfect home base for exploring Killington and unwinding after a day of adventure. Would absolutely recommend and may come back during the Peak of the Snow Sport Season!

Walk/Bike to Snowshed Lift 2BR @ Mt. Green Resort!
My family and I had an awesome stay in Tina's apartment. We took full advantage of the outdoor pool and the indoor spa space, which were both fantastic. The unit was a clean, cozy and comfortable place to return to at the end of busy days. Tina was an exceptional host - one of the most responsive/helpful experiences I've had with an Airbnb host. We would definitely stay here again!

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.

Modest Mountain Dacha
Philip was very informative and responsive when we needed. His information was clear and easy to follow. At the end of our stay, when we went to dispose of our trash, we saw a bear at the dumpster bins and he was completely understanding that we couldn’t dispose of it at that time. He had a great sense of humor and made the experience all around great!

Cozy Condo *AC & Pool *
We loved staying at this cozy condo. We were able to find it easily and get inside without any issues. The bed was the best we’ve encountered in an Airbnb! I loved the small creek behind the condo and sitting on the balcony with my tea listening to it was a wonderful way to start the day. We would definitely come back again.
Quick stats about vacation rentals with outdoor seating in Stockbridge
Total rentals
30 properties
Nightly prices starting at
ﺩ.ﺇ257 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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- Stratton Mountain
- Sugarbush Resort
- Okemo Mountain Resort
- Bolton Valley Resort
- Pico Mountain Ski Resort
- Dartmouth Skiway
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Cochran's Ski Area
- Fort Ticonderoga
- Hildene, The Lincoln Family Home
- Dorset Field Club
- Tenney Mountain Resort
- Fox Run Golf Club
- Baker Hill Golf Club
- Country Club of Vermont
- Northeast Slopes Ski Tow
- Bromley Mountain Ski Resort
- Ekwanok Country Club
- Lucky Bugger Vineyard & Winery
- Vermont National Country Club
- Adirondack Extreme Adventure Course
- Mount Sunapee Resort
- Montshire Museum of Science