
Vacation rentals with a patio in Pittsfield
Find and book unique patio rentals on Airbnb
Top-rated patio rentals in Pittsfield
Guests agree: these patio rentals are highly rated for location, cleanliness, and more.

Summit View Cottage:Apres Ski| Hot tub|Fireplace
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

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.

Camp Poe: Hot Tub+Game Room+Bar+6acres+Patio+AC
Experience the heart of the Green Mountains on our private 6 acre estate. Camp Poe at Estabrook is newly renovated while still maintaining its original Vermont charm--wide plank floors, 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, 12 foot dining tables (inside AND outside) and hot tub. 13 min to Killington Mtn, 10 to Pico & 4min to the #1 golf course in VT!

Stick Season Barn Stay Near Middlebury College
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.

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.

Updated Condo/Across From Mountain/Pool
Experience comfort and convenience in this renovated 1BR/1BA condo in Mountain Green building #3. Ideally located across from Snowshed and Ramshead lodges, it offers easy access to year-round activities. The condo features an open floor plan with a spacious living area, a fully updated kitchen, and modern finishes throughout. A free shuttle service stops at the building in winter. With all the amenities you need, this stylish retreat is the perfect getaway for all seasons!

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*

⛷☃️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.

Beautiful 1 bedroom apartment with balcony
Bienvenue chez nous! Experience comfort and modern beauty in this completely renovated apartment attached to a historic Victorian home. The one bedroom apartment has a private bathroom and your own balcony to enjoy. Close to popular skiing areas of Mt Sunapee (20 minutes) and Okemo (35 minutes), in addition to enjoying local hiking and cycling at Mt Ascutney, Moody Park, and Arrowhead.
Popular amenities for Pittsfield patio rentals
Apartment rentals with a patio

River's Bend NEW 1-bd Apt - 8 Mins to Montpelier

Little City Brick Apartment A

Cozy two bedroom near Manchester

Green Mts of VT/20 Min to Manchester

Green Mountain Collection: Cozy Vermont Haven

Spacious Home Near Heart of Middlebury Fiber Wifi

Mountain View Retreat

Charming & Peaceful Upper Valley 1BR Retreat
House rentals with a patio

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

The Green Mountain Getaway

Ideal Killington Escape! 2 Fireplaces & Sleeps 12

Cozy VT Getaway - Fully Furnished for Longer Stays

Stylish Ascutney Cabin with Mountain Views

Modern Cabin in Lakes Region

Charming and Centrally Located Waitsfield Home.

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

Main St Escape | Explore Downtown Ludlow

¤5-15 Mins to Ski Slopes | Fast WiFi | Fireplace¤

Killington Condo-Indoor Pool/HotTub/FitnessCenter

Ski in Cozy 2 Bedroom only 1/2 mile to Mtn & Apres

Mountain Hideaway two bedroom condo Near PICO MTN

Sugarbush Ski in / Ski Out 1 Bedroom Condo

Luxury, downtown apt w/ balcony

Lovely 1-Bedroom condo with indoor fireplace!
When is the best time to visit Pittsfield?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$93,792 GYD | G$91,908 GYD | G$79,556 GYD | G$64,482 GYD | G$64,482 GYD | G$63,435 GYD | G$63,645 GYD | G$62,389 GYD | G$62,179 GYD | G$70,554 GYD | G$64,482 GYD | G$83,743 GYD |
| 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 G$29,310 GYD 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!
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Long Island Vacation rentals
- Boston Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- Mount Pocono Vacation rentals
- Quebec City Vacation rentals
- The Hamptons Vacation rentals
- Capital District, New York Vacation rentals
- Rentals with outdoor seating Pittsfield
- Rentals with a washer and dryer Pittsfield
- Rentals with a fireplace Pittsfield
- House rentals Pittsfield
- Family-friendly rentals Pittsfield
- Rentals with a fire pit Pittsfield
- Pet-friendly rentals Pittsfield
- Rentals with a patio Rutland County
- Rentals with a patio Vermont
- Rentals with a patio United States
- Stratton Mountain
- Okemo Mountain Resort
- Sugarbush Resort
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Bolton Valley Resort
- Fort Ticonderoga
- Dartmouth Skiway
- Cochran's Ski Area
- Pico Mountain Ski Resort
- Dorset Field Club
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Autumn Mountain Winery
- Lucky Bugger Vineyard & Winery
- Whaleback Mountain
- Northeast Slopes Ski Tow
- Fox Run Golf Club
- Baker Hill Golf Club
- Ekwanok Country Club
- Montshire Museum of Science
- Mount Sunapee Resort
- Cozy Cottages & Otter Valley Winery
- Country Club of Vermont