Vacation rentals with a patio in Pioneer Valley

Find and book unique accommodations with an outdoor patio on Airbnb

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Popular amenities for Pioneer Valley accommodations with an outdoor patio

Apartment rentals with a patio

Top guest favourite
Apartment in Northampton
4.95 out of 5 average rating, 100 reviews

Downtown 2BR 1.5 Bath Townhouse Charm

CaitlynRating, 5 stars2 weeks ago
Andrew’s place is perfect! We stayed for an old friend’s wedding and the location couldn’t have been better - safe quiet neighborhood that was walkable to everything! The space is clean and well-stocked with easy parking and comfy amenities. We were especially grateful for the easy check-out after a late night of catching up with old friends. :-) Highly recommended this host for your stay in Northampton!
Top guest favourite
Apartment in North Adams
4.99 out of 5 average rating, 108 reviews

Historic Victorian - Entire 3rd floor

CarlaRating, 5 stars2 weeks ago
We loved staying here! It was comfortable and lovely. We especially enjoyed starting and ending our days on the spacious deck enjoying the wonderful views. It was a very easy walk to Mass MOCA. We loved the recommendations we got for things to do in the area. We hope to stay here every time we go to Mass MOCA.
Top guest favourite
Apartment in Charlemont
4.99 out of 5 average rating, 157 reviews

Suite 23 - Spacious Sunny 2-BR with Mountain view

MichelleRating, 5 stars1 month ago
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!
Guest favourite
Apartment in Great Barrington
4.92 out of 5 average rating, 102 reviews

Berkshire Retreat|King Bed|Wi-Fi|2m Ski Resort

MelanieRating, 5 stars3 weeks ago
Enjoyed our stay at The Lantern House. The room was great with updated amenities, comfortable bed & nice bathroom. Thank you!
Guest favourite
Apartment in North Adams
4.92 out of 5 average rating, 101 reviews

Frankie’s Place - A Mass MoCA Neighborhood 2BR APT

LoganRating, 5 stars1 month ago
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
Superhost
Apartment in Northampton
4.83 out of 5 average rating, 116 reviews

Florence ctr 1br apt near town, trails, river!

TameezaRating, 5 stars1 week ago
We had a great stay. Bruno’s place is quiet and very comfortable. It worked very well for us during our Northampton trip. Host is communicative and accommodated our needs.
Superhost
Apartment in West Springfield
4.87 out of 5 average rating, 38 reviews

Cozy First-Floor Retreat with Modern Comforts

EstherRating, 5 stars1 month ago
This was the perfect place to stay for our visit to West Springfield. It had everything we needed and Vasily was super helpful with any questions and provided super clear instructions. 10/10 do recommend.
Superhost
Apartment in Holyoke
4.84 out of 5 average rating, 129 reviews

Quiet bright & sunny 2 bedroom apartment w/ porch

SarahRating, 5 stars1 month ago
It was a great experience, very easy to get to.Super clean we enjoyed our stay!!

House rentals with an outdoor patio

Guest favourite
Home in Northfield
5 out of 5 average rating, 8 reviews

Minimalist forest retreat

JoseRating, 5 stars7 months ago
We had a great stay at Sally and Noava’s place! The surroundings were so peaceful and beautiful, truthfully a cabin in the woods. The house was perfectly clean and relaxing. The hosts were so responsive making it that much more comfortable of a stay. We would definitely come back here again!
Superhost
Home in Keene
4.75 out of 5 average rating, 4 reviews

2 Master Suites, Hot Tub, Walking to Downtown.

StephenRating, 5 stars9 months ago
Behind an unassuming exterior façade, the interior was truly remarkable from an interior design and furnishing perspective. Not only were the furniture, linens and glassware spectacular, The overall result was a beautiful and tranquil retreat. We were super impressed and would love to return.
Guest favourite
Home in Springfield
4.85 out of 5 average rating, 27 reviews

3 Bedroom Home Quiet Area

CatherineRating, 5 stars2 months ago
Our work crew said that they found Bob's place full of old-world charm while also providing all the modern necessities. If you're looking for a hip TikTok hang, this may not be the place for you, but if what you want is a clean, comfortable home for relaxing or remote work, Bob's place is highly recommended. It was a welcome respite from long workdays. Bob was easy to work with and the photos are an accurate presentation of the space. Bob even made sure the drive and walk areas were snow and ice free during their stay. Thanks Bob!
Top guest favourite
Home in Torrington
5 out of 5 average rating, 23 reviews

