Vacation rentals with outdoor seating in Stockbridge

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Popular amenities for Stockbridge outdoor seating rentals

House rentals with outdoor seating

Guest favorite
Aerial view of a snow-covered landscape, showcasing rolling hills and a winding road. The scene includes a mix of bare trees and patches of evergreen, while the distant mountains hint at recreational opportunities. A clear sky and soft sunlight enhance the serene atmosphere.
Home in Killington
4.91 out of 5 average rating, 213 reviews

Luxury Condo Tucked in the Heart of Killington

JessicaRating, 5 stars3 days ago
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!
Top guest favorite
A spacious deck features several black reclining chairs arranged around a white table. Vivid autumn foliage is visible in the background, along with distant mountains and a clear blue sky. The scene invites relaxation in a serene outdoor setting.
Home in Orford
4.98 out of 5 average rating, 124 reviews

Romantic Mountain Getaway

TaisiyaRating, 5 stars1 week ago
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
Guest favorite
A hammock is set up under the shade of tall trees, surrounded by lush greenery. A gravel pathway leads to the seating area, with a rustic barrel positioned nearby, creating a serene space for relaxation in nature.
Home in Fairlee
4.96 out of 5 average rating, 508 reviews

Cozy Bow House Perched in Trees w/ Hot Tub & View

PhillipRating, 5 stars3 days ago
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.
Guest favorite
A bright yellow wall features a modern artwork piece framed above a set of wooden steps. The wood accent of the steps complements the white wainscoting that runs along the base of the wall.
Home in Bethel
4.94 out of 5 average rating, 101 reviews

Comfortable 3 Bedroom King size Master w/ En suite

RebeccaRating, 5 stars3 days ago
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!
Top guest favorite
Home in Tunbridge
4.97 out of 5 average rating, 393 reviews

The Barnbrook House

AartiRating, 5 stars1 week ago
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.
Guest favorite
A vast green meadow is depicted, dotted with bright yellow wildflowers. In the background, a classic red barn stands amidst rolling hills and gentle mountains, surrounded by clusters of trees and open fields, showcasing the serene landscape of rural Vermont.
Home in Rochester
4.97 out of 5 average rating, 144 reviews

Modern Farmhouse on 25 Acres - Superb Views

BrandonRating, 5 stars2 months ago
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.
Top guest favorite
A newly renovated house is nestled among tall trees, surrounded by lush greenery. The structure features multiple windows reflecting sunlight, with a wooden deck visible in the foreground, leading to a serene setting that invites outdoor relaxation.
Home in Woodstock
5 out of 5 average rating, 133 reviews

Beautiful Woodstock Home-Perfect for entertaining

EmmaRating, 5 stars6 months ago
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!
Top guest favorite
Home in Rutland
5 out of 5 average rating, 138 reviews

One Room School House. No Cleaning Fees!

JesseRating, 5 stars3 months ago
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

Guest favorite
A cozy living room is highlighted by exposed wooden beams and warm, natural light. A soft sofa with decorative pillows faces a simple coffee table, with a chair positioned by a window. A small side table with a lamp adds to the inviting space.
Apartment in Lebanon
4.89 out of 5 average rating, 659 reviews

Green Street Hideaway. Downtown Lebanon.

LauraRating, 5 stars5 days ago
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.
Top guest favorite
An open living space is captured, featuring a comfortable couch, a colorful chair, and a round coffee table. Natural light brightens the room, highlighting a kitchenette area and coordinating furnishings across the suite. High ceilings contribute to an airy atmosphere, creating a welcoming environment.
Apartment in Clarendon
4.95 out of 5 average rating, 310 reviews

Dog heavenly! Private, beautiful and relaxing.

MarindaRating, 5 stars1 month ago
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.
Guest favorite
A vibrant autumn landscape is captured, featuring a variety of trees adorned with bright orange, red, and yellow leaves. A winding river is visible in the foreground, surrounded by the lush greenery of the season. Overcast skies provide a soft light over the scene.
Apartment in Bristol
4.86 out of 5 average rating, 156 reviews

Overlook at the Office

JillRating, 5 stars2 weeks ago
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.
Top guest favorite
A two-story, white wooden house is surrounded by lush greenery and shrubs. A porch with a small seating area is visible, along with an air conditioning unit installed on the upper level's front wall. The bright sky and soft clouds provide a picturesque backdrop.
Apartment in Poultney
4.94 out of 5 average rating, 352 reviews

Cozy Poultney Village Apartment

TeoRating, 5 stars1 week ago
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!
Guest favorite
A serene lake scene is presented at sunset, with a solitary kayaker navigating the calm waters. The reflection of the sun creates a shimmering path across the lake's surface, while trees line the distant shore, adding to the peaceful atmosphere.
Apartment in Leicester
4.95 out of 5 average rating, 101 reviews

