Vacation rentals with a patio in Pittsfield

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Top-rated patio rentals in Pittsfield

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Guest favorite

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.

Feb 22 – Mar 1

G$33,257 GYD per night

Guest favorite

Condo in Killington

4.95 out of 5 average rating, 131 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

Aug 10 – 17

G$20,796 GYD per night

Guest favorite

Guest suite in Castleton

4.98 out of 5 average rating, 122 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.

Dec 16 – 23

G$25,081 GYD per night

Guest favorite

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.

Feb 14 – 21

G$27,807 GYD per night

Guest favorite

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.)

Sep 23 – 30

G$30,820 GYD per night

Guest favorite

Condo 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.

Mar 7 – 14

G$87,895 GYD per night

Guest favorite

Cabin in Bristol

4.95 out of 5 average rating, 109 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!

Mar 27 – Apr 3

G$36,461 GYD per night

Guest favorite

Apartment 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.

Jun 14 – 21

G$39,021 GYD per night

Guest favorite

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.

May 17 – 24

G$54,291 GYD per night

Guest favorite

Condo 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.

Jun 9 – 16

G$35,032 GYD per night

Guest favorite

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.

Oct 16 – 23

G$155,662 GYD per night

Superhost

Cabin in Stockbridge

4.89 out of 5 average rating, 18 reviews

1920s "Golden Age" Cabin w/ Breathtaking Views!

Welcome to CAMP TREETOPS, located in the heart of the beautiful Vermont mountains. Our cabin is nestled at the top of a private mountain, surrounded by breathtaking views of Killington, Pico mountains, and the White River. Step back to the golden age of travel and enjoy a unique vacation rental experience. The cabin honors the 1920s era with carefully curated antique furniture and vintage décor.

Dec 27 – Jan 3

G$53,786 GYD per night