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

Guesthouse in Woodstock

5.0 out of 5 average rating, 301 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

Mar 28 – Apr 4

G$50,714 GYD per night

Guest favorite

Tiny home in Cambridge

4.95 out of 5 average rating, 168 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.

Jun 12 – 19

G$18,288 GYD per night

Guest favorite

Apartment in Amherst

4.92 out of 5 average rating, 179 reviews

Historic 1840 beauty in best downtown location

Newly restored 2nd-floor apartment in 175-year-old home 2 blocks from Amherst Cinema & steps to everything this vibrant downtown has to offer. Walking distance to Amherst College and UMass. This home retains the character of days gone by, yet sparkles with new wood floors, modern bathroom & new appliances. Original wood-paneled entry hallway & exposed beams throughout. Antique furnishings, historic wall decor, and a sunny kitchen with built-in reclaimed wood bar. Small balcony w seating for 2.

May 21 – 28

G$51,749 GYD per night

Guest favorite

Condo in Windham

4.89 out of 5 average rating, 133 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.

Jul 27 – Aug 3

G$22,934 GYD per night

Guest favorite

Apartment in Stafford

4.93 out of 5 average rating, 123 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.

Mar 10 – 17

G$31,267 GYD per night

Guest favorite

Apartment in Coxsackie

4.96 out of 5 average rating, 114 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.

Jan 21 – 28

G$24,306 GYD per night

Guest favorite

Cabin in Kerhonkson

5.0 out of 5 average rating, 308 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!!

Apr 1 – 8

G$32,354 GYD per night

Guest favorite

Cabin in Bearsville

4.99 out of 5 average rating, 114 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.

May 13 – 20

G$83,266 GYD per night

Superhost

Home in Saugerties

4.93 out of 5 average rating, 338 reviews

Catskills Oasis | Hot Tub, Fire Pit, Fenced Yard

The Hartwood House is the perfect upstate getaway. Located in beautiful West Saugerties, this 2 bedroom/1 bath house is a great place to unwind and relax. Secluded and quiet, a centerpoint to explore the Catskills. Just minutes to all the Woodstock/Saugerties destinations, HITS, Hunter Mountain, and more. This is a private oasis in the heart of the Catskills. Features include a hot tub, fully fenced yard, fire pit, BBQ, and more to make experience one you'll never forget!

Sep 24 – Oct 1

G$88,518 GYD per night

Guest favorite

Apartment in Wilmington

4.92 out of 5 average rating, 108 reviews

Walk To Wilmington Village (Reduced Spring Rate)

This charming apartment is on a quiet side road overlooking historic downtown Wilmington, Vermont. Hear the church bells nearby while enjoying a relaxing evening on the deck. Take a stroll downtown and visit restaurants, shops, bars, and giftshops. Easy access to Moover, free bus to Mount Snow. Brand new washer/dryer Smart TV with a variety of premium streaming services The entire covered porch, side porch, and the yard on that side is all private and for you to enjoy.

Jul 9 – 16

G$24,920 GYD per night

Guest favorite

Cabin in Accord

4.86 out of 5 average rating, 251 reviews

Timberframe

The Timberframe is a handmade seasonal building with a full size memory foam bed on the same property as the main house. It was my Old Painting Studio. There is a full bathroom in the main house on the first floor just for guests. Due to Covid-19. there is also porty-potty 40 feet from the Timberframe, outdoor hand washing sink and a sun shower. Our Boodle Hole Beach is 4 min car ride away..beautiful refreshing stream, 13 acres..Details in the booklet when you arrive.

Jan 27 – Feb 3

G$25,022 GYD per night

Guest favorite

Apartment in East Haddam

4.89 out of 5 average rating, 106 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.

Feb 16 – 23

G$21,411 GYD per night