
Vacation rentals with a patio in Pittsfield
Find and book unique accommodations with an outdoor patio on Airbnb
Top-rated accommodations with an outdoor patio in Pittsfield
Guests agree: these accommodations with an outdoor patio are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Pittsfield accommodations with an outdoor patio
Apartment rentals with a patio

Studio Oasis nr Warren St w porch & yard
Beautiful spacious studio. Very clean and decorated very nicely. Short walk to Warren St shops and restaurants.

Historic Victorian - Entire 3rd floor
Loved our short stay in this cozy space! Walked to downtown North Adams and Mass MOCA — I didn’t realize this Airbnb was so close until we arrived which was awesome! And the bed was sooo comfortable.

Lovely 1 bedroom suite in historical house
We had a wonderful stay! Emily's space is super cozy and comfortable. Seamless check-in and check-out as well :)

Suite 23 - Spacious Sunny 2-BR with Mountain view
We had another wonderful weekend at Barbara & Chad's suite. We've stayed there multiple times and love it for our family of four. The hosts are always responsive and so very helpful. We also love the nearby Berkshire East Mountain resort and nearby local towns. Looking forward to our next visit!

Catskill Village House - Studio w/ Private Terrace
Lovely place. Perfect location to enjoy the nearby hicking trails and Kaaterskil Falls, while walking distance to coffee shops and restaurant in Catskill. Liked the decorations and the little terrace.

Berkshire Retreat|King Bed|Wi-Fi|2m Ski Resort
We had a great stay!! It was the perfect spot for an overnight. We loved the area and especially appreciated their recommendations! Hopefully next time we can stay longer and see even more!

Frankie’s Place - A Mass MoCA Neighborhood 2BR APT
Very happy with our stay at Frank’s in North Adams. Super friendly host and perfect place to enjoy a mixed bag of weather, mostly decent for early April, easy and content to both go out to see the city and just stay in to hang out in the three season porch or watch a movie. Great recommendations from our host for outdoor places to check out. Walkable. Peaceful. Would hope to stay here again

An Apartment with a View
We loved our stay! The apartment was comfortable and private. The location was serene and calm. Maura was an excellent host. It was a great home away from home!
House rentals with an outdoor patio

Albany 2 Bedroom House
This was the first Airbnb I ever stayed at, and it was absolutely amazing! it was very clean and we really enjoyed our stay here. It is a nice safe neighborhood and area. if we ever came back out that way, we would definitely stay here again. this was the ideal home. Very cute & convenient set up

Beautiful, cozy house for rent
Lovey home and very convenient location in Willamstown. Would highly recommend.

Countryside Cape- Entire Home
Nice clean house with large rooms in a convenient location.

Townhouse in Hudson 2 minute walk to Warren ST
We had a great time. We walked to restaurants and shopping. I loved the antiques and the Lincoln theme. The place was very clean. It snowed over night 5 inches. We could not find a shovel. It was the last day, so we were packing and loading car, not that big of a deal. Also because of our love for the antiques, coasters would have been helpful. Again not that big of a deal. We really liked the place and the location. Thanks, Kim

Central Haus (Group getaway on a quiet street)
Great stay at Mian and Anthony's place. Kitchen was well stocked with everything we needed, there was tons of space, and comfy beds. We are grateful that they allowed us an early check in too. Would stay with them again gladly!

2-bedroom home steps away from town
Great stay in Hudson. Austin’s place was the perfect crash pad while we explored Hudson. The place was stocked with everything we needed and more. Very comfortable and home-y. Would 100% stay again on my next visit to Hudson!

Best of the Berkshires + Hot Tub by Evergreen Home
This is a good example of what you should expect from a well run and thoughtfully put together Airbnb. everything was well done. little touches in the house make a difference and just feels better. I can see how a second privacy screen in the hot tub area could give a bit more privacy, but not a big deal. great spot. highly recommended.

