
Vacation rentals with a patio in Stockbridge
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Apartment rentals with a patio

Studio Oasis nr Warren St w porch & yard
We loved staying at Janet’s place. And would stay here again. The studio is beautiful, comfortable and spacious and had everything we needed. We loved the clawfoot tub and shower. It is truly is a special place to stay. It was a quick walk to Warren Street and to Amtrak trains. Thank you for being a great host.

Historic Victorian - Entire 3rd floor
Our stay couldn’t have been better. The listing matched reality perfectly—stairs and all—and the hosts stayed a step ahead with friendly, detailed messages and a useful house guide. The location is superb: an easy stroll to everything in North Adams and a great jumping-off point for exploring the Berkshires. The home itself was spotless, cozy, and wonderfully quiet. The hosts were extremely understanding of a minor issue (our fault) that occurred. We thoroughly enjoyed our visit and would gladly return.

Lovely 1 bedroom suite in historical house
We enjoy old houses, so we found Emily's house a gem. It is a beautifully renovated space that includes modern conveniences but leaves the beautiful old doors and floors to give depth and beauty to the space.

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 - The Loft
We had a great time at the Catskills and enjoyed our stay comfortably at the Catskills Village. We didn't bring a car and were able to explore the town by walking and Ubering to Hudson (with a wait time, as expected). Tommy and Jenna gave us some recommendations, which made planning for the trip easier. The space was perfect for two, with the bathroom on the second floor and the bedroom on the third floor. Everything was as described (we loved the interior design!) and perfect for a weekend getaway. Great location for a peaceful time away from the big city. Thank you Tommy and Jenna!

The Ivy on the Stone
We had a wonderful stay at Katherine’s beautiful cottage in Kingston. The home was cozy, clean and thoughtfully decorated ~ truly a perfect retreat. Surrounded by nature, the peaceful setting made it easy to relax and unwind. Katherine was a warm and responsive host, making everything seamless from start to finish. Highly recommended for anyone looking to enjoy the charm of the Hudson Valley!

Frankie’s Place - A Mass MoCA Neighborhood 2BR APT
Really clean and perfect for what we needed it for! We were there to move out our daughter from Williams College and it worked out perfectly.

Hudson River Beach House
We had a good time. This was a great place with beautiful views!
House rentals with a patio

Cozy remodeled home with all the modern amenities
We had a lovely time at this airbnb. It was fun to walk around the neighborhood and feel safe. There were kids everywhere and we were able to walk to the playground easily. The home was very nice. The beds were comfortable and the main bedroom even had black out shades and each room had a sound machine. Yay sleep! It was clean and felt like home. Would return no problem.

Whispering Woods Guest House
Taylor's space was exactly as described. Decorated so cute and extremely clean. Excellent amenities including well-appointed kitchen, snacks, coffee, tea, robes and slippers. Water pressure (including hot water) more than adequate. Tons of info available for "out of towners" if necessary. Communication was top notch.... accommodating, friendly and practically instantaneous. Would highly recommend. Thank you Taylor and Robert!!!

Cambridge Hill Farmhouse - Sauna - Swimming Pond
My stay at Danielle’s was so lovely, the swimming pond was so special and just created a beautiful atmosphere around the backyard. The place itself had so much character in the kitchen was greatly stocked. The sauna was lovely and could not get over the view that it had it was raining for most of my trip, but it didn’t take away from the beauty of the place. We were very grateful for how accommodating Danielle was for our arrival and departure. A heads up for anyone that is over 6 foot you will have to duck your head for every bathroom haha would not stop us from booking again though! Such a real gem!

Lenox Cottage
The local can't be beat! Easy to walk to downtown shops and restaurants. Other major attractions are close by, and you can even walk to Kripalu if need be. The home felt like a home with unique decor and a great layout. Would love to stay again!

The Red House
Leslie's house was wonderful. Comfortable home with lots of space in a peaceful setting. Beautiful views and walking distance to a bird sanctuary with nice trails. We would love to stay here again.

Historic Stone Church in The Berkshires
Our stay at Hinterland Hall was a wonderful, unique experience. The property has been carefully restored and tastefully staged. The surrounding area includes some great hikes, like Mount Graylock to the north and Monument Mountain to the south.

Cheerful Catskill Village Cottage
We loved this cozy spot! Great location, very centralized and close to everything. Margaret was a great host and very responsive. Definitely keeping this spot for future visits!

Lakefront Retreat -Private Dock,creek,and Fire pit
Had a beautiful, relaxing stay with friends at George's place right on the lake. Loved sitting on the deck watching trout swim in the stream and deer passing by. The house is in a perfect location, short drive to both downtown Lenox and Lee. In addition, the house is right down the street from High Lawn farm which makes delicious ice cream and cheese. Can't wait to visit again!
Condo 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!

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

Spacious 3 bedroom apt in Lenox historic downtown
Yulia's place was the perfect spot for a Memorial Day weekend getaway. Was even great for an infant! It was comfy and cozy! Loved the patisserie downstairs and the town. Highly recommend!

Hudson Valley Hiker’s Loft-Private Room Queen Bed
I had a great stay! Super comfortable bed, room had everything I needed, and the AC unit kept my room very comfortable on the 90 degree day! Henry & Jorge were both very kind and easy to be around. If you're looking for a comfy bed in a comfortable space, this is perfect!

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+

Flowers & Falls Spot House
Always an easy peaceful stay whenever we stay at David’s place. We will be back again

Downtown Adams Vintage Getaway
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”. 😊

Cozy private bedroom in 2nd floor apartment
Luke is a great person with an amazing personality. If you have any questions, just communicate with him and he will take care of everything else. Have a bless day everyone!!
Quick stats about vacation rentals with a patio in Stockbridge
Total rentals
70 properties
Nightly prices starting at
ﺩ.ﺇ294 before taxes and fees
Total number of reviews
3.3K reviews
Family-friendly rentals
60 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
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- Hunter Mountain
- Six Flags New England
- John Boyd Thacher State Park
- Jiminy Peak Mountain Resort
- Windham Mountain
- Albany Center Gallery
- Bushnell Park
- Bash Bish Falls State Park
- Taconic State Park
- Catamount Mountain Ski Resort
- Zoom Flume
- Kent Falls State Park
- Mount Greylock Ski Club
- Berkshire East Mountain Resort
- Hunter Mountain Resort
- Mohawk Mountain Ski Area
- Norman Rockwell Museum
- Bright Nights at Forest Park
- Hartford Golf Club
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Bousquet Mountain Ski Area
- Opus 40
- Naumkeag