Holiday rentals with outdoor seating in Lenox

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Popular amenities for outdoor seating rentals in Lenox

House rentals with outdoor seating

Guest favourite
Home in Pittsfield
4.95 out of 5 average rating, 21 reviews

Whispering Woods Guest House

JanetteRating, 5 stars2 months ago
Taylor was an amazing host! Her home was super comfortable! We would absolutely stay again if we are in the area! Thank you for the amazing stay!
Guest favourite
Home in Pittsfield
4.93 out of 5 average rating, 103 reviews

Net Zero home with rustic Berkshire charm

BeccaRating, 5 stars1 week ago
We had a great stay during our work trip to the Berkshires! Our toddler loved playing in the enclosed front porch and fenced in yard, and the crib and baby gates were such nice amenities for my peace of mind. Everything was clean and comfortable and we appreciated that Chamaio reached out to let us know when the home was ready for us, and gave suggestions on local spots nearby. We would absolutely stay here again if (hopefully when!) we are back in the area!
Guest favourite
Home in Woodstock
4.94 out of 5 average rating, 338 reviews

Woodstock Historic Artist Estate - The Pond House

CodyRating, 5 stars1 month ago
No notes, incredible escape even in the pouring rain. The ambience, even down to the little things like walking through the door to classical music, was truly top notch.
Guest favourite
Home in Lenox
4.96 out of 5 average rating, 26 reviews

The Aviary

SaraRating, 5 stars3 weeks ago
The Aviary was beautiful, well stocked and had enough dishes, glasses, and towels to allow all 8 of us to relax comfortably in the house. The house had many seating areas and a table big enough for all of us to eat together. The bathrooms were large and had a lot of space. All the bedrooms were well suited and we were able to sleep comfortably. Unfortunately, the weather was not cooperative but the backyard was inviting and looked like a lovely place to sit and read peacefully. Jacqueline responded quickly to all our questions and check in and out was easy to follow. We all immensely enjoyed our stay and would highly recommend The Aviary to anyone looking for a place with lots of space and close to Lenox.
Top guest favourite
Home in Stockbridge
4.95 out of 5 average rating, 132 reviews

Sun-filled, Charming Stockbridge Classic- In Town!

MichaelRating, 5 stars1 week ago
Great location and house. Will definitely recommend to others who wish to stay in the Berkshires! Thanks so much for your flexibility!
Top guest favourite
Home in Pittsfield
4.95 out of 5 average rating, 174 reviews

Cantabile life in the Berkshires

BillRating, 5 stars1 week ago
Jia place was great. Very spacious and plenty of things to do. It was very clean. The entire process was super simple. We enjoyed it quite a bit.
Top guest favourite
Home in Great Barrington
4.99 out of 5 average rating, 122 reviews

Granite Ledge, Modern home in a unique setting

MichaelRating, 5 stars1 week ago
Had a wonderful time at Granite ledge. Absolutely beautiful backyard. Very peaceful and comfortable. The bed was very comfortable and we slept like babies. Highly recommend and would definitely stay here again.
Guest favourite
Home in Pittsfield
4.98 out of 5 average rating, 125 reviews

Hidden Oasis in the Mountains by Evergreen Home

MattRating, 5 stars2 months ago
Beautiful place! Great location and well kept/well maintained house.

Apartment rentals with outdoor seating

Top guest favourite
Flat in Shelburne Falls
4.98 out of 5 average rating, 561 reviews

In town, newly renovated studio with private deck

JoelleRating, 5 stars2 days ago
Our experience at Carrie's studio apartment was just what we needed after a busy day attending to a family project. The apartment is spacious and nicely appointed with a comfortable bed, couches and lounging chair. The kitchen is well-equipped and the bathroom neat and clean. Although we didn't have much time to enjoy it, a small outside porch overlooking a lower garden and an expanse of a neighbor's green lawn was an added perk. The apartment is a short walk into the village of Shelburne Falls with its diverse shops, many eateries, pharmacy (good spot for an ice cream soda), small grocery store (an organic oriented store is just across the bridge), bookstore, and very nice wine store (near the Pot Holes). Don't miss Gypsy Apple, a culinary treat for a special occasion (check for the evenings open as they are limited). Our respite at Carrie's was peacefully quiet and restorative. I have no reservations about recommending Carrie's lodging.
Guest favourite
Flat in Plainfield
4.97 out of 5 average rating, 271 reviews

