
Vacation rentals with a patio in Pittsfield
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Top-rated patio rentals in Pittsfield
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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.

Bluebird Studio- Light filled and airy
This studio apartment attached to the main house has a style all its own. Contemporary design with high ceilings, clerestory windows and a skylight. Spaces include a large Living Room/Bedroom, Kitchen/Dining area, bathroom with a step-in shower and an adjoining Dressing Room with vanity and sink. There is also an outdoor covered space to enjoy. Furniture includes a Queen size bed, 3 comfy chairs, small round table and 4 chairs. Location is a bit more than one mile from downtown Middlebury.

In-Town Norwich 1.5 miles to Hanover/Dartmouth
Located in the center of Norwich, this modern townhome-style accommodation is a wing attached to our residence. Enjoy your upstairs master suite + office/2nd bedroom, downstairs "café" and all-season sunroom. Relax with a view to the garden and woods beyond. We are 1.5 miles to Hanover/Dartmouth, and 1.0 mile to King Arthur Baking. Our street is part of the Appalachian Trail, and you will be near many Upper Valley attractions. We live onsite and are available to assist you upon request.

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.

Birdie's Nest Guesthouse
Welcome to our newly renovated studio apartment, nestled among the trees in the serene hills of West Windsor, Vermont. Elevated on the second floor, this separate structure offers a tranquil escape with breathtaking views of Mount Ascutney and our own private pond. Immerse yourself in the comforts of this thoughtfully designed studio apartment, surrounded by the natural beauty of the Vermont landscape. Every detail has been curated to ensure your utmost comfort and enjoyment.

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.

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*

Ski Back 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!

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.

⛷☃️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.

Baby Queens Barbie-core Studio Apt (dog friendly)
Enjoy a stylish experience at this centrally-located place. This studio apartment is perfect for the solo traveller or couple. The queen bed is super comfy. Brand new and renovated throughout. The kitchen is stocked for basic cooking. I'll make sure there is always coffee and cream for you. Pets are welcome if they do not get up on the furniture. It's easy access to downtown Rutland to enjoy yoga studios, restaurants, and coffee shops.

Dog-Friendly Mtn Escape/Pool/Gym/Hiking Trails
Experience year-round adventure at Sunrise Village at Killington, just steps from scenic trails and the Sunrise Village Triple Lift (488 ft away). After a day of outdoor fun, unwind by the cozy gas fireplace. Explore nearby hiking, mountain biking, kayaking, and golfing. The indoor sports complex—featuring a pool, hot tub, and gym—is a short walk away. Perfect for outdoor lovers looking to relax and make unforgettable memories!
Popular amenities for Pittsfield patio rentals
Apartment rentals with a patio

Rocky Meadow Farm

Vermont Ski / Okemo / Killington / Pico / Stratton / Bromley

Newly renovated condo-The Woods

Green Mountain Collection: Cozy Vermont Haven

Spacious Home Near Heart of Middlebury Fiber Wifi

Mountain View Retreat

Brookside

Hebard Hill Hideaway
House rentals with a patio

Stunning Mountain Views

Charming Modern Cabin Retreat

Lake Dunmore Getaway — Foliage Views & Ski Retreat

Killington/Okemo, 7p Hot tub, Spacious, Mtn.views!

Sky Zen - Ridgeline Retreat

Willard Haus | Hot Tub | 3BD • 3BA | Quiet

Fred Eddy Farmhouse

Cheerful two bedroom home with a fire pit.
Condo rentals with a patio

Luxury Condo - with Garage Parking and Pool

Main St Escape | Explore Downtown Ludlow

Killington Condo-Indoor Pool/HotTub/FitnessCenter

POW value in this Cozy 2 Bedroom .2 mi to lift

Killington Getaway 2bed/1.5 bath

Ground Floor, Okemo True Ski-in/Ski-Out

Mountain Hideaway two bedroom condo Near PICO MTN

Luxury, downtown apt w/ balcony close to skiing
When is the best time to visit Pittsfield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ1,645 | ﺩ.ﺇ1,612 | ﺩ.ﺇ1,396 | ﺩ.ﺇ1,131 | ﺩ.ﺇ1,131 | ﺩ.ﺇ1,113 | ﺩ.ﺇ1,161 | ﺩ.ﺇ1,113 | ﺩ.ﺇ1,131 | ﺩ.ﺇ1,238 | ﺩ.ﺇ1,131 | ﺩ.ﺇ1,469 |
| Avg. temp | -7°C | -6°C | 0°C | 7°C | 14°C | 18°C | 21°C | 20°C | 15°C | 9°C | 3°C | -3°C |
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.ﺇ514 per night before taxes and fees

Verified guest reviews
Over 2,410 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
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!
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- Rentals with a patio Rutland County
- Rentals with a patio Vermont
- Rentals with a patio United States
- Lake George
- Okemo Mountain Resort
- Stratton Mountain
- Sugarbush Resort
- Killington Resort
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Bolton Valley Resort
- Fort Ticonderoga
- Bromley Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Fox Run Golf Club
- Montshire Museum of Science
- Mount Sunapee Resort
- Adirondack Extreme Adventure Course
- Dartmouth College
- Trout Lake
- Southern Vermont Arts Center
- Shelburne Vineyard
- Shelburne Museum
- Middlebury College
- Quechee Gorge
- Warren Falls




