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.

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

Light-bathed comfort, wood + charm, right downtown

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.

Walk To Wilmington Village

This charming apartment is on a quiet side road overlooking historic downtown Wilmington, Vermont. Hear the church bells nearby while enjoying a relaxing evening on the deck. Take a stroll downtown and visit restaurants, shops, bars, and giftshops. Easy access to Moover, free bus to Mount Snow. Washer/dryer Smart TV with premium streaming services The front porch, side porch, and the yard on that side is all private and for you to enjoy. Please note, I live next door, and I have a dog.

The Rail Trail Retreat

Where cozy wilderness intertwines, in the heart of nature. Your exclusive 3BR/3BA lodge sitting on secluded acres in Jaffrey, NH awaits you- complete with tranquil pond, two serene decks and two spacious living room areas to gather. 10 Minutes from Mount Monadnock, adventure by day and indulge in comfort by night. Chef's kitchen, wooded views and total privacy- the perfect blend of upscale escape and outdoor adventure! Let this private space help you restore, recharge and reconnect.

Rustic 1830s Barn. Updated and funky.

Make some memories at this unique and family-friendly place. Open first floor with comfortable seating and dining space. Updated kitchen on the appliance end, and filled with almost everything you need to prepare anything from quick to gourmet meals. The second floor offers four bedrooms and a TV Room (Roku), plus a full and half bath. A refinished loft/attic can be used as an office and includes a desk|chair, some seating and a Fire TV. Bedding and towels are all cotton products.

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.

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!)

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.

Modern Shelburne house on 37 private acres.

Modern 4 bedroom home on a private mountain top with 37 acres of hiking, streams, and wildlife. The amenities are contemporary and comfortable. The views and privacy are stunning. Close to Shelburne Falls, Deerfield, Northampton and Berkshires East. Enjoy apple orchards, antiques, petting zoo, farm stands, swimming and so much more. This is a perfect family retreat offering everything you need to feel at home...while it feels a million miles away.

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.