Smoking friendly vacation rentals in Hampshire County

Find and book unique smoking friendly rentals on Airbnb

Top-rated smoking friendly rentals in Hampshire County

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

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Guest favorite

Rental unit in Northampton

4.97 out of 5 average rating, 252 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.

Superhost

Rental unit in Northampton

4.87 out of 5 average rating, 141 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.

Guest favorite

Rental unit in Northampton

4.98 out of 5 average rating, 169 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.

Guest favorite

Home in Plainfield

4.73 out of 5 average rating, 151 reviews

Western MA quiet with BBQ's, Wi-Fi, pond & kayaks

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

Rental unit in Amherst

4.91 out of 5 average rating, 183 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.

Cottage in Plainfield

4.8 out of 5 average rating, 40 reviews

Windsor Pond spacious get-away cottage

I first would want all to know that this cottage is not winterized & only available from june til mid oct. Im ready to take reservations for next year.... The cottage is quite large. We have a large indoor porch surrounded by large windows, a table that turns into snooker or some fun poker.. Many different chairs and a couch for relaxation or loads of fun.. also a outside porch with picnic table. Large dining room table for eats or board games. Direct tv is available. washer and dryer.

Guest favorite

Rental unit in Northampton

4.95 out of 5 average rating, 201 reviews

Wood, sunshine & movies in best downtown location

Sun-drenched 1st fl apt in 2-family Victorian, steps from Northampton's vibrant downtown. 2 spacious queen bedrooms, 1 bedroom/study with pull-out king. Pine-paneled kitchen with breakfast bar; open living/dining room; stereo with turntable and vintage record collection; home theater with projector. Private deck. Wood floors throughout apartment. 42" HDTV in master bedroom. Hi-speed Internet. Laundry room in basement with washer/dryer (shared with upstairs apt). Shared heated pool (Mar-Nov).

Guest favorite

Home in Chester

4.98 out of 5 average rating, 42 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

Guest favorite

Rental unit in Northampton

4.93 out of 5 average rating, 174 reviews

Light-bathed 3br w porch in best downtown location

Sun-drenched 2nd fl apt in 2-family Victorian home, steps from Northampton's vibrant downtown. Three spacious bedrooms: 2 with queen beds & a third with a double. Central eat-in kitchen with dining table, gas range and small dishwasher. Expansive south-facing living room with two couches and 42" smart HDTV. Private porch overlooking quaint tree-lined street. Wood floors throughout apartment. Hi-speed Internet. Laundry room in basement with free washer/dryer (shared with downstairs apt).

Guest favorite

Home in Ashfield

4.95 out of 5 average rating, 57 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

Home in Amherst

4.91 out of 5 average rating, 65 reviews

1840 two-family home in best downtown location

This 3-bedroom, 5-bed house sleeps up to 10 -- ideal for groups that wish to rent both of the apartments in an historic 2-family home in downtown Amherst, steps away from everything this vibrant downtown has to offer. 3 bedrooms, 5 beds. 5-min walk to Amherst College, 15-minute walk to UMass. New comfy mattresses with all-cotton linens, eclectic decor. Two kitchens. Washer/dryer. Large-screen TVs in both apts. Front porch with rocking chairs, balcony, and backyard.

Guest favorite

Cabin in Chester

4.96 out of 5 average rating, 52 reviews

2 Rustic Cabins on 68 Secluded Acres

Visit Caterwaul Cabin and enjoy an elevated camping-style experience on 68 private acres in Chester, MA - with most of the amenities of home. New for 2024, Helter Shelter - a separate tiny cabin companion to the original property - included in the rental cost and ONLY rented together. A perfect getaway for outdoors-minded folks, searching for solitude and privacy, a launching pad for an ideal weekend in the Hilltowns / Berkshires or a weekend away from it all.