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

Apartment in Northampton

4.99 out of 5 average rating, 218 reviews

Skylights, art + design in best downtown location

Elegant spacious sun-drenched 2-bdrm penthouse in 4-family Victorian on tree-lined street in downtown Northampton. Easy walk to Smith campus. Skylights; large tiled bathroom w/ shower, jacuzzi tub, washer/dryer; renovated kitchen with Italian-tiled floor; open floor plan with ample dining area; living area with large leather couch, handmade rustic wood coffee table, lg TV, Yamaha digital piano, cathedral ceiling, and glass doors onto a balcony. Home theatre in master bedroom. Off-street parking.

Top guest favorite

A young child stands in a shallow swimming pool, surrounded by greenery and wooden fencing. Sturdy handrails provide support for entering and exiting the pool area. The bright sunlight casts playful reflections on the water's surface.

Apartment in Northampton

4.98 out of 5 average rating, 309 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

An attractive, multi-story building stands on a tree-lined street. The exterior features light grey siding and white trim, with a welcoming front porch. Lush green bushes provide a natural border along the pathway leading to the entrance, enhancing the inviting presence of the home.

Apartment in Northampton

4.9 out of 5 average rating, 193 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.

Home in Plainfield

4.74 out of 5 average rating, 157 reviews

Summer spectacular w kayaks, WiFi, BBQ & 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.

A serene lakeside scene features individuals relaxing on grassy terrain, with colorful inflatable floats nearby. A picnic setup is present, complemented by trees lining the water's edge, providing a peaceful, nature-filled backdrop.

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.

Superhost

A dedicated study area features a wooden desk and ergonomic chair, positioned next to a large sliding glass door. Outside, a deck is visible, with snow covering the furniture. Natural light fills the room, enhancing the warm tones of the walls.

Apartment in Northampton

4.93 out of 5 average rating, 240 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

A workspace is displayed adjacent to a large glass door leading to a snow-covered deck. A wooden desk is positioned with an office chair, offering a view of outdoor seating arranged on the patio beyond.

Home in Northampton

5 out of 5 average rating, 14 reviews

Sun-drenched 6BR Victorian steps from downtown

A light-flooded 6-bedroom, 2-family Victorian, steps from downtown Northampton and the Smith gates. Walk 5-10min to many great restaurants, cafés, and shops. Your 2-floor house has 3 bedrooms downstairs and 3 upstairs; a large private patio with outdoor dining table; and a street-facing balcony. There are 2 spacious living rooms (one with HD projector and one with HDTV), 2 eat-in kitchen, and a vintage stereo system w/vinyl collection. Shared gardens include heated pool and kids' play area.

Guest favorite

Apartment in Northampton

4.94 out of 5 average rating, 224 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).

Top guest favorite

Two red Adirondack chairs are positioned beside a natural stone fire pit, surrounded by a grassy area. A tranquil pond is visible in the background, bordered by lush greenery and wildflowers, creating a serene outdoor space for relaxation.

Home in Ashfield

4.96 out of 5 average rating, 68 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

4.9 out of 5 average rating, 86 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.

A serene stream meanders through a wooded area, flanked by large rocks and forest floor covered with moss and fallen leaves. The surrounding trees provide a natural frame, with varied shades of green and brown reflecting the tranquility of the secluded landscape.

Cabin in Chester

4.96 out of 5 average rating, 56 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.

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

4.78 out of 5 average rating, 223 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. Just 5 min to I-91 and Pike, 15 min to Northampton.