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Smoking friendly vacation rentals in Pioneer Valley

Find and book unique smoking friendly rentals on Airbnb

Top-rated smoking friendly rentals in Pioneer Valley

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

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Guest favorite
A living area features a spacious blue sofa with ample cushions, complemented by a wooden coffee table. Large sliding glass doors provide access to a balcony, framed by light curtains that enhance natural light. Two windows on the side allow additional sunlight to fill the room.
Apartment in Northampton
4.91 out of 5 average rating, 223 reviews

1880s balconied luxury pad, best downtown location

Bright, newly renovated, luxuriously furnished, tree-lined flat a few steps from Northampton's vibrant downtown. Sliding glass doors open to a lovely balcony overlooking trees and roofs. Open floor plan, eat-in butcher-block kitchen, dishwasher, living room with movie projector, home theater system, queen pullout sofa. Spacious queen bedroom with 42" HDTV, private study nook. Access to yard areas with outdoor dining table, heated 36-ft pool, play gym. Basement washer/dryer. Off-street parking.

Top guest favorite
A spacious living area is characterized by high beamed ceilings and large windows that allow natural light. Furnishings include a round dining table surrounded by six chairs and a comfortable seating arrangement, featuring a decorative rug. A large television is positioned on a wooden stand.
Apartment in Coventry
5 out of 5 average rating, 129 reviews

HideAway Storrs Coventry RockFarm BnB Breakfast A+

Enjoy your visit at “The Hide Away” on RockFarm with Super Hosts Jon & Jeri. The family friendly 1000+ sf 2 bdrm apt 600ft wooded, well lit, all amenities of home. WIFI 500 Mbps, TV ROKU. Enjoy the private deck, full kitchen, laundry, lvg rm & Dining. Drive UConn 15 min, Bolton Lakes 2 min fishing & hiking trails. View our VIP GUEST BOOK for activities and good eats! A private no-shoe, clean, comfy home. 5⭐️ 100% loved! 32 yrs no crime! See the Get Away too. https://www.airbnb.com/h/onrockfarm

Guest favorite
A charming house is surrounded by lush greenery and colorful flowerbeds. A gravel driveway leads up to the home, with a gazebo visible in the background. Comfortable seating areas on the porch invite relaxation amidst the tranquil landscape.
Home in Plainfield
4.74 out of 5 average rating, 167 reviews

Fall foliage surrounded by 10,000 acres forest

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.

Guest favorite
A cozy living space features a sectional sofa and a wooden entertainment unit with a large TV. In the background, a kitchen area is visible, equipped with wooden cabinets and essential appliances. A round dining table with chairs is seen, illuminated by soft overhead lighting.
Apartment in Wilmington
4.9 out of 5 average rating, 135 reviews

Walk To Wilmington Village

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. Washer/dryer Smart TV with premium streaming services The front porch, side porch, and the yard on that side is all private and for you to enjoy. Please note, I live next door, and I have a dog.

Top guest favorite
The rustic cabin is illuminated by bright outdoor lights, highlighting its unique architecture. The deck is visible, surrounded by a grassy area, while a flag stands at one end. The warm glow creates a welcoming ambiance against the night sky.
Cabin in Lanesborough
4.98 out of 5 average rating, 52 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, attractions include 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.

Top guest favorite
An elevated wooden deck is surrounded by trees, featuring a canvas tent. Two red folding chairs are positioned nearby, alongside a hammock suspended between two posts. Sunlight streams through the leaves, highlighting the natural setting.
Treehouse in Guilford
4.99 out of 5 average rating, 178 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
A charming cabin with a sloped roof is surrounded by autumn foliage. Large windows allow natural light to filter in, and a well-maintained path leads to the entrance. Steps ascend to a balcony, enhancing accessibility and outdoor enjoyment.
Cabin in Andover
4.94 out of 5 average rating, 94 reviews

Cozy cabin 7-Acres & Pond!

A cozy getaway for couples, nomad workers, families, pets, bikers, hikers... all love our 750 sf cabin with pond and huge yard. Full kitchen, large balcony-deck, fire pit, pond, and parking for 4 cars. The "Hop River Trail" is just steps from our driveway. Walk a 1/2 mile to a lovely meandering waterfall, or walk for miles if you love a good hike. Just 15-min drive to Manchester, Vernon, UCONN Storrs; only 30-min to Hartford, casinos, airports. (Pls declare pets under "Guests".)

Superhost
A spacious yard adorned with greenery features a small dog wearing a bright vest. In the background, the two-story house displays a deck with stairs leading to the ground. Various plants are visible in garden beds, with seating options indicated by a couple of patio chairs.
Farm stay in Hampton
4.83 out of 5 average rating, 18 reviews

House with Yard - Pets Welcome!

Your dog(s) will be so happy! The yard is 13.66 acres to play and explore! I bought this property in March 2022 when I returned from Europe and am turning it in to a hobby farm in my free time. Rather than leave the upstairs unfurnished, I bought all new beds and mattresses with basic furniture, so this beautiful space can be available to you and your pets to enjoy as well. The two floors have private entrances. You have the entire top floor without other guests or me.

Top guest favorite
A view of a modern home surrounded by vibrant autumn foliage, seen from a tranquil pond. The lush greenery and colorful leaves frame the property, creating a serene outdoor setting with a small animal by the water's edge.
Home in Ashfield
4.96 out of 5 average rating, 70 reviews

True Shangri-la, Country Retreat

Modern comforts in this gorgeous, spacious home on 50 acres with a view of the Vermont foothills. Enjoy the pond, fire pit, streams, gardens, deck and access to the sweet town of Ashfield - be out in the woods without being in the middle of nowhere! Fiber Optic high speed internet is wired so you can reliably work and relax. Mass Certificate #C-12336793-003 This listing does require a signed rental agreement (sorry for the formality but my insurance company insists!)

Guest favorite
The lighthouse rental is framed by lush greenery, featuring a multi-level design. A deck extends from the structure, providing direct access to the outdoor area. Views of the serene lake are visible in the background, offering a natural and calming setting.
Home in Otis
4.91 out of 5 average rating, 69 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.

Top guest favorite
Home in Shelburne Falls
4.97 out of 5 average rating, 103 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.

Top guest favorite
A clear, inviting pool is surrounded by lush greenery and mature trees, providing a serene and private atmosphere. The pool features a gently curving shape and is bordered by textured stone paving, with sunlight reflecting off the water's surface.
Apartment in Holyoke
4.8 out of 5 average rating, 266 reviews

NE Historical Mansion-pets and pet lovers welcome

Enjoy seamless check-in and a private 1,000 sq ft space on the third floor of our historic Victorian home. Includes 2 bedrooms, bathroom, open hallway, and a combined living/dining/kitchenette area (no sink). Pet-friendly, updated, and comfortable year-round. Accessed via the back staircase; only the entry/hallway is shared. 3rd and Top floor is strictly for guests only. Just 5 min to I-91 and Pike, 15 min to Northampton 15 min to Big E.

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