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Vacation rentals with a patio in Pittsfield

Find and book unique patio rentals on Airbnb

Top-rated patio rentals in Pittsfield

Guests agree: these patio rentals are highly rated for location, cleanliness, and more.

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Top guest favorite
The inviting living room features a modern wood-burning stove against a backdrop of light wooden walls. A comfortable dark sofa is arranged around a round wooden coffee table, complemented by a decorative plant. Natural light filters through the windows, enhancing the cozy atmosphere.
Cabin in Londonderry
4.95 out of 5 average rating, 222 reviews

Summit View Cottage:Ski | Hot tub|Fireplace3bd 2ba

Summit view cottage boasts 3 acres in the beautiful green mountains, we are 1,700 feet up in elevation . At this brand newly built PET FRIENDLY cabin you will have 3 bedrooms and 2 full bathrooms, which will sleep 7 comfortably. We have a brand new 6 person HOT TUB! You will find yourself within 15 minutes to the world famous Stratton mtn, 15 minutes from Bromley mtn and a close 4 minutes to the local Magic mtn.Very close proximity to the town of Manchester, which has great shops and restaurants

Top guest favorite
An aerial view showcases a large, red two-story building with a metal roof nestled among lush greenery. The property features multiple decks and a private outdoor space. The surrounding landscape provides a serene backdrop of trees and grass, enhancing the natural setting.
Guest suite in Lake Bomoseen
4.97 out of 5 average rating, 236 reviews

My house is your house!

Relax in this refurbished quiet Lake view rental. Minutes from Lake Bomoseen/Crystal Beach. Large family room, Cast iron wood-stove. Wall of windows w/lake views. 65" 4K w/ surround sound. w/ game hook-up. Wi-Fi. Galley kitchen includes range, microwave, Keurig, fridge & wine cooler. Spacious bedroom, queen size bed w/ heated mattress pad. Lots of storage.Full bathroom. Private deck w/Adirondack chairs. Kayaks & boat launch. 15 miles to Rutland, 35 min to Pico & 47 min Killington Ski Resorts.

Top guest favorite
A bright and airy living space features a cozy wood-burning stove and large windows that invite natural light. Rustic wooden beams complement the warm plank flooring. A comfortable seating area is arranged near the windows, enhancing the inviting atmosphere.
Cabin in Killington
4.97 out of 5 average rating, 112 reviews

Camp Poe: Hot Tub+Game Room+Bar+6acres+Patio+AC

Experience the heart of the Green Mountains on our private 6 acre estate. Camp Poe at Estabrook is newly renovated while still maintaining its original Vermont charm--wide plank floors, farmhouse kitchen, wooden beams and a two story family room w/ a wood burning stove. This 3200 sq ft house is perfect for entertaining with two separate living rooms, bar, game room, 12 foot dining tables (inside AND outside) and hot tub. 13 min to Killington Mtn, 10 to Pico & 4min to the #1 golf course in VT!

Top guest favorite
Home in Killington
4.93 out of 5 average rating, 138 reviews

Gorgeous Dog Friendly 2BR 2.5 Bath w/ Pool Sauna

Our 2-bedroom, 2.5-bath Airbnb, nestled in Vermont’s Green Mountains, invites you to escape into a haven of year-round adventure. Enjoy breathtaking views of a scenic pond, skiing through pristine slopes, bike along winding trails, or hike amidst the number 1 ranked foliage in the USA. Rejuvenate in the indoor pool and spa, with hot tubs, steam rooms, sauna and gym. Unwind by the cozy fireplace, creating unforgettable memories. Experience the charm and beauty of Killington like never before.

Guest favorite
A secluded cabin is nestled among snow-covered trees, showcasing a timber exterior and large windows that reflect the winter landscape. An inviting deck extends from the cabin, surrounded by a tranquil blanket of snow, creating a serene atmosphere.
Cabin in Roxbury
4.97 out of 5 average rating, 271 reviews

Off Grid Secluded Cabin on 37 Acre Farm

In a secluded, hand-crafted off the grid cabin, come and enjoy the elements with us at Drift Farmstead. A 3-minute walk leads you through gardens and pasture, to Ravenwood, a small, intimate cabin with everything you need. Be it an extended weekend tucked in seclusion, amongst the birds, river and trees, or find the comforts of a 37 acre small farm nestled in the mountains and settle in, working from afar. Top shelf skiing at Sugarbush is near, along with Vermont's finest grub and beer.

Guest favorite
Condo in Killington
4.94 out of 5 average rating, 126 reviews

Shuttle/Across from Mtn/Pool/Gym/Hot Tub/Xbox

Experience comfort and convenience in this renovated 1BR/1BA condo in Mountain Green building #3. Ideally located across from Snowshed and Ramshead lodges, it offers easy access to year-round activities. The condo features an open floor plan with a spacious living area, a fully updated kitchen, and modern finishes throughout. A free shuttle service stops at the building in winter. With all the amenities you need, this stylish retreat is the perfect getaway for all seasons!

