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.

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.

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).

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.

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).

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!)

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.

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.