Smoking friendly vacation rentals in The Berkshires

Find and book unique smoking friendly rentals on Airbnb

Top-rated smoking friendly rentals in The Berkshires

Guests agree: these smoking friendly rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Cabin in Livingston Manor

4.97 out of 5 average rating, 276 reviews

Experience The Zen House

Enjoy your own private indoor HD movie theater with 5.1 Bose Surround Sound and leather recliner seats, a spa with a cold plunge pool and sauna, and a hot tub to reach the maximum level of relaxation. Play a game of ping pong, enjoy the fireplace outside and inside along with 5 acres! Here are some of the key amenities: -Hot Tub (2021) -Sauna & Cold Plunge Pool -Private 12 Person Movie Theater (you can plug in your device) -Table Tennis/Ping Pong and much more! Check us out on ig: @zenhouseny

Guest favorite

Guesthouse in Woodstock

5 out of 5 average rating, 330 reviews

Steps toTown/Bus Pet Ok/No Extra Fees! &Five Star

PRIVATE Modern/Rustic Apt WALK TO ALL 5 * Rating "premiere" NO EXTRA CHARGES! 1000 sq ft Pet Friendly n/c Park Master King Suite &I can put up 2cots /crib Full Kitchen Cathedral Living Room w/Mountainview. 1&1/2 Bath Deck for Outside Dining w/Mountainview WOOD FIREPLACE on deck Wi-Fi Wash/Dryer Gas BBQ Steps to CTR of Town Green & NYC Bus-stop, THE COLONY, Yum Yum, Goodnight , Garden Cafe, Silvias, Bread Alone, Mud Club, Station Bar, shops . Cemetery's Bubbling Stream, PrivatePlayground

Guest favorite

Tiny home in Cambridge

4.95 out of 5 average rating, 194 reviews

Runamuk Farm camp with a view!

Picturesque location on farmland with views of the mountains. We are a micro farm. Wake up and watch the sunrise and go for a short hike on the property, and get to know the animals. We are located 35 minutes from Saratoga Springs and Lake George, NY and 45 minutes from Dorset and Manchester, VT. Hike the Adirondack or Green Mountains, paddle the streams or go to a nearby small city for a play, a festival, or a concert. There is a long list of things to do and see within an hour of our camp.

Guest favorite

Tiny home in Norwich

4.99 out of 5 average rating, 559 reviews

Water Forest Retreat-Hikers Haven

Water Forest Retreat Hiker's Haven is a very private semi off grid electrified and heated tiny house just steps away from a brook nestled on 56 acres of lush forest. Enjoy the water views inside from the many windows or out on the deck or firepit area. There are 2 1/2 miles of hiking trails with a pond, marsh and small waterfall. Come here to hike, fish, decompress and rejuvenate in this magical woodland! We also have an Octagon and Treehouse. Please click on our profile picture to read more.

Guest favorite

Condo in Windham

4.89 out of 5 average rating, 158 reviews

Cozy Mountain hideaway Windham, Hunter

Spacious 1BR condo for a max. of 4 guests , sleeps 2 in separate bedroom , additional 2 on an inflatable airbed . Balcony with mountain view ,2 tennis courts ,outdoor pool . Awesome location . Windham and Hunter within reach .Get close to nature in the nearby hiking trails, Windham Path, Kaaterskill Falls. Kayaking on North-South Lake or ziplining in Hunter,skiing ,snowboarding ,golfing and mountain biking . Leave your worries at home and come to relax.Enjoy many dining options in town.

Guest favorite

Rental unit in Stafford

4.94 out of 5 average rating, 142 reviews

Modern Industrial Apartment with rooftop access

Modern industrial apartment with roof top access located in an old Mill Building/Artist Community. We are located perfectly in the middle between Boston and NYC, 15 minutes to UConn, 20 minutes to the Brimfield Antique show and 40 minutes to the new MGM Casino in Springfield, MA. Our town offers many restaurants, boutique stores and parks all within walking distance along with Art and Music events.There is a Yoga studio, Recording Studio, Dance Studio and Vintage Shop on our premises.

Guest favorite

Guesthouse in Schoharie

4.9 out of 5 average rating, 119 reviews

Two Bedroom Country Getaway.

Welcome to our 2 bedroom, 1 bathroom country getaway. We are minutes from the historic village of Schoharie and 45 minutes from the Capital Region and Cooperstown. We offer scenic views, lawn access around the air bnb, outside seating and parking ( up to two cars). Our air bnb comes fully stocked with towels, linens, toiletries, hair dryer, kitchenware, 55’ smart TV, pack n play and portable high chair. There are 13 steps to enter air bnb. Must be able to climb without assistance.

Guest favorite

Rental unit in Coxsackie

4.97 out of 5 average rating, 130 reviews

Susie's Climax Creations

Susie's Climax Creations Farm is where you can experience a stay on a farm. The charming farm house is roughly 200 years old, located 2.5 hours from NYC, 25 minutes from the Hudson train station. If you want to stay somewhere safe from Covid-19 exposure this is the place! Susie's Climax Creations is on a quiet dead end street. The apartment has a private entrance and completely self contained. If you would like to see more of the farm animals check out my site located at Kliese140.

Guest favorite

Treehouse in Guilford

4.99 out of 5 average rating, 125 reviews

Cozy tent in the trees on organic flower farm

Tuck yourself into a mature oak forest on the field’s edge of our flower farm, Tapalou Guilds. All-weather canvas tent is pitched with a comfy king mattress inside. Three elevated decks with chairs and a hammock give you options for relaxing and steeping in the forest vibe. Fully equipped outdoor kitchen with propane gas range. We provide potable water from our well. Outdoor shower with on-demand hot water. Simple outhouse with sawdust composting system is clean and convenient.

Guest favorite

Cabin in Kerhonkson

5 out of 5 average rating, 337 reviews

The Metsämökki - A Finnish Cabin in the Woods

The Metsämökki is a small Finnish cabin in the foothills of the Catskill Mountains. Originally a sauna that was shipped here from Finland. We renovated it to a tiny house that offers complete privacy. Enjoy the babbling brook while sitting on the deck and taking in the surrounding nature. We're not offering high-tech or glamour but this cabin is a beautiful retreat from the busy city. **Check out our new midweek discounted rates and enjoy a little extra time for a great price!!

Guest favorite

Cabin in Bearsville

4.99 out of 5 average rating, 116 reviews

Watson Woods Cabin

Far from noise and distraction. Surrounded by wilderness yet only four miles to the center of Woodstock. The house sits on 5 acres of private land in a wooded hamlet surrounded by other homes. Situated on top of a small hill with our other property - the Studio - down below. Nearby stunning Cooper Lake and Mink Hollow hiking trail. Rustic architecture meets mid-century design. An indoor napping hammock under a Nelson light…Nooks with views for reading, writing and streaming.

Guest favorite

Rental unit in East Haddam

4.9 out of 5 average rating, 142 reviews

Penny Corner Airbnb

My place is located up the hill from Good Speed Opera House. The Opera House is on the same side of the river as my place. The folklore is that vacationers used to pay a penny to have their belongings transported by ox and wagon from the port at the river to this corner. A two family home built in 1884. The space is a ground level 1 bedroom apartment with private entrance. There is no TV in the unit, WIFI is available for your devices.