Holiday rentals with a patio in Pittsfield

Find and book unique rentals with patio on Airbnb

Top-rated rentals with patio in Pittsfield

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

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Guest favourite

Barn in Ripton

4.93 out of 5 average rating, 146 reviews

Green Mountains Vermont Middlebury Bread Loaf Barn

Come stay at our lovely renovated barn guesthouse in the Green Mountains of Vermont near Middlebury College. Perfect spot for a quiet retreat or home base for your outdoor adventure! 3 min. to Rikert Nordic Center, 9 min. to Middlebury SnowBowl. 40 min. to Sugarbush. 1 hr to Killington. Sleeps 1-6 people on 3 floors: entry level living area and laundry; mid-level with kitchen, bedroom, and bathroom ; upstairs loft bedroom suite with seating area (futon, chairs, bookcase, and TV), and desk.

22 Feb – 1 Mar

€ 168 per night

Guest favourite

Apartment in Killington

4.95 out of 5 average rating, 130 reviews

🎿Cozy Fireplace Condo-Mins. to Everything 🚵

Seeking Adventure? This end unit garden level condo is 6 minutes to Killington AND Pico! Quick access to the Appalachian Trail to ATV, mountain bike, hike, and swim. Relaxing? Work remotely with fast Wi-Fi, hang on the porch swing, or unwind in front of the wood fireplace. Hop in the power adjustable king bed, pull the darkening shades, and turn on the sound machine for restful sleep so you can wake up and do it again! A portion of each stay is donated to local VT nonprofits

2–9 May

€ 111 per night

Guest favourite

Guest suite in Castleton

4.98 out of 5 average rating, 120 reviews

Mi Casa es su Casa!

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 TV, surround sound system. Wi-Fi access. 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. 25 min to Rutland, 35 min to Pico & 47 min Killington Ski Resorts.

20–27 Oct

€ 121 per night

Guest favourite

Cabin in Roxbury

4.97 out of 5 average rating, 188 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.

9–16 Feb

€ 145 per night

Guest favourite

Cabin in Roxbury

4.98 out of 5 average rating, 120 reviews

Cozy cabin retreat

Find peace, quiet, privacy, and fast high-speed internet at this cabin in Vermont's central hills. The cozy, wood cabin overlooks a small stream and beautiful, rolling meadows. Explore the 26 acres on private forest trails, meadow paths, and surrounding dirt roads. We are close to Montpelier, Northfield, Norwich University, the Mad River Valley, and Randolph. Come for foliage, skiing, mountain biking, or relaxing. (45 minutes to Sugarbush base lodge, 1 hour to Stowe and Killington.)

8–15 Apr

€ 152 per night

Guest favourite

Apartment in Killington

4.96 out of 5 average rating, 103 reviews

CozyCub Pets, AC, Bike to Mtn, Fireplace, Walk out

Delight in this friendly, fully renovated (2022) modern ski condo next to Killington's popular Snowshed base area, learn-to-ski trails, and golf course. Shuttle-On / Ski-Off to the condo during peak season. The location is prime for accessing everything the area has to offer. Relax for some streaming after a day on the mountain on the 65" TV. Enjoy the Whiffletree condo association's outdoor pool and tennis courts in the summer, settle in by the gas fireplace, or head out to explore.

29 Nov – 6 Dec

€ 364 per night

Guest favourite

Cabin in Bristol

4.95 out of 5 average rating, 108 reviews

Cozy Cabin on the River in Bristol

Come experience true tranquility in this vintage and cute riverside cabin. The calming babble of the rocky New Haven River is the perfect soundtrack for you to relax, play, and explore. The small cabin has a deck and plenty of outdoor space with a picnic bench and fire pit. Feels remote but just a two minute drive to charming downtown Bristol featuring great restaurants, bars and shopping. Outdoorsy people will love all the swimming and hiking in the area as well!

22–29 Apr

€ 195 per night

Guest favourite

Flat in Middlebury

4.99 out of 5 average rating, 103 reviews

Mountain View Retreat

This clean, quiet, ground-level apartment enjoys an out-of-town feel and expansive mountain views while being conveniently located to the town of Middlebury, Middlebury College, the Green Mountain National Forest, the Middlebury College Snow Bowl and the Rikert Nordic Center, and more. This 1 bedroom/1 bath apartment features an open living concept and a fully equipped kitchen and is just 1.5 miles from restaurants and grocery stores and 2 miles from the college.

19–26 Jul

€ 203 per night

Guest favourite

Chalet in Stockbridge

4.95 out of 5 average rating, 85 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.

6–13 Sep

€ 434 per night

Guest favourite

Apartment in Killington

4.87 out of 5 average rating, 149 reviews

⛷☃️Close to lifts. Rustic. Mountain Green Resort🏂❄️…

This rustic Mountain Green Resort condo offers easy access to ski/mtn bike lifts with resort style amenities. Features include 4K Smart TVs, High speed WiFi, private balcony with mountain views, board games, and full kitchen. On-site health spa including pool, sauna, hot tub, gym, masseuse. Restaurants and nightlife are minutes down the road. Restaurant/bar and ski/rental shop also within resort. Free shuttle to lifts available during ski season.

23–30 May

€ 155 per night

Guest favourite

Tiny home in Warren

4.99 out of 5 average rating, 154 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.

4–11 Sep

€ 605 per night

Guest favourite

Flat in Goshen

4.86 out of 5 average rating, 14 reviews

Rocky Meadow Farm

Bordering Green Mountain National Forest and minutes from Long Trail this unique spot offers a peaceful getaway. Stunning views, hiking trails, skiing, snow shoeing, cross country skiing, mountain biking, kayaking, fishing and much more can be enjoyed during your stay at this dripping with character location. Sun Bowl in Middlebury only 20 min away, Killington 45 minutes, and Sugarbush about 55 minutes.

13–20 Dec

€ 138 per night