Sunny, light filled loft in 1873 Colonial

DouglasRating, 5 stars2 weeks ago
Peter and the apartment were great! Peter was super responsive, friendly, and had nice touches like homemade granola with milk and coffee provided. After my original AirBNB fell through at check-in at 6pm, I was relieved (and saved) by Peter’s responsiveness.
Top guest favourite
Flat in Canaan
4.99 out of 5 average rating, 144 reviews

West Main

AlexisRating, 5 stars2 weeks ago
Loved this little apartment. It has everything you need and more.
Superhost
Flat in Chester
4.77 out of 5 average rating, 202 reviews

Quiet getaway in the Berkshires

GailRating, 5 stars1 month ago
Very nice place would stay again joy was very friendly had no problems with the place at all tyvm again joy
Top guest favourite
Flat in Hillsdale
4.99 out of 5 average rating, 208 reviews

Serene Suite by Gt. Barrington, Hudson, Tanglewood

EuginaRating, 5 stars1 week ago
We booked last minute to stay for a night to attend an event nearby. While our stay was brief, it was super clean, comfortable, and just what we needed. Everything smelled fresh, and Kelly’s recommendations were helpful too.
Superhost
Flat in Philmont
4.9 out of 5 average rating, 118 reviews

Beautiful space in the heart of Philmont

JessicaRating, 5 stars8 months ago
Wonderful stay! Beautiful home and so much to do in the area. We had a great time!
Guest favourite
Flat in Great Barrington
4.9 out of 5 average rating, 129 reviews

King Bed|Wi-Fi|2m Ski Resort

JackiRating, 5 stars2 weeks ago
My new go-to place in the berkshires! I love the berkshires for hiking , my favorite spa (mend), and all the cute shops/food outings! This spot was perfect - it's well-decorated, the bathroom is nice, and the location is GREAT! Loved the back patio for morning coffee. Washer/dryer was fast. Host is very responsive and helpful. Looking forward to my next stay & would love to bring my dog next time :)
Top guest favourite
Flat in Plainfield
4.95 out of 5 average rating, 271 reviews

Sunny carriage house apartment

EllieRating, 5 stars2 weeks ago
We had a great time at this lovely spot! Erin was a very kind and responsive host, and the apartment was just as described :)

Apartment rentals with outdoor seating

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 stars2 months 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!
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
Guest favourite
Apartment in Dover
4.9 out of 5 average rating, 52 reviews

Ski Condo 5 Min from Mt Snow

JadeRating, 5 stars1 month ago
Lovely home, looked just as described, very responsive/ accommodating host. Stunning Mountain View’s whichever direction you drive. Will definitely be coming back here!
Top guest favourite
Apartment in Northampton
4.97 out of 5 average rating, 63 reviews

Lovely 1bedrom apartment with screened in porch

LauraRating, 5 stars1 month ago
Beautiful and very clean space! We had the most wonderful long weekend at Goran's apartment. He was so responsive and super friendly... cannot recommend enough. We will be back!
Superhost
Apartment in Hancock
5 out of 5 average rating, 4 reviews

Wyndham Bentley Brook

Ashley And NathanielRating, 5 stars16 months ago
We had a wonderful time staying at Paul’s place! We had easy access to the mountain for skiing. It was wonderful to have a ski locked to store our stuff outside of the room. In addition to the wonderful accommodation our kids loved the indoor/outdoor pool after a long day on the slopes. Highly recommend Paul and his accommodation!!!
Top guest favourite
Apartment in Dover
4.92 out of 5 average rating, 123 reviews

3 Story Condo - 5 Minutes to Mount Snow!

AlyssaRating, 5 stars2 weeks ago
It was such an easy check in and check out process. He let us check in an hour early since we arrived earlier. Place is spacious and exactly as described. Highly recommend!

Quick stats about holiday rentals with outdoor seating in Lenox

  • Total rentals

    110 properties

  • Nightly prices starting at

    ₹5,180 before taxes and fees

  • Total number of reviews

    4.9K reviews

  • Family-friendly rentals

    70 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with a pool

    10 properties have a pool

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