Top guest favorite
A cozy living area is highlighted by warm wood paneling and large windows allowing natural light. A stylish record player is placed on a small table near a comfortable seating arrangement featuring a light sofa and wicker chairs. A decorative rug and a small stove add to the inviting ambiance.
Cabin in Roxbury
4.98 out of 5 average rating, 192 reviews

Cozy cabin retreat

This is the cozy, romantic cottage you've been dreaming of! Fall asleep to the sound of the stream outside the window. Enjoy sledding, snowshoeing, or XC skiing around the meadow, or use this as a convenient base for all your Vermont adventures. Nestled in a hidden valley in the center of Vermont, the cottage is conveniently located a short drive from many ski areas, award-winning Montpelier and Randolph restaurants, the bustle of the Mad River Valley and I-89.

Top guest favorite
A modern house with wooden exterior is shown from an elevated perspective, surrounded by autumn foliage. A hot tub is positioned on a spacious deck, which includes a seating area with four chairs and a small table. Scenic mountain views and vibrant trees enhance the natural setting.
Tiny home in Warren
4.99 out of 5 average rating, 275 reviews

Luxury Glass Tiny House - Mountain View + Hot Tub

Immerse yourself in nature at Vermont's most unique Airbnb, located in the heart of the Green Mountains. This upscale mirrored glass house was built in Estonia and combines Scandinavian design with jaw-dropping Vermont views for an unforgettable experience. You'll return home feeling rejuvenated after relaxing in a hot tub overlooking Sugarbush Mountain or waking up with a panorama of Blueberry Lake at your feet. *One of Airbnb’s Most Wish-listed Stays of 2023*

Top guest favorite
A comfortable living area features a wood fireplace with tools nearby and a mounted television above it. Two armchairs flank a rustic coffee table, creating a cozy space. Large windows allow natural light to fill the room while offering views of the snowy outdoors.
Home in Killington
4.91 out of 5 average rating, 102 reviews

Ski home to Trail Creek!

Enjoy Killington at competitive pricing without sacrificing comfort! Located in Trail Creek Condo Association. • Ski, hike, bike, or golf just steps away • Cozy up by the wood fireplace (free wood) • Pool, hot tubs, sauna, and game room at community center • 6-minute walk to Snowshed or shuttle (winter weekends/holidays) • Ski home trail (snow-dependent) • Minutes to restaurants, bars, and shops • Convenient bus stop Adventure and relaxation await!

Top guest favorite
A stone pathway is framed by lush greenery and garden beds leading to the entrance of the chalet. Soft lighting from lanterns illuminates the steps, creating a welcoming atmosphere as it transitions from the natural surroundings to the home's entrance.
Chalet in Stockbridge
4.97 out of 5 average rating, 146 reviews

Gnome Home Mountain Ski Chalet w/Sauna Killington

Mountaintop Chalet perched in the heart of Green Mountains. Enjoy true mountain living all year long 25m to Killington, White River access minutes from home, abundance of hiking trails, and golf courses. Central to Killington, Rochester, & Woodstock. After your adventures, return to a welcoming & comfortable home with beautiful views from every room, multiple decks, new! fireplace, & sauna, and plenty of special touches to help you unwind and relax.

Guest favorite
A private deck with a hot tub is surrounded by colorful planters filled with seasonal flowers and pumpkins. The entrance to the cabin features a welcoming door framed by autumn decorations, backed by lush greenery from the surrounding forest.
Cabin in Chittenden
4.95 out of 5 average rating, 129 reviews

Outside Inn - Hot Tub/Killington/MtnTop Inn/VAST

Reconnect with nature at the Outside Inn, a four season retreat, locally known as the Labor of Love. A man fell in love with a woman, but when he asked for her fathers blessing he said, first you must build her a home. So he built this beautiful post and beam cabin and they lived happily ever after! *Decorated seasonally!* IG/TikTok: outside_inn_vt FB: Outside Inn VT

Top guest favorite
A cozy bedroom features a spacious king bed dressed in a plaid blanket, complemented by decorative pillows. Two bedside lamps provide soft illumination. A wood shelf above the bed holds decorative items. A large window offers a view of the outdoors, dressed with light curtains.
Home in Killington
4.98 out of 5 average rating, 146 reviews

CozyDen-Location, Fireplace, Ski Off/Shuttle On!

Welcome to our cozy 1-bedroom condo in Killington, VT! Ski off and shuttle on, close to everything including biking and golfing. Enjoy the wood-burning stove, comfortable furnishings, and well-equipped kitchen. Rest well in the king bed and explore the slopes, trails, and golf courses nearby. Relax on the porch or by the fire. Your perfect Killington getaway awaits!

Popular amenities for Pittsfield patio rentals

When is the best time to visit Pittsfield?

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Quick stats about vacation rentals with a patio in Pittsfield

  • Total vacation rentals

    Explore 50 vacation rentals in Pittsfield

  • Nightly prices starting at

    Pittsfield vacation rentals start at $140 per night before taxes and fees

  • Verified guest reviews

    Over 2,320 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Pittsfield vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Pittsfield rentals

  • 4.9 Average rating

    Pittsfield stays are highly rated by guests—averaging 4.9 out of 5!

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