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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Superhost

Apartment in Northampton

4.88 out of 5 average rating, 136 reviews

Luxury w sunny balcony in 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.

Jul 2 – 9

€ 207 per night

Guest favorite

Barn in Kent

4.89 out of 5 average rating, 66 reviews

Country Guest Cottage/Barn

Enjoy nature in the guest cottage/barn on our property in bucolic Litchfield County. King bed in the sleeping loft and queen bed in the room. Air mattress available. Nestled in the Litchfield Hills three miles from Lake Waramaug and close to the quaint shops, restaurants, galleries and cultural scene in Kent, Bantam, Litchfield, Washington, New Preston and Cornwall, among others. Hike beautiful Kent Falls and explore the many hiking trails and ponds, lakes and rivers. Newly upgraded with Wi-Fi!

Feb 14 – 21

€ 246 per night

Guest favorite

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

Apr 22 – 29

€ 144 per night

Guest favorite

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

Jun 17 – 24

€ 123 per night

Guest favorite

Home in Morris

4.91 out of 5 average rating, 64 reviews

Luxury Compound, Pool, Gym, Tree House, Game Barn

Serene, elegantly appointed historic 19th century farmhouse and compound that has been fully modernized and set on the edge of a 50 acre protected forest that borders spring fed Bantam Lake. Located in the rolling hills of Litchfield County this surprisingly expansive home has been updated with every amenity: pool, hot tub, gym, chef’s kitchen, primary suite with fireplace and soaking tub, pool house guest apartment, gas fireplace in living room, and a magical treehouse in the 3 acre yard

May 7 – 14

€ 538 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.

Jun 24 – Jul 1

€ 149 per night

Guest favorite

Treehouse in Guilford

4.99 out of 5 average rating, 82 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.

Oct 5 – 12

€ 131 per night

Guest favorite

Apartment in Wilmington

4.92 out of 5 average rating, 107 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.

May 27 – Jun 3

€ 112 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.

Jan 19 – 26

€ 354 per night

Guest favorite

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.

Jan 22 – 29

€ 533 per night

Guest favorite

Home in Glastonbury

4.8 out of 5 average rating, 49 reviews

Idyllic Ranch, Centrally Located

You deserve an upgrade without the added price. Centrally located, newly remodeled, fully furnished, and nobody on the premises to bother you. Renovated in 2020, this home was my primary residence for 4 years. I love it so much, I decided to lease it instead of selling. Full kitchen, two-full bathrooms, ample parking, over a half acre of land, and a premium central location. Whether you're alone or with 5 friends, this is the place you want to be

Apr 15 – 22

€ 199 per night

Guest favorite

Cabin in Andover

5.0 out of 5 average rating, 53 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".)

Aug 31 – Sep 7

€ 176 per night