Smoking-friendly holiday rentals in Pioneer Valley

Find and book unique smoking-friendly rentals on Airbnb

Top-Rated Smoke-Friendly Accommodation in Pioneer Valley

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

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Guest favourite

Apartment in Northampton

4.98 out of 5 average rating, 163 reviews

Skylights, art + design in best downtown location

Elegant spacious sun-drenched 2-bdrm penthouse in gracious 4-family Victorian on tree-lined street in the heart of downtown Northampton. Easy walk to Smith College campus. Skylights; large tiled bathroom with shower, jacuzzi tub, washer/dryer; hardwood floors; renovated kitchen with Italian-tiled floor; open floor plan with ample dining area; living area with large leather couch, handmade rustic wood coffee table, 42" TV, Yamaha digital piano, cathedral ceiling, and glass doors onto a balcony.

12–19 Jun

$611 NZD per night

Guest favourite

Cabin in Lanesborough

4.98 out of 5 average rating, 40 reviews

Glamping in the Berkshires w/ car charging station

Private cabin located in Lanesboro, MA. at the hub of cultural Berkshires, minutes from The Clark Art Institute, Williamstown Theatre and Mass MoCA . Nestled at the base of Mt. Greylock and less than an hour from Barrington Stage, Shakespeare & Co, The Colonial Theatre, Tanglewood, The Norman Rockwell Museum, Jacob's Pillow, The Theatre Barn, Canyon Ranch, Naumkeag and many others. Located close to Ashuwilticock Rail trail, the Appalachian trail and hiking trails on Mt. Greylock Reservation.

17–24 Mar

$817 NZD per night

Guest favourite

Home in Plainfield

4.73 out of 5 average rating, 149 reviews

Sleeps upto 10ppl, Wi-Fi w/ fireplace

Secluded Berkshire house surrounded by 10,000 acres forest is with marked trails & pond that sleeps up to 10 people comfortably. Central air & heat, fireplace, propane BBQ & charcoal BBQ & smoker BBQ, Fibre high-speed WiFi gigabit internet (new in January 2020), Roku streaming device with Netflix & Amazon Prime & hundreds more channels, gazebo, private pond, comfy mattresses/beds, 2 bathrooms, new laundry dryer, 16 foot C shaped couches, indoor garage parking, vegetable gardens, kayaks & more.

7–14 Jan

$551 NZD per night

Guest favourite

Apartment in Coventry

5.0 out of 5 average rating, 51 reviews

Hide Away at Rock Farm UConn Private BnB “5 Star”

Relax with the whole family at this private peaceful “Hide Away” 1000+ sf of space, 600ft off the road in the woods. Well lit, all amenities of home. Enjoy the private deck on sunny mornings. 5 min walk to Bolton Lakes. Fishing, Kayaking & trails. Central to many locations & venues. See our VIP GUEST BOOK for The Get Away on Rock Farm & The Hide Away at Rock Farm. A no-shoe, clean place, comfortable homey feel. 5⭐️ Needing less space? Check out the Get Away https://www.airbnb.com/h/onrockfarm

26 Apr – 3 May

$256 NZD per night

Guest favourite

Home in Chester

4.97 out of 5 average rating, 39 reviews

Halloween Decorated Turn of Century Family Home

At Kenyon's Keep it's Halloween year-round. The home is filled with Halloween decorations and antiques. With a vintage /gothic vibe, it's great for cosplay photos. The house is connected to the owner's Gallery & Studio, expect the first floor to be shared with owner during the day - your evenings will be private. Conveniently located 19.2 miles from MA Turnpike I-90 exit 10 in Lee and 21.7 miles from MA Turnpike I-90 exit 41 in Westfield . Please read full description under THE SPACE

29 May – 5 Jun

$218 NZD per night

Guest favourite

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.

26 Jul – 2 Aug

$283 NZD per night

Guest favourite

Treehouse in Guilford

4.99 out of 5 average rating, 84 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.

3–10 Nov

$232 NZD per night

Guest favourite

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.

9–16 Jul

$242 NZD per night

Superhost

Home in Otis

4.85 out of 5 average rating, 26 reviews

Berkshire Lakefront Lighthouse Getaway

Escape to your own slice of paradise in our 450 Sq. Ft breathtaking Lighthouse rental on East Otis reservoir! This stunning property boasts a multi-level 800 square foot deck with jaw-dropping views of the shimmering Lake below making it the perfect place to unwind and soak up the natural beauty of Massachusetts. For water enthusiasts, the lighthouse rental also includes a 500 ft shared dock, providing easy access to the lake for swimming, fishing, kayaking and more.

27 May – 3 Jun

$630 NZD per night

Guest favourite

Home in Shelburne Falls

4.97 out of 5 average rating, 93 reviews

Modern Shelburne house on 37 private acres.

Modern 4 bedroom home on a private mountain top with 37 acres of hiking, streams, and wildlife. The amenities are contemporary and comfortable. The views and privacy are stunning. Close to Shelburne Falls, Deerfield, Northampton and Berkshires East. Enjoy apple orchards, antiques, petting zoo, farm stands, swimming and so much more. This is a perfect family retreat offering everything you need to feel at home...while it feels a million miles away.

23–30 Oct

$950 NZD per night

Guest favourite

Cabin in Andover

5.0 out of 5 average rating, 54 reviews

Cozy cabin 7-Acres & Pond!

A natural getaway for couples, nomad workers, families, pets, bikers, hikers, kids.. you'll love our 750 sf cabin with pond on huge yard. Full kitchen, large balcony-deck, fire pit, pond, and parking for 4 cars. "East Coast Greenway" is just steps from our driveway... walk 1/2 mile to a lovely meandering waterfall. Just 15-min to Manchester, Vernon, UCONN; 30-min to Hartford, casinos, airports. (Pls declare pets under "Guests".)

12–19 Sep

$299 NZD per night

Guest favourite

Cabin in Pelham

4.94 out of 5 average rating, 48 reviews

Cabin Camp Retreat

Nourish your soul and unplug (limited electricity) in this back to nature retreat right on the edge of town. Experience the rare birds that migrate to this special place. Sun bath in the hammock or hike to the views of Mount Orient or the babbling brooks of Buffam Falls. With an outdoor kitchen, fire pit, fresh spring, mountain views, expansive night sky, and composting outhouse, the cabin retreat could be just what you need.

18–25 Aug

$245 NZD per night