Vacation rentals with outdoor seating in Stockbridge

Find and book unique outdoor seating rentals on Airbnb

Top-rated outdoor seating rentals in Stockbridge

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Superhost

The exterior of the Granary is highlighted, featuring a mix of red barn siding and natural stone. The two upper windows allow natural light inside, while a mint green double door adds a pop of color. Lush greenery and colorful flowers surround the entrance.

Guesthouse in Lenox

4.92 out of 5 average rating, 394 reviews

Restored 1735 Granary I King Bed + Views & Pool

Restored 1735 granary on a peaceful Berkshires farmhouse compound. With 15-ft vaulted ceilings, original wide-plank floors, and mountain views, this design-forward retreat blends rustic charm with modern ease. Features a king bedroom, eat-in kitchen, and bathroom with soaking tub + standing shower. Centrally located in the Berkshires and just minutes to Lenox and Tanglewood. A quiet, light-filled space perfect for couples, creatives, and anyone seeking rest, reflection, and connection to nature.

Guest favorite

A charming architectural structure is nestled among lush greenery, framed by a variety of trees. A rustic wooden bench sits in the foreground, inviting guests to relax and enjoy the serene natural surroundings. Soft light emanates from the windows, enhancing the inviting atmosphere.

Chalet in Otis

4.95 out of 5 average rating, 431 reviews

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Superhost

An open living space showcases wooden beams and natural light. A cozy seating area features a plush couch, patterned cushions, and a round coffee table. A dining area is visible, complemented by a well-equipped kitchen in the background. A ship ladder leads to a sleeping loft above.

Cabin in Stockbridge

4.88 out of 5 average rating, 222 reviews

Hip Stockbridge Cabin - A stroll to the lake

Hello hip, glamping cabin! The decor is chic & bohemian cool! Enjoy the large yard & sunny deck. Fieldstone fireplace w/ vaulted ceilings & skylights. Cottage has beautiful pine throughout w/ fabulous interior design picks. Enjoy the sweet reading nook, master bedroom w/ skylights or put on a favorite record. Kids will love the sleeping loft. A 9 minute walk or 2 minute drive to lake public beach (The lovely Stockbridge Bowl) . BBQ grill, outdoor fire pit . Gates of Tanglewood minutes aaway!

Guest favorite

A charming cottage is framed by vibrant flowering shrubs and greenery. The front porch is adorned with decorative elements, while large windows invite natural light into the space. A wooden fence encloses the front garden, enhancing the quaint and inviting atmosphere.

Cottage in Great Barrington

4.93 out of 5 average rating, 305 reviews

Artist Cottage

Enchanting, private, romantic, retro style, artsy, cottage & lodge building with fireplaces and outdoor hot tub and shower area in a quaint, quiet, neighborhood nested at the base of Flag Rock and near nature trails and downtown Great Barrington. Perfect for a romantic get-away. Open retro style kitchen with wood stove and TV is stocked with utensils and pans for cooking with gas oven and retro appliances. Upstairs bedroom with ensuite large bathroom with soaking tub and message chair.

Top guest favorite

A charming two-story home is set on a landscaped plot with a gravel driveway. A wooden staircase leads to the entry, flanked by vibrant flower beds. The natural backdrop features lush trees and a striking granite ledge, creating a peaceful and inviting outdoor environment.

Home in Great Barrington

4.99 out of 5 average rating, 127 reviews

Granite Ledge, Modern home in a unique setting

Welcome to Great Barrington, the heartbeat of the Berkshires! This newly remodeled home that sits on 3.5 acres, is conveniently located 1 min from Butternutt Ski Mountain, and a 6 min drive from downtown main street Great Barrington. Convenient to restaurants, shops, farmers markets, art galleries, Tanglewood, Stockbridge, The Norman Rockwell Museum, Simon’s Rock, etc. Enjoy a vibrantly diverse restaurant scene and cultural events while still staying in a private setting.

Guest favorite

Home in Lee

4.99 out of 5 average rating, 287 reviews

Berkshire Mountain retreat with Urban eco-luxuries

600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, hear the great musicians at Tanglewood, take in a play at Shakespeare & Co, or just relax by the firepit- we hope you enjoy your stay and will visit us again.

