Smoking friendly holiday rentals in Pioneer Valley

HideAway UConn Coventry RockFarm BnB Breakfast A+

Welcome to “The Hide Away” on Rock Farm with Superhosts Jon & Jeri. A private, family-friendly 1000+ sq ft wooded retreat featuring two bedrooms, 500 Mbps WiFi, Roku TV, private deck, full kitchen, laundry, and DIY breakfast. Just 15 minutes to UConn and 2 minutes to Bolton Lakes for fishing and hiking. See our VIP Guest Book for local favorites. Clean, cozy, no-shoe secluded BnB — 5⭐️ guest favorite. Ask about “The GetAway” too! It’s our King Studio Suite, a private space, perfect for couples.

1880s skylit design apt w balcony, best 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.

Tiny house on the river

Welcome to your perfect New England getaway! This tiny home is an ideal home base for exploring the Ashuelot River (direct access on the property). A short walk to the Denman Thompson covered bridge and access to the Ashuelot rail trail. Note: Unfortunately, there is NO shower. Limited cold water very rustic but comfy. Shared land with the homeowner and family. Friendly pets are also on the property and welcome. You also have access to the land and what's on it. including kayaks License #106255

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.

Glamping in the Berkshires w/ car charging station

Private cabin located in Lanesboro, MA. at the hub of the Berkshires, The Clark Art Institute, Williamstown Theatre, Jiminy Peak & Mass MoCA . Nestled at the base of Mt. Greylock, attractions include Barrington Stage, Shakespeare & Co, The Colonial Theatre, Tanglewood, The Norman Rockwell Museum, Jacob's Pillow, The Theatre Barn, Canyon Ranch, Naumkeag and many others. Located close to Ashuwilticock Rail trail, the Appalachian trail and hiking trails on Mt. Greylock Reservation.

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.

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. 3rd and Top floor is strictly for guests only. Just 5 min to I-91 and Pike, 15 min to Northampton 15 min to Big E.

Walkable Modern 2BR in Downtown - Left Unit

Enjoy a bright, modern 2-story apartment in the heart of Bennington. Walk to cafés, shops, and local restaurants, and reach Walmart and Hannaford within minutes. Close to ski areas, mountain hikes, the Bennington Battle Monument, and stunning fall/winter scenery. A cozy, convenient home for both short and extended stays—perfect for families, professionals, and travelers exploring Vermont.

Tiny Cottage on Spofford Lake

This perfect spot on Spofford Lake will have you coming back every year to make memories without giving up the comfort of home. There's so much to enjoy: from a cup of coffee sitting on the beach, to swimming, kayaking, enjoying sunsets while making s-mores for the kids at the campfire, grilling burgers with family and friends, and even streaming your favorite shows on a rainy day.

Modern Industrial Apartment with rooftop access

* Modern industrial apartment with rooftop access. * Nestled in an old Mill Building/Artist Community. * Centrally located between Boston and NYC. * 15 mins to UConn, 20 mins to Brimfield Antique Show. * 40 mins to MGM Casino in Springfield, MA. * Walk to restaurants, boutiques, parks, and events. * On-site Yoga, Dance, Recording Studio & Vintage Shop.

Quaint cozy vermont apartment

My place is close to parks, great views, restaurants and dining, art and culture. You’ll love my place because of privacy the sky lights, high ceiling, the comfy bed, the kitchen, the neighborhood, and the outdoors space. My place is good for couples, solo adventurers, business travelers, families (with kids), and furry friends (pets).

Roaring Fun!

Reconnect with nature at this unforgettable escape. A perfect spot in the Roaring Brook Co-op campground. Enjoy unlimited use of our 2007 (she’s old but comfortable) 30’ RV, golf cart and all the park amenities. Pool, two lakes, tons of games and activities, playgrounds and outdoor movies to name a few.