Smoking friendly vacation rentals in Western Massachusetts

Find and book unique smoking friendly rentals on Airbnb

Top-rated smoking friendly rentals in Western Massachusetts

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

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Guest favorite

Guesthouse in Woodstock

5 out of 5 average rating, 344 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

Rental unit in Northampton

4.98 out of 5 average rating, 288 reviews

Sunny Inspirit Apartment in best downtown location

Two blocks from Main St & steps from Smith College, in the heart of vibrant downtown, this sun-flooded 2br apt/terrace with original 1890s wood floors is in the home of the family behind Northampton's iconic Inspirit Crystals shop. Your 2 south-facing BRs (1 w/sitting area) are drenched in sunlight. A fully equipped eat-in kitchen opens onto a small private terrace with café seating for 2 overlooking tree-shaded Trumbull Rd. Shared outdoor pool, garden w swing, play gym & sandbox for kids' use.

Guest favorite

Tiny home in Cambridge

4.94 out of 5 average rating, 201 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.

Superhost

Tent in Bloomingburg

4.87 out of 5 average rating, 439 reviews

Δ Heated Glamping Tent! -Scenic Hiking Paradise!

☮ Your Campsite is atop the Shawangunk Mountain Ridge! -BEAUTIFUL SCENIC Official Marked Trails within a 1/8 mile! See Pics! -PROPANE HEATER -Awake to chirping birds with Rays of Morning Sun and shadows Dancing on your Tent -Access to Private Bathroom & Well Equipped Kitchenette -OUTDOOR & INDOOR SHOWER -Clean Bedding and Towels Provided -Make Breakfast on Campfire or GAS GRILL -WIFI & Electricity in Tent! -Adjacent to 2 State Forests with 1600+ Acres! -CANOPY WOODS YOU CAN WALK AROUND IN

Guest favorite

Barn in Canterbury

4.95 out of 5 average rating, 244 reviews

The Barn

Welcome to The BARN! You can expect to feel tucked away in the trees in this cozy, rustic, yet chic space. Thoughtful lighting, fine linens and furnishings with a spacious and private deck off the back to sit and enjoy nature or entertain. Miles of wooded forest is this location; if you’re looking to escape the city or a busy life, this is the perfect place to explore, relax and revive. At the main house (across the way), there are horses, barn kitties, cattle dogs and other friendly animals.

Guest favorite

Condo in Windham

4.88 out of 5 average rating, 165 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

Tiny home in Norwich

4.99 out of 5 average rating, 813 reviews

Water Forest Retreat -Octagon

Water Forest retreat is a very private 122ft.² electrified and heated cedar octagon next to a brook on 56 acres of forest with a pond, waterfall, marsh and hiking trails. Cozy up in this quiet comfortable space while listening to Goldmine brook while you sleep. Fire pit, heated outhouse with composting toilet, outdoor dining area, brook, pond and trail head are just steps away. We also have a TREE HOUSE and HIKER’S HAVEN house by the brook. Please click on our profile picture to read more.

Guest favorite

Rental unit in Stafford

4.94 out of 5 average rating, 144 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

Rental unit in Coxsackie

4.97 out of 5 average rating, 137 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, 137 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, 347 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, 119 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.