Holiday rentals with outdoor seating in Lenox

Find and book unique Holiday Houses with Outdoor Seating on Airbnb

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Popular amenities for Lenox outdoor seating rentals

Holiday 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 Lee
4.87 out of 5 average rating, 46 reviews

Spacious & Family-Ready Home w/ Fenced Yard in Lee

MauraRating, 5 stars1 month ago
We had a great stay! Vinicius’s home was clean, conveniently located to explore the Berkshires and easily accommodated our party of four, plus a dog. The fenced-in yard came in very handy with the latter!
Guest favourite
Home in Richmond
4.94 out of 5 average rating, 18 reviews

Sunshine Cottage

EdRating, 5 stars8 months ago
We only stayed one evening but found the living space to be perfectly laid out and spotless. The kitchen is fully stocked with about every utensil and appliance you can think of. We especially enjoyed the fresh eggs, treats, and flowers that welcomed us! The living room was especially comfortable. The unit is attached to the rear of the main house but it’s kept totally private. There aren’t many places to eat in Richmond — after all, it is pretty rural— but Stockbridge and Lennox offer many dining options.
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 Becket
4.88 out of 5 average rating, 345 reviews

Real Estate:Therapy - Lake, Laundry, Love it

DavidRating, 5 stars2 weeks ago
We had a good time, and the lake was very nice. Thank you!
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 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
Apartment in Shelburne Falls
4.98 out of 5 average rating, 561 reviews

In town, newly renovated studio with private deck

JoelleRating, 5 stars3 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
Apartment 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.
Superhost
Apartment 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
Apartment 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
Apartment 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
Apartment 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
Apartment 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 :)
Top Guest favourite
Apartment in North Adams
4.97 out of 5 average rating, 560 reviews

Steps to MoCA: 2bd + SAUNA!

RyanRating, 5 stars1 week ago
Matti was a friendly and thoughtful host who made us feel welcome from the start. He reached out ahead of time with helpful info and made check-in easy. The place matched the listing perfectly—if anything, it was a bit nicer than expected—and was a great value for the area. Both bedrooms were comfortable and had blackout shades. The shower had great water pressure and was a nice way to start the day. Everything was clean and functional, and we enjoyed the custom furniture pieces. The location was another plus- it was easy to get around on foot. We walked to dinner, grabbed coffee in the morning, and picked up a few things from the grocery store—all without needing to drive. Overall, this was a great place to stay with everything we needed. I’d definitely recommend it for anyone looking for a well-priced, comfortable option in the area.

Condo rentals with outdoor seating

Guest favourite
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 favourite
Condo 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
Condo in Dover
4.83 out of 5 average rating, 108 reviews

Mount Snow Ski Chalet

BarryRating, 5 stars3 months ago
Great place to stay. There are no Ubers the week we stayed there and we should have rented a car. But the place was great.
Guest favourite
Condo 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!
Top Guest favourite
Condo in Dover
4.99 out of 5 average rating, 120 reviews

Summer Dream! The Handle Lodge at Snowtree Condos

MarkRating, 5 stars3 months ago
Our family enjoyed our stay at Rafael's condo. The space was very clean and comfy, and exactly matched the description and photos posted here. The fireplace was a great draw, too. If you're planning on skiing at Mt. Snow, the Moover shuttle bus stop is located right outside of this building, which made for a very convenient and quick way to get to Mt. Snow for my family of 4. We would certainly stay here again in the future.
Guest favourite
Condo in Dover
4.95 out of 5 average rating, 61 reviews

Condo w/ great amenities 4-seasons! Ski in Ski out

BrianRating, 5 stars4 days ago
Christine was a great host. The condo was as described. The place was clean and well organized, very cute and cozy. Christine was very responsive and helpful. I will definitely stay here again.
Top Guest favourite
Condo 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
Condo 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!!!

Quick stats about holiday rentals with outdoor seating in Lenox

  • Total rentals

    110 properties

  • Nightly prices starting at

    $100 NZD 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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