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

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.

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.

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.

Lg Renovated Mtn View • Shuttle • Hot Tub • Xbox
Savor stunning mountain views from this oversized 1BR/1BA in Mountain Green Building 3—just a short walk or shuttle ride to Killington Resort and the tube park. Inside you’ll find a modern kitchen and bath, new flooring, cozy furnishings, plus an Xbox and arcade game. Best of all, the resort amenities are in the same building: indoor pool, hot tub, fitness center, ski shop, and restaurant. Ideal for couples, small families, or friends—your mountain escape awaits!

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 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!

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.

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.

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

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
Apartment rentals with a patio

Cozy VT 1st floor apartment

Rocky Meadow Farm

Lovely Duplex with Deck and Central Location

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
House rentals with a patio

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

Mountain Top - Fresh Pond - Killington - Hot Tub

Purple Door Cottage in the heart of Middlebury!

Cozy VT Getaway - Fully Furnished for Longer Stays

Ski, snow mobile, hiking, fun on slopes & trails!

Fred Eddy Farmhouse

Modern Retreat next to Mountain Top Inn,Killington

Fresh Snow- Luxury Cabin near Ski Areas
Condo rentals with a patio

Main St Escape | Explore Downtown Ludlow

Walk to Lifts * Hot Tubs & Pub * Sleeps 4

Killington Condo-Indoor Pool/HotTub/FitnessCenter

Your Killington Basecamp: Free Shuttle-Pool&HotTub

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

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

Killington Getaway 2bed/1.5 bath

Mountain Hideaway two bedroom condo Near PICO MTN
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 50 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 2,320 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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- Rentals with a patio Rutland County
- Rentals with a patio Vermont
- Rentals with a patio United States
- Okemo Mountain Resort
- Stratton Mountain
- Sugarbush Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Bolton Valley Resort
- Pico Mountain Ski Resort
- Fort Ticonderoga
- Cochran's Ski Area
- Bromley Mountain Ski Resort
- Dartmouth Skiway
- Whaleback Mountain
- Hildene, The Lincoln Family Home
- Dorset Field Club
- Fox Run Golf Club
- Lucky Bugger Vineyard & Winery
- Autumn Mountain Winery
- Northeast Slopes Ski Tow
- Country Club of Vermont
- Ekwanok Country Club
- Mount Sunapee Resort
- Montshire Museum of Science
- Baker Hill Golf Club
- Storrs Hill Ski Area