Top guest favorite

A two-story home is depicted, featuring a grey wooden exterior with multiple windows. A wooden deck with stairs leads to the entrance, surrounded by green grass and vibrant yellow flowers. The clear blue sky complements the inviting structure.

Farm stay in Pittsfield

4.99 out of 5 average rating, 249 reviews

Private 2nd-floor studio on a working produce farm

Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or just relax out on the balcony and take in the views.

Top guest favorite

An entryway features a grey console table with glass-front cabinets, topped by a table lamp and a potted plant. A round mirror hangs above the table, while a doorway leads into the home, revealing glimpses of the kitchen and hallway beyond.

Home in Stockbridge

4.95 out of 5 average rating, 141 reviews

Sun-filled, Charming Stockbridge Classic- In Town!

Beautiful remodel on a classic old, well-appointed New England house located in the middle of town on a dead-end road leading to hiking trails for Laura's Tower. A quick walk to Downtown Stockbridge, Red Lion Inn, gas station, cafes, markets, shops... everything you need. A park sits directly across the street with open acreage, swings, sandbox, skate park. Parking available on site. Located within minutes of four season activities- happy to make recommendations!

Superhost

A modern, renovated barn is set against a backdrop of lush greenery. Two brightly colored lounge chairs and a reclining chair are positioned on the grassy area, inviting relaxation. Large windows reflect the surrounding trees, emphasizing the tranquil outdoor setting.

Guesthouse in Stockbridge

4.89 out of 5 average rating, 140 reviews

Modern barn in the heart of the Berkshires

Modern, renovated, historic dairy barn in the heart of the Berkshires. Located on 3.5 acres with beautiful views and close to everything. 1.5 miles to Main St Stockbridge/Red Lion Inn, 5 minutes to Tanglewood, 5 minutes to the Stockbridge Bowl and beautiful hiking trails, under 10 minutes to Lenox . This is the perfect base for exploring the Berkshires or a great getaway for relaxing and enjoying nature.

Top guest favorite

A charming cottage is illuminated from within, showcasing a welcoming porch with steps leading down to a spacious grassy yard. The exterior features light blue siding and a deck equipped with a grill, set against a backdrop of trees and a fenced yard.

Home in Stockbridge

4.89 out of 5 average rating, 103 reviews

Rabbit Run in the heart of Stockbridge Village

Old meets new in this lovely cottage, a short walk from the Red Lion Inn. Lots of light, comfortable, traditional furniture, beautiful, fenced-in backyard with mountain views. Kitchen updated with Smeg refrigerator, gas stove, granite counters, hardwood floors throughout. Hiking trails, park, and tennis courts within a 5-minute walk. Lake rights to Stockbridge Bowl, Weber grill, and Solo firepit.

Guest favorite

A serene bedroom features a spacious bed dressed in soft linens and a colorful quilt. A cozy couch is positioned against the wall, offering a relaxation spot. Natural light is let in through multiple windows, highlighting the light blue paneled walls and white furniture.

Home in Lee

4.97 out of 5 average rating, 109 reviews

Stylish Mid-century Modern Berkshires Cape

Stylish and design forward, yet entirely comfortable for families and kids. Fully renovated 4 bedroom, 2.5 bath home located in the heart of the Berkshires. Enjoy the large, sunny yard and deck with lots of seating and a large dining table - perfect for al fresco dinner and drinks! The house is decorated in mid century modern style with gorgeous design touches throughout!

Guest favorite

The charming farmhouse is set back from the gravel drive, surrounded by a lush green lawn and mature trees. The exterior features blue-grey siding and a welcoming porch, with neatly placed potted plants adding a touch of color.

Cottage in West Stockbridge

4.95 out of 5 average rating, 142 reviews

Historic 1810 Farmhouse - Fully Renovated

Charm and history meet modern convenience in this stunning renovated farmhouse. Built in 1810, this beautiful home was once the residence of Mr. Prince, who presided over the Tobey Quarry Farm. Just steps into town, the cottage is the ideal retreat for a low-key, cozy getaway. Or as a launch pad to the area's many outdoor/cultural offerings. We warmly welcome you!