Smoking-friendly holiday rentals in Pioneer Valley

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.

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.

Glamping in the Berkshires w/ car charging station

Private cabin located in Lanesboro, MA. at the hub of cultural Berkshires, minutes from The Clark Art Institute, Williamstown Theatre and 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.

Springfield Stay for 8 with Parking & Laundry

Spacious Springfield home ideal for work crews or groups, sleeping up to 8 with a king bedroom, two full baths, and a basement with twin-over-full bunks. Features include a large kitchen with ample storage, in-unit washer/dryer, office desk and chair, TVs throughout, free parking, complimentary EV charging, and a big backyard with grill and patio seating—perfect to relax or gather after a long day. Conveniently located minutes from downtown, restaurants, and major attractions.

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.

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.

The Cottage with 4 kayaks

If you are seeking a quiet peaceful break on a beautiful lake with a quaint little cottage setting, this is the place for you. Tranquility Private parking kayaks rowboat Sit-in paddle boat. Sailboat upon request Fast internet Located on lake George in Wales, Massachusetts with a unique peninsula directly on the lake. A shady backyard with dock awaits out back. Very close to Brimfield, MA.

Rustic 1850s 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. Bedding and towels are all cotton products.