Hideaway Lodge at Lake Dunmore

IzakRating, 5 stars2 weeks ago
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.
Top guest favorite
A cozy bedroom features a spacious bed with a white quilt and decorative pillows. Natural light enters through two windows, illuminating the room's soft blue walls. A bedside table with a lamp is positioned next to the bed, adding functional charm to the space.
Apartment in Chittenden
5 out of 5 average rating, 248 reviews

Vermont Country Suite

MichaelRating, 5 stars2 months ago
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!
Guest favorite
A blue house is nestled among vibrant autumn foliage. A directional sign labeled 'Skyeship House' points the way along a gravel path leading towards the front entrance, framed by trees showcasing warm seasonal colors.
Apartment in Bridgewater
4.87 out of 5 average rating, 106 reviews

Skyeship Woods - 7 Beds + Hot Tub

SarahRating, 5 stars1 month ago
Amazing and great hosts! Very clean. Perfect for our ski team. we loved enough bed and beautiful views. We will definitely be back. ♡♡♡♡♡♡♡
Top guest favorite
A charming two-story white building features a black metal roof and multiple windows with shutters. A covered porch extends across the front, decorated with vibrant flower baskets. Surrounding greenery contributes to the rural setting, with the presence of a neighboring structure visible in the background.
Apartment in Hancock
4.96 out of 5 average rating, 160 reviews

Suite in the Green Mountains

PatrickRating, 5 stars2 months ago
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

Guest favorite
The exterior of the building is shown against a backdrop of a green and orange hillside. Surrounding landscaping includes neatly trimmed bushes, with a paved parking area featuring two parked cars. The structure has a mix of stone and brick accents, complemented by gray roofs.
Condo in Mendon
4.88 out of 5 average rating, 112 reviews

105 Fox Hollow Village Pvt - Red Fox - Unit B-4

MichaelRating, 5 stars1 month ago
Great place, great host, zero complaints.
Superhost
A modern living area is presented with a cozy sofa and decorative throw pillows. A sleek wall-mounted TV rests above a rustic fireplace, with a stylish media console below. Light wood accents and a geometric patterned rug contribute to the inviting decor centered around comfort and relaxation.
Condo in Killington
4.94 out of 5 average rating, 171 reviews

Renovated unit, prime location! Shuttle on/Ski off

KristenRating, 5 stars3 months ago
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!
Guest favorite
A cozy living room features a dark leather sofa adorned with decorative pillows. Above the couch, three framed nature-themed art pieces display serene mountain landscapes. A dog rests comfortably on the carpet, with soft lighting from two side lamps enhancing the peaceful ambiance.
Condo in Killington
4.95 out of 5 average rating, 132 reviews

Dog-Friendly Mtn Escape/AC/Pool/

CarlaRating, 5 stars4 weeks ago
Great place! We enjoyed our stay so much that we extended it an extra day. Hosts made it super easy to extend.
Superhost
The living area features a spacious navy sofa adorned with colorful pillows and a light wooden coffee table. A round dining table with black chairs is present, alongside a large mirror and soft lighting that enhance the inviting space. Natural light filters through the sliding doors.
Condo in Killington
4.89 out of 5 average rating, 130 reviews

Location + Spa! - Cozy 2BR Condo - Mountain Side

DillonRating, 5 stars2 months ago
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!
Top guest favorite
The living area features a cozy seating arrangement with a brown couch and recliners, complemented by a decorative area rug. A coffee table sits in front of the seating, and a dining table with wooden chairs is positioned nearby. Soft lighting enhances the welcoming ambiance.
Condo in Killington
4.94 out of 5 average rating, 235 reviews

Walk/Bike to Snowshed Lift 2BR @ Mt. Green Resort!

LiamRating, 5 stars6 days ago
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!
Superhost
A spacious sleeping area features a large bed with a textured gray coverlet, complemented by two decorative pillows. Flanking the bed are wooden nightstands with lamps. A wall art piece consisting of circular shapes adds visual interest, while natural light filters in through the nearby window.
Condo in Ludlow
4.84 out of 5 average rating, 130 reviews

Okemo Clock Tower Base Ski-in/Ski-out Condo

StephenRating, 5 stars2 months ago
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.
Guest favorite
The living area features a soft gray couch and a black lounge chair, complemented by a textured area rug. Natural light enters through a large window dressed with light curtains. A wooden cabinet and an art piece with an animal illustration are also present.
Condo in Warren
4.83 out of 5 average rating, 116 reviews

Modest Mountain Dacha

BethRating, 5 stars1 day ago
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!
Top guest favorite
A living room with a gas fireplace built into a brick facade provides warmth. A comfortable sectional couch faces the fireplace, complemented by a small coffee table. Large sliding glass doors open to a balcony, offering views of greenery outside.
Condo in Killington
4.99 out of 5 average rating, 114 reviews

Cozy Condo *AC & Pool *

StephanieRating, 5 stars1 week ago
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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