Vacation rentals with a patio in Stockbridge

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Popular amenities for Stockbridge patio rentals

Apartment rentals with a patio

Guest favorite
Two turquoise Adirondack chairs are positioned on a grassy area, facing the entrance of a light blue house. Lush foliage surrounds the space, with trees and colorful shrubs enhancing the natural setting. A private porch features white railings, adding architectural interest.
Apartment in Hudson
4.97 out of 5 average rating, 174 reviews

Studio Oasis nr Warren St w porch & yard

SharonRating, 5 stars2 weeks ago
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.
Guest favorite
A cozy studio space features a full-size bed with a neutral comforter, a desk and chair set against a wall, and a small television mounted above a radiator. Natural light enters through a window, with patterned curtains framing the view. The bathroom doorway is visible in the background.
Apartment in Amenia
4.92 out of 5 average rating, 105 reviews

Amenia Main St Cozy Studio

AvocetRating, 5 stars3 weeks ago
Cute, cozy, clean, and super close to the bike trail! Perfect stay for a weekend exploring the towns along the trail.
Top guest favorite
A balcony deck is depicted with two blue Adirondack chairs facing a small round table. A floral centerpiece is placed on the table, which is accompanied by two glasses. The area is surrounded by lush green trees, creating a serene atmosphere.
Apartment in North Adams
4.99 out of 5 average rating, 110 reviews

Historic Victorian - Entire 3rd floor

LaurenRating, 5 stars2 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 favorite
A historic Greek Revival house is seen from the front yard, featuring a white facade complemented by green trees. A red door serves as a focal point, with several windows allowing natural light. The yard is bordered by a wooden fence and includes well-maintained grass.
Apartment in Coxsackie
4.92 out of 5 average rating, 132 reviews

Lovely 1 bedroom suite in historical house

CristinaRating, 5 stars1 month ago
Emily’s place was cute and charming. She was super responsive and had lots of helpful recommendations for the area. The house was a short distance from town, easily walkable. Easy check in and check out as well!
Top guest favorite
A modern kitchen features a central island with bar stools, stainless steel appliances, and white cabinetry. Natural light floods the space through a skylight and large windows, highlighting the open layout. A dining area with dark chairs sits adjacent to the kitchen.
Apartment in Charlemont
4.99 out of 5 average rating, 158 reviews

Suite 23 - Spacious Sunny 2-BR with Mountain view

MichelleRating, 5 stars2 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 favorite
A cozy bedroom features a spacious bed with light grey bedding, accompanied by a side table and a soft glow from a nearby lamp. Sunlight filters through sheer white curtains, illuminating the warm wood floor. A doorway leads to the private bathroom, visible on the right.
Apartment in Catskill
4.94 out of 5 average rating, 150 reviews

Catskill Village House - Studio w/ Private Terrace

ElizaRating, 5 stars3 weeks ago
Second time back at this spot! This stay was just as great as the first! Hope to be back soon!
Top guest favorite
A cozy bedroom features a spacious bed with layered bedding. A gallery wall of framed art pieces adds visual interest. Natural light filters through a window with shutters, illuminating the warm wood floors. An electric fireplace and a potted plant provide a touch of comfort.
Apartment in Kingston
4.96 out of 5 average rating, 256 reviews

The Ivy on the Stone

AliRating, 5 stars1 week ago
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!
Top guest favorite
A circle of wooden Adirondack chairs surrounds a fire pit, situated on a sandy area near the riverbank. Lush greenery and trees frame the space, while a modern two-story house can be seen in the background, blending with the natural landscape.
Apartment in Coxsackie
5 out of 5 average rating, 113 reviews

Hudson River Beach House

KristinaRating, 5 stars1 month ago
So peaceful. Clean and relaxing. I already recommended it to somebody.

House rentals with a patio

Guest favorite
Home in Great Barrington
4.93 out of 5 average rating, 42 reviews

Cozy remodeled home with all the modern amenities

LaurenRating, 5 stars1 month ago
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.
Guest favorite
A cozy seating area features an orange sofa adorned with decorative pillows in various patterns. The walls are accented with framed artwork and shelves displaying decorative items. Black curtains frame a window, allowing natural light to brighten the space.
Home in Pittsfield
4.95 out of 5 average rating, 20 reviews

Whispering Woods Guest House

James H, JrRating, 5 stars5 months ago
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!!!
Guest favorite
A welcoming entryway features a vibrant yellow door framed by light fixtures, complemented by a decorative bear sculpture on a stone pathway. A large bush and windows add greenery to the red exterior of the house, creating a homey appearance.
Home in Copake
4.92 out of 5 average rating, 65 reviews

Yellow Door House

LaurieRating, 5 stars2 weeks ago
My friend and I really enjoyed our stay at the yellow door house. It really had everything we needed and more as far as kitchen supplies. Kathleen was really responsive when we had a hard time with the TV but she really should have better instructions for that and for the garage door (since we couldn't figure out how to open it to put the garbage out!) We loved the area. It's a little far to a bigger grocery store unless you want to spend a fortune at the general store! We loved Dad's Copake Diner.
Top guest favorite
The exterior of the cottage is framed by lush greenery, with a wooden trellis adorned with vibrant purple flowers. Sunlight filters through the surrounding trees, highlighting the soft colors of the house and creating a tranquil atmosphere.
Home in Lenox
5 out of 5 average rating, 14 reviews

