Holiday rentals with a patio in Stockbridge

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Popular amenities for rentals with patio in Stockbridge

Flat rentals with a patio

Guest favourite
Flat in Hudson
4.97 out of 5 average rating, 177 reviews

Studio Oasis nr Warren St w porch & yard

CharleneRating, 5 stars2 days ago
Beautiful studio with everything you need for a trip to Hudson! I wish I could have stayed longer. Janet was a wonderful, responsive host.
Top guest favourite
Flat in North Adams
4.99 out of 5 average rating, 110 reviews

Historic Victorian - Entire 3rd floor

LaurenRating, 5 stars3 weeks ago
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.
Guest favourite
Flat in Saugerties
4.92 out of 5 average rating, 338 reviews

Saugerties Village home with great backyard!

JenniferRating, 5 stars4 weeks ago
John and Emma's place is exactly as described. It is neat and comfortable. You can tell they put a lot of care into making the place feel welcoming. It is on a busy corner so that might be off-putting to some, but it was fairly quiet on the days we were there. You are able to walk to town to many restaurants, shops, and ice cream and there is a big grocery store just down the road.
Guest favourite
Flat in Coxsackie
4.93 out of 5 average rating, 134 reviews

Lovely 1 bedroom suite in historical house

LakeRating, 5 stars2 weeks ago
Our 2nd time staying here and it was as fantastic as the first!
Top guest favourite
Flat in Charlemont
4.99 out of 5 average rating, 158 reviews

Suite 23 - Spacious Sunny 2-BR with Mountain view

MichelleRating, 5 stars3 months 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
Flat in North Adams
4.92 out of 5 average rating, 107 reviews

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

AnnaleeRating, 5 stars3 weeks ago
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.
Top guest favourite
Flat in Hudson
4.97 out of 5 average rating, 144 reviews

Restored 19th century farm house apartment

WilliamRating, 5 stars3 weeks ago
Beautiful environment and super welcoming hosts. A great experience!
Guest favourite
Flat in Craryville
4.92 out of 5 average rating, 137 reviews

Captain's Quarters at Mickey's Marina

CarlRating, 5 stars1 week ago
We had a great say. Beautiful area. Tremendous lake which we enjoyed by kayak. Rooms were clean and comfortable. Nice sitting area outside and another on the front porch. We were here early June and so the eatery next store and another up the road were not open for the season quite yet. Great communication.

House rentals with a patio

Top guest favourite
Home in Canaan
4.96 out of 5 average rating, 54 reviews

Private Retreat: Hot Tub! Movie Room! Pool Table!

MusserRating, 5 stars1 week ago
This was a bit of a last minute decision to come to the Berkshires and I was grateful that Tiffany could accommodate some quick changes. The house is just as described--lots of space, nice setting, pool table was fun (and cool in the basement), and I appreciated that our two dogs could be included. Even though the house is in NY, it is not far from the hiking trails and museums. We would like to come back--a lot more to see and do in this area.
Top guest favourite
Home in Hillsdale
5 out of 5 average rating, 51 reviews

Cambridge Hill Farmhouse - Sauna - Swimming Pond

janetRating, 5 stars3 days ago
This was a perfect vacation home for our family trip. Spacious house with beautiful indoor and outdoor spaces, a well equipped kitchen, luxurious and extremely comfortable furnishings and a location that makes visits to surrounding charming towns so easy.
Guest favourite
Home in Great Barrington
5 out of 5 average rating, 11 reviews

Valley Vista atop Jug End

PanosRating, 5 stars1 week ago
Nice place. Great layout. Easy to navigate. Host was very communicative. We would stay there again.
Guest favourite
Home in West Stockbridge
4.98 out of 5 average rating, 54 reviews

Berkshires Forest Retreat with Hot Tub

SarahRating, 5 stars4 weeks ago
The house was a great place to spend a weekend with family and friends. Very comfortable with a baby. We loved the outdoor space and Annie was very responsive when we needed help.
Guest favourite
Home in Hudson
4.96 out of 5 average rating, 156 reviews

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

ChristopherRating, 5 stars3 weeks ago
Very enjoyable time here! Instructions, accommodations, and overall experience was perfect!
Top guest favourite
Home in Old Chatham
4.98 out of 5 average rating, 48 reviews

The Red House

SandyRating, 5 stars3 weeks ago
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.
Guest favourite
Home in Great Barrington
4.97 out of 5 average rating, 32 reviews

Charming Cottage - Walk To Town

AmandaRating, 5 stars2 months ago
Perfect location for a few friends that came for a birthday party. Was perfect. I didn’t worry about them at all, and I knew they had a quality stay
Top guest favourite
Home in Catskill
4.97 out of 5 average rating, 150 reviews

Cheerful Catskill Village Cottage

EmilioRating, 5 stars2 weeks ago
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!

Apartment rentals with a patio

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

Pacer's Pasture

CerayeRating, 5 stars5 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!
Guest favourite
Apartment in Hancock
4.95 out of 5 average rating, 59 reviews

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

EladRating, 5 stars1 month 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
Apartment in Lenox
4.97 out of 5 average rating, 34 reviews

Spacious 3 bedroom apt in Lenox historic downtown

JamieRating, 5 stars3 weeks ago
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!
Guest favourite
Private room in Saugerties
4.88 out of 5 average rating, 183 reviews

Hudson Valley Hiker’s Loft-Private Room Queen Bed

KristinRating, 5 stars1 week ago
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!
Apartment in Hancock
4.88 out of 5 average rating, 33 reviews

Unique - Country suite @ Jiminy Peak

BrentRating, 5 stars17 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
Apartment in Shelburne Falls
4.92 out of 5 average rating, 48 reviews

Flowers & Falls Spot House

TerriRating, 5 stars2 weeks ago
Always an easy peaceful stay whenever we stay at David’s place. We will be back again
Superhost
Apartment in Adams
4.74 out of 5 average rating, 42 reviews

Downtown Adams Vintage Getaway

ChristyRating, 5 stars1 month 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”. 😊
Private room in Troy
4.83 out of 5 average rating, 6 reviews

Cozy private bedroom in 2nd floor apartment

MohsinRating, 5 stars2 months ago
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 holiday rentals with a patio in Stockbridge

  • Total rentals

    70 properties

  • Nightly prices starting at

    $102 SGD 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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