
Holiday rentals with outdoor seating in Lenox
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Top-rated rentals with outdoor seating in Lenox
Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.
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Popular amenities for outdoor seating rentals in Lenox
House rentals with outdoor seating

Whispering Woods Guest House
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!

Net Zero home with rustic Berkshire charm
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!
Woodstock Historic Artist Estate - The Pond House
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.

The Aviary
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.

Sun-filled, Charming Stockbridge Classic- In Town!
Great location and house. Will definitely recommend to others who wish to stay in the Berkshires! Thanks so much for your flexibility!

Cantabile life in the Berkshires
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.

Granite Ledge, Modern home in a unique setting
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.

Hidden Oasis in the Mountains by Evergreen Home
Beautiful place! Great location and well kept/well maintained house.
Apartment rentals with outdoor seating

In town, newly renovated studio with private deck
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.

Sunny, light filled loft in 1873 Colonial
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.

West Main
Loved this little apartment. It has everything you need and more.

Quiet getaway in the Berkshires
Very nice place would stay again joy was very friendly had no problems with the place at all tyvm again joy

Serene Suite by Gt. Barrington, Hudson, Tanglewood
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.

Beautiful space in the heart of Philmont
Wonderful stay! Beautiful home and so much to do in the area. We had a great time!

King Bed|Wi-Fi|2m Ski Resort
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 :)

Sunny carriage house apartment
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

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!

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

Ski Condo 5 Min from Mt Snow
Lovely home, looked just as described, very responsive/ accommodating host. Stunning Mountain View’s whichever direction you drive. Will definitely be coming back here!

Lovely 1bedrom apartment with screened in porch
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!

Wyndham Bentley Brook
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!!!

3 Story Condo - 5 Minutes to Mount Snow!
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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- Hunter Mountain
- Six Flags New England
- John Boyd Thacher State Park
- Albany Center Gallery
- Jiminy Peak Mountain Resort
- Taconic State Park
- Berkshire East Mountain Resort
- Catamount Mountain Ski Resort
- Zoom Flume
- Windham Mountain
- Kent Falls State Park
- Bash Bish Falls State Park
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- Norman Rockwell Museum
- Mohawk Mountain Ski Area
- Beartown State Forest
- Hartford Golf Club
- Bright Nights at Forest Park
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Hunter Mountain Resort
- Opus 40
- Naumkeag