Modern home, King Bed 4 bed 2bath, Crib, parking
The place was beautifully clean and comfortable. We were 4 adults, one child, and a toddler. There were plenty of towels. Everything was easy to keep clean.
Condo rentals with a patio

Cozy 2BR Condo Walking Distance to Mount Snow
Think this is our third time staying at the condo and again it was great. Love being able to walk across the street to the mountain, renting equipment from Equip Sports is very convenient. In our opinion the condo has everything you need for a family of 4. Can’t wait until next year.

Ski2Tee
The home was perfect and the location was great to use as a base to explore fall colors and the small towns of southern Vermont .

Slopes N Seasons | Trailside Condo at Mount Snow
We loved our stay! Everything was immaculate. New. Even ready with some fun board games and a Bluetooth speaker. The location was excellent, and we had a great time! We definitely recommend and would stay again.

Cozy Mnt Snow Condo - *4 Min walk to Lift*
I enjoyed my stay at Caitlyn and Joey's place. It was just a short walk from both the Equipe sports store and the Mount Snow Sundance lift, the latter being a great starting point for days on the mountain. Next to the lift is a waffle cabin, which made for a tasty post-mountain snack. The apartment was clean, the fireplace toasty, and the hosts responsive. I'd definitely recommend staying here, and am looking forward to staying here again myself!

Ski in/out - 2BR Condo - Indoor Pool/Spa
Great condo at Mt Snow. Very clean and organized. Location is on the mountain. It requires some steep walking for ski in/ski out so keep in mind for younger kids while also carrying their gear. My kids are older so it wasn’t an issue for us but worth mentioning. Eric is the perfect host - always reachable and responsive. Super accommodating when he’s able to be. We got unlucky wind hold weather and he offered to extend our check out if we wanted to ski an extra day to make up for it. Truly awesome. Can’t go wrong.

Condo w/ great amenities 4-seasons! Ski in Ski out
Christine is very easy to work with and very responsive. she answered us back right away before and during our stay. the place is great! very cozy and comfortable. I can't wait to go back to her place next time we're in town!

Seasons on Mount Snow | Walk Out / Ski Home!
It was exactly how described by management and pics. We felt at home and kitchen had everything one needs. Greg the manager was incredibly responsive and professional…. We would go back.

Cozy Condo-4 Minute Walk to Skiing at Mount Snow!
We had a great late season long ski weekend at Elizabeth’s condo at Mount Snow and would definitely recommend this place to others. It was clean and cozy and we had good communication with the host. The condo wasn’t the most renovated but it was clean and comfortable, had all of the desired amenities (dishwasher, washer/dryer, fireplace, good heating system, large comfy couch, and two full bedrooms and bathrooms with a third loft room) and had more than enough space for our group of four. We were able to easily walk in about 5 min to the Sundance parking lot and lift (only open during the weekend during our trip). Elizabeth sent some good restaurant recommendations as well. We hope to come back soon! Thank you for a great trip!
Quick stats about vacation rentals with a patio in Pittsfield
Total rentals
130 properties
Nightly prices starting at
$55 CAD before taxes and fees
Total number of reviews
5.6K reviews
Family-friendly rentals
90 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
20 properties have a pool
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- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Catamount Mountain Ski Resort
- Albany Center Gallery
- Six Flags New England
- Berkshire East Mountain Resort
- Taconic State Park
- Mount Snow Ski Resort
- Mohawk Mountain Ski Area
- Zoom Flume
- Mount Greylock Ski Club
- John Boyd Thacher State Park
- Mount Sugarloaf State Reservation
- Bash Bish Falls State Park
- Norman Rockwell Museum
- Opus 40
- Kent Falls State Park
- Bousquet Mountain Ski Area
- Otis Ridge
- Naumkeag
- Beartown State Forest
- Ekwanok Country Club
- Bright Nights at Forest Park
- Talcott Mountain State Park