Quiet and Cozy Getaway

JenniferRating, 5 stars1 month ago
We loved our stay at Sahra's place! Not only is it exactly as pictured, we really appreciated the extra touches like the tea selection and thoughtful goodies which made us feel at home. The house is very clean. The sofa and chair are very comfortable and recline which makes for relaxing TV-watching, a nice touch. Sahra is very personable and responsive which we loved - she even brought us some of her yummy homemade goodies! We will definitely return.
Superhost
Home in Granby
5 out of 5 average rating, 4 reviews

Countryside Cape- Entire Home

BruceRating, 5 stars2 months ago
Nice clean house with large rooms in a convenient location.
Superhost
Home in North Adams
4.89 out of 5 average rating, 109 reviews

Central Haus (Group getaway on a quiet street)

MichelleRating, 5 stars1 week ago
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!
Guest favourite
Home in Ellington
4.82 out of 5 average rating, 62 reviews

Cheerful 3 bedroom home with large back yard

SijoRating, 5 stars5 days ago
Our stay at Andy's home was absolutely wonderful! The place was exactly as described—spotlessly clean, beautifully decorated, and fully equipped with everything we needed. The host was incredibly welcoming, responsive, and thoughtful throughout our stay. The location was perfect—peaceful yet conveniently close to shops and attractions. We truly felt at home and would not hesitate to book again. A small suggestion is to repair the locks of the bedrooms.
Guest favourite
Home in Pittsfield
4.96 out of 5 average rating, 54 reviews

Charming lake home with amazing sunset views

WilliamRating, 5 stars4 months ago
My girlfriend and I spent four nights days at Joe and Jess’s beautiful home for a much needed vacation after the holidays. We spent most of our days/nights in the sunroom playing board games and watching movies with the beautiful view of the lake. It snowed halfway through our stay and the snow on the lake made it truly feel like we were in a winter wonderland. The house was very clean and we had everything we needed to cook our meals. We would love to come back during the warmer months and explore the lake as well as some of the hiking trails nearby.

Condo rentals with a patio

Guest favourite
Condo in Litchfield County
4.95 out of 5 average rating, 21 reviews

Pacer's Pasture

CerayeRating, 5 stars4 months ago
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!
Top guest favourite
Condo in Wilmington
5 out of 5 average rating, 12 reviews

Ski2Tee

JamesRating, 5 stars6 months ago
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 .
Superhost
Condo in Hartford
4.82 out of 5 average rating, 17 reviews

Spacious Condo Near Everything • BizLeisure

DianaRating, 5 stars3 months ago
Always happy to come back!
Guest favourite
Condo in Hancock
4.95 out of 5 average rating, 58 reviews

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base

EladRating, 5 stars2 weeks ago
A Perfect Stay at Elisa's! Elisa's place was absolutely magical! Located in a charming yet convenient resort, this beautifully designed space instantly felt like home. Sunlight streams through the windows, illuminating tasteful décor that balances style and comfort. What truly stands out is Elisa's hospitality. Her communication was warm and helpful, and her local recommendations led us to hidden gems throughout the area. The spotless cleanliness and private garden oasis for morning coffee or evening drinks made everything perfect. This place represents exceptional value—not just accommodation but an experience connecting you to the local community.
Guest favourite
Condo in Lenox
4.97 out of 5 average rating, 33 reviews

Spacious 3 bedroom apt in Lenox historic downtown

ThomasRating, 5 stars4 months ago
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.
Condo in Hancock
4.88 out of 5 average rating, 33 reviews

Unique - Country suite @ Jiminy Peak

BrentRating, 5 stars15 months ago
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+
Superhost
Condo in Shelburne Falls
4.91 out of 5 average rating, 46 reviews

Flowers & Falls Spot House

MelanieRating, 5 stars2 months ago
Superhost ! Was so accommodating to get us in last minute since our other Airbnb didn’t work out. He was so responsive and helpful with the snow storm as well ! We were so glad to have found this gem and have such a gracious host. The location is perfect and walkable to all the restaurants and markets. Also 15 mins away from Berkshire East ! This was a great find and we are thankful for it !
Superhost
Condo in Adams
4.75 out of 5 average rating, 40 reviews

Downtown Adams Vintage Getaway

ChristyRating, 5 stars1 week ago
Ashley has a great place!! It was a fantastic place to visit with my friends and reminisce. Weirdly, this rental turns out to be the place my great grandparents lived and did business as my grandma grew up. I did not have any ghostly contact with my relatives in the apartment (I was kind of hoping and not hoping to see them 😂), but I still had such a meaningful time sitting in the spaces they did so many years ago. Ashley is an excellent host and I will come here again next time I “come home”. 😊

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