
Holiday rentals with a patio in Pittsfield
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Top-rated rentals with patio in Pittsfield
Guests agree: these rentals with a patio are highly rated for location, cleanliness and more.
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Popular amenities for rentals with patio in Pittsfield
Flat rentals with a patio

Studio Oasis nr Warren St w porch & yard
The perfect stay. Clean, comfortable, very responsive host, great location, studio perfect for two of us - all contributed to a wonderful weekend away. We’d love to return here next time in Hudson.

Historic Victorian - Entire 3rd floor
Spacious stay, wonderfully clean and quiet and an excellent view from the balcony. Lots to see and do in the area. It got a bit cold in the bedroom at night - advise packing some warm pajamas if traveling in the colder seasons!

Two bedroom close to colleges!
Great place… clean and had everything we needed. Allen is very accommodating and responsive whenever we contacted him. We would definitely stay there again.

Lovely 1 bedroom suite in historical house
Really lovely. Emily’s space was perfect for us, comfortable, clean, great location. And Emily was always responsive making it easy to communicate as needed. I hope we’ll have the opportunity to return next time we’re in the area. Highly recommend.

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!

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!

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!

Hudson River Beach House
This was the perfect spot and location for a getaway with my girlfriend. The unit is beautiful, clean and you can’t beat the view of the Hudson.
House rentals with a 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
A truly cozy and thoughtful retreat. This house anticipated every need. The host created such a welcoming, hygge vibe—perfect for relaxation and feeling at home. I felt truly taken care of during my stay. A peaceful, well-thought-out getaway. (The vinyl ready to go was a lovely detail.)

Modern home, King Bed 4 bed 2bath, Crib, parking
Perfect size house in a great location. House was professionally cleaned and ready for us upon our arrival. Great parking too. Thanks for the stay!
Apartment rentals with a patio

Pacer's Pasture
Pacers Pasture is on a quiet road giving it a cute country experience in a great small town. The space has an amazing unfenced yard which was great for the dogs. Easy access inside with key entry, and we loved the door entry being toward the back of house for added privacy. The house has very comfortable linens, tons of parking, and the hottest water ever - which was perfect after a cold day adventuring. Aaron provides toiletries, some nice kitchen basics likes spices and teas/coffee, fast wifi-TV streaming, and a cozy space perfect for relaxing. Bonus points for being tastefully decorated and not overly cluttered. Would stay again!

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 .

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base
We had a wonderful stay at the condo - ideally located, spacious and comfortable and had everything we needed ! Definitely will be back! Elisabeth was generous, responsive and super friendly and excited for us for our trip!

Spacious 3 bedroom apt in Lenox historic downtown
Beautiful apartment with lots of rooms-comfy sitting areas and lots of light. It was very nicely appointed and the checkin was simple. We will definitely be back as the location is ideal.

Unique - Country suite @ Jiminy Peak
We had a fabulous time up at Jiminy Peak and being right on the mountain at Shana’s place made it very easy to enjoy the many things to do. Shana is a great host and her unit was perfect for our family of 5. Our younger two tried counting all of the gnomes in every room. We definitely recommend staying at Shana’s place, she is very easy to work with and quick to answer any questions. Thanks again A+

Downtown Adams Vintage Getaway
As described and walkable to local coffee houses and rail trail with Mass Moca a 10 minute drive away. The host was very communicative and helpful with clear directions inside the unit.

Ski Condo 5 Min from Mt Snow
Second stay at William’s. Loved it again the second time, great area and super close to Mt Snow resort. Great restaurants and of course the Snow Republic Brewery nearby. Thanks for the great stay!
Quick stats about holiday rentals with a patio in Pittsfield
Total rentals
130 properties
Nightly prices starting at
£30 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
Destinations to explore
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- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Catamount Mountain Ski Resort
- Albany Center Gallery
- Berkshire East Mountain Resort
- Six Flags New England
- Taconic State Park
- Zoom Flume
- Mohawk Mountain Ski Area
- Mount Sugarloaf State Reservation
- Opus 40
- John Boyd Thacher State Park
- Mount Greylock Ski Club
- Kent Falls State Park
- Bousquet Mountain Ski Area
- Mount Snow Ski Resort
- Bash Bish Falls State Park
- Beartown State Forest
- Otis Ridge
- Norman Rockwell Museum
- Naumkeag
- Bright Nights at Forest Park
- Peebles Island State Park
- Northern Cross Vineyard