Smoking-friendly holiday rentals in Hampshire County

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.

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.

Luxury 3BR home in the forest, mins from downtown

Escape to this peaceful, light-flooded 3BR/2BA retreat on 12 acres—8 minutes from Northampton’s vibrant downtown. Watch wildlife from posh sectional sofas in the spacious living room through walls of glass, and sleep on locally made hardwood queen beds framed by a beautiful pine meadow. 2 eat-in kitchens, 2 washer/dryers, 2 bathtubs, central A/C. Hardwood floors, counters, and tables, large-screen Roku TVs and home theater projectors. A perfect mix of nature, convenience, and sumptuous luxury.

Sunny 2-floor Draper Homestead, heart of downtown

Stay in the heart of Northampton at the historic Draper Homestead, built in 1853. Once home to a prominent local family, this beautifully restored landmark is a sunny hidden gem just steps from downtown. The property offers 4 unique spaces, blending period charm with new furnishings and fully equipped kitchens. This 2-level 1BR loft apartment features an open kitchen/dining/living area with pullout sofa & 65"TV on the main floor; and an attic queen BR with desk, sitting area, & 43"TV upstairs.

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.

Sunny historic 2-bedroom in the heart of downtown

Step into the magic at this retreat in the historic 1850s Draper Homestead. Once home to a prominent local family, this beautifully restored landmark has 4 unique apartments that blend historic charm with modern comfort. This flat features 2 bdrms (Q, DBL) plus a twin-bedded alcove with Harry Potter banners, books, decor, and a TV w/ a retro game console—for the kids in your group, or the young at heart. The kitchen/dining/living area features a 55”TV for movie night after a day of exploring.

1880s sun-bathed beauty in best downtown location

Sun-drenched, recently renovated 2nd floor apartment in gracious 4-family Victorian home, steps from Northampton's vibrant downtown. Wonderful open living/dining/kitchen space w wood floors, lots of comfy couch seating, 65" 4K TV, stainless-steel appliances, butcher block counters. Master BR with queen bed, 55" 4K TV, 2nd BR with double bed. Comfy queen blow-up mattress can be set up in LR. Updated bathroom with shower and tiled floor. Washer and dryer in basement (shared with another apt).

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).

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!)