Vacation rentals with a patio in Pittsfield

Find and book unique patio rentals on Airbnb

Quick stats about vacation rentals with a patio in Pittsfield

  • Total vacation rentals

    Explore 60 vacation rentals in Pittsfield

  • Nightly prices starting at

    Pittsfield vacation rentals start at ﺩ.ﺇ 441 per night before taxes and fees

  • Verified guest reviews

    Over 2,620 verified reviews to help you choose

  • Family-friendly vacation rentals

    60 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    60 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!

Top-rated patio rentals in Pittsfield

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

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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, 258 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

Guest favorite
Home in Bridgewater
4.97 out of 5 average rating, 104 reviews

Breathtaking Riverfront Retreat w/Mountain Views

Thoughtfully designed to elevate every moment of your Vermont getaway, our home offers a comfortable & uniquely historic experience, along with panoramic views of the beautiful Ottauquechee River. Perfectly nestled between the vibrant towns of Woodstock and Killington, guests have incredible hiking, skiing, golfing, shopping, leaf peeping, delicious dining, and so much more right at your finger tips. Wonderful for families, couples, or small groups looking to explore all that VT has to offer!

Top guest favorite
An exterior view of the home showcases a patio adorned with string lights, providing a warm glow against the backdrop of rolling green hills. The hot tub is visible nearby, adding to the inviting outdoor space perfect for gatherings.
Cabin in Killington
4.98 out of 5 average rating, 123 reviews

Camp Poe: HotTub/AC/Game Room/6acres/Patio/EVchrgr

Experience the heart of the Green Mountains on our private 6 acre estate. Camp Poe at Estabrook is the ultimate Vermont getaway--wide plank floors, fully stocked 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, 10ft dining tables (inside AND outside) and hot tub. 13 min to Killington Mtn & 4min to the #1 golf course in VT! EV Charger available for guest use.

Top guest favorite
A wooden cabin is set against a backdrop of colorful autumn foliage. The exterior features multiple large windows and a spacious deck with seating arrangements, including two lounge chairs. A grill and stacked firewood are visible on the deck, inviting outdoor gatherings.
Cabin in Roxbury
4.97 out of 5 average rating, 302 reviews

Off Grid Secluded Farm Stay Cabin

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.

Top guest favorite
A red cabin is nestled within a lush green forest, surrounded by trees. A gravel driveway leads up to the entrance, while a vibrant lawn extends in the foreground. The bright blue sky and soft clouds create a serene backdrop.
Home in Norwich
4.99 out of 5 average rating, 125 reviews

Relaxing Countryside Oasis!

Welcome to our cozy 2BR/1BA cabin, ideal for 6 guests. Relax by the indoor fireplace or outside by the fire pit and hot tub. Listen to the stream from the patio. Fully equipped kitchen and washer/dryer for convenience. Only 10 mins from Dartmouth College and 5 mins to downtown Norwich, VT. Multiple ski resorts within 30-minutes. Perfect for a serene getaway, this cabin offers a blend of comfort, nature, and convenience, ensuring a memorable stay for family, friends, or a romantic retreat!

Guest favorite
Condo in Killington
4.9 out of 5 average rating, 125 reviews

Across from Killington, Arcade, Pool & Hot Tub, AC

The one guests keep coming back to. This oversized 1BR at Mountain Green features an in-unit arcade game, xbox, electric fireplace, year-round indoor pool and hot tub, plus an outdoor pool open Memorial Day through fall. A portable AC keeps you cool in the summer. Located across from one of the country’s top mountain bike parks and minutes from hiking, golf, restaurants, and Killington adventures. Fresh mountain air, resort amenities, and a true Vermont escape without the winter crowds.

Top guest favorite
Tiny home in Ludlow
4.96 out of 5 average rating, 106 reviews

Alpine Reflection + Hot Tub

Escape to this luxury glass tiny home perched at 1,500 feet in elevation in Ludlow, Vermont—architect-designed and built in Estonia with stunning views of Okemo Mountain. Tucked away in a private forest setting, this one-of-a-kind retreat features a hot tub, fire pit, outdoor shower under the trees, radiant heated floors, and floor-to-ceiling windows that immerse you in nature. Designed for quiet luxury relaxation and unforgettable mornings, it’s the perfect escape every season

Guest favorite
An A-frame cabin is nestled among trees with autumn leaves in vibrant shades. A large deck extends from the cabin, featuring a hot tub and outdoor dining area. A barrel sauna is positioned nearby, completing the inviting outdoor space.
Cabin in Mount Holly
4.88 out of 5 average rating, 168 reviews

Okemo A-Frame - Floor Hammock, Sauna & Hot Tub

Welcome to the Okemo A-Frame! With an oversized deck, featuring outdoor dining, a barrel sauna, and hot tub you'll enjoy the outdoors year round. Enter into an open-concept dining area, kitchen, and living room with stylish mid-century malm fireplace. Take your rest in one of the three bedrooms or cozy up on the indoor floor hammock. Located 10 minutes from Okemo Mountain Resort and the town of Ludlow enjoy skiing, shopping, dining, and all that Vermont has to offer.

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, 326 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 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, 163 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.

Top guest favorite
A spacious living area features a large leather sectional sofa facing a glass coffee table. Natural light floods in through multiple large windows, framed by dark trim. A cozy reading nook is seen in the corner, adorned with a decorative throw and a small side table.
Home in Pittsfield
4.98 out of 5 average rating, 42 reviews

Skyeburst | Modern Mtn Home

| Welcome to The Skyeburst House | Reimagined 1970's Mountain Home 15 mins from the Killington K1 Gondola. This is a newly renovated modern home boasting lots of natural light, spa like bathrooms, open floor plan, and exposed cathedral ceilings. Curated with a mix of rustic and modern decor. High quality king and queen beds. Modern appliances. Samsung 75" QLED 4K TV. Sonos Sound System. Fire pit. Deck. Grill. Stars. Your Vermont adventure awaits.

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
4.94 out of 5 average rating, 147 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

Popular amenities for Pittsfield patio rentals

When is the best time to visit Pittsfield?

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Avg. priceﺩ.ﺇ 1,792ﺩ.ﺇ 1,990ﺩ.ﺇ 1,374ﺩ.ﺇ 1,340ﺩ.ﺇ 1,377ﺩ.ﺇ 1,340ﺩ.ﺇ 1,161ﺩ.ﺇ 1,113ﺩ.ﺇ 1,131ﺩ.ﺇ 1,285ﺩ.ﺇ 1,362ﺩ.ﺇ 1,616
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