Lenox Cottage

KarenRating, 5 stars1 month ago
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!
Top guest favorite
The exterior of a historic red house is surrounded by lush green grass and trees. A stone path leads to the front entrance, while flowering plants add a touch of color to the landscape. The sky is clear with some clouds, creating a serene outdoor setting.
Home in Old Chatham
4.98 out of 5 average rating, 47 reviews

The Red House

SandyRating, 5 stars1 week 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 favorite
A modern two-story home is surrounded by greenery, featuring large windows that provide ample natural light. A spacious deck extends from the upper floor, and red outdoor chairs are arranged on the lush lawn. The exterior showcases a combination of stone and wood finishes.
Home in Becket
4.96 out of 5 average rating, 26 reviews

New Shaw Pond Skytop Retreat in the Berkshires

NancyRating, 5 stars5 months ago
We stayed here on our way to Stowe to break up our long drive with an 8 and 2 year old. It ended up being a wonderful mini trip that we didn't want to leave. The house exceeded our expectations in terms of quality, cleanliness, and amenities. And the location was excellent - about 10 to 12 min to the nearest grocery store and downtown with restaurants, Edith Wharton's estate about 20 min away, and Great Barrington/Stockbridge were easily accessible for day trips. We plan to come back for skiing, and to take advantage of the lake activities in the summer. The only downside was the busy road, as mentioned in the listing, but the traffic quieted down in the evening and it didn't affect our sleep at night with the bedrooms located in the back of the house (husband is a very light sleeper; we did bring and use sound machines just in case).
Top guest favorite
A warm fire burns within a stone fire pit, with flames flickering against the evening sky. The serene lake reflects the fading light, while a wooden dock is visible in the distance, surrounded by tall reeds and lush greenery.
Home in Lenox
5 out of 5 average rating, 26 reviews

Lakefront Retreat -Private Dock,creek,and Fire pit

LizRating, 5 stars1 month ago
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!
Guest favorite
A red brick cottage is set against a backdrop of lush green grass and trees. The home features a gabled roof and large windows. A small, decorative arbor with climbing plants stands in the foreground, providing an inviting entrance to the property.
Home in Canaan
4.97 out of 5 average rating, 69 reviews

Crossings Cottage

SimonRating, 5 stars1 month ago
Great property with good access from I-90 and close to Albany and the Berkshires. Only downside was the traffic noise and the occasional train (but we do live somewhere super quiet!) but it was not disruptive, even when sitting on the deck. The view from the deck was excellent and it’s a great place just to sit and have your coffee. Property was very clean and had everything you need for a stay. The welcome guide was useful and we tried a few of the local places suggested (all good!). Would definitely stop there again!

Condo rentals with a patio

Guest favorite
A well-lit bedroom features a spacious bed covered in neutral bedding. A wooden dresser and a small nightstand with a lamp are positioned beside the bed. Natural light streams through a round window highlighting the warm wood floors.
Condo 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 favorite
A spacious living area features an arrangement of dark leather seating and a wooden dining table. Natural light streams through sliding glass doors that open to a balcony. A stone fireplace adds character, while decorative plants and artwork enhance the inviting ambiance.
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 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 favorite
Condo in Lenox
4.97 out of 5 average rating, 34 reviews

Spacious 3 bedroom apt in Lenox historic downtown

JamieRating, 5 stars1 week 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 favorite
A cozy bedroom setting features a spacious bed with a patterned coverlet. A television is positioned across from a comfortable seating area with cushions. A writing desk with a lamp is placed near a window adorned with patterned curtains, allowing soft natural light to enter the room.
Private room in Saugerties
4.88 out of 5 average rating, 183 reviews

Hudson Valley Hiker’s Loft-Private Room Queen Bed

KristinRating, 5 stars2 days 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!
A comfortable living room is presented with two sofas adorned with festive cushions. A coffee table is centered on a cozy area rug, while a television sits atop a media console. Large windows framed by dark curtains allow natural light to fill the space.
Condo 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
A spacious light blue deck is shown, furnished with a small table and two white chairs. The surrounding area features greenery and a distant view of rolling hills, providing a serene outdoor space for relaxation.
Condo in Shelburne Falls
4.92 out of 5 average rating, 48 reviews

Flowers & Falls Spot House

TerriRating, 5 stars1 week ago
Always an easy peaceful stay whenever we stay at David’s place. We will be back again
Superhost
A view of a downtown street, featuring a sidewalk lined with chairs and tables outside a café. Red accents can be seen on the café's exterior. Buildings of varying heights line the street, with greenery visible in the background under a cloudy sky.
Condo in Adams
4.76 out of 5 average rating, 41 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”. 😊
A cozy bedroom features a comfortable double bed with dark blue bedding, complemented by two matching pillows. A lamp on a nightstand provides soft lighting, while a window with sheer curtains allows natural light to fill the space.
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 vacation rentals with a patio in Stockbridge

  • Total rentals

    70 properties

  • Nightly prices starting at

    G$16,786 GYD 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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