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.

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.

Beautiful Farm Vacation House

Beautiful Farm Vacation House 3 Bedroom, 2 Bath, Sleeps 6-8, Gorgeous View, Open Fields Close to Berkshire East, Mt Snow, Zoar Outdoor , Crabapple Whitewater, fishing in the Deerfield River. Wonderful for artists, children and adults alike. 25 acres of meadows and woods with a stream below. Free-ranging chickens and sheep. Large, well-equipped kitchen. Game room with ping-pong and pool table. Large rooms for entertaining. Nearby Pelham Lake and Harriman Reservoir for swimming.

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.

Cozy Cabin Retreat in the Berkshires

Welcome to Otis, Massachusetts, nestled in the heart of the beautiful Berkshires! This newly renovated, 3 bedroom cozy cabin sits on a peaceful 2-acre lot surrounded by trees, just steps from some of the state’s most stunning waterfalls, hiking trails, lakes, and more! Whether you're seeking a quiet, romantic retreat to unwind to the soothing sounds of nature or planning a fun-filled family getaway, this cabin is the perfect escape.

Bergills’s Basecamp- Matty B’s Putting Green

**This is an upper CAMPSITE ⛺️ in our backyard closest to the house. There is NO access to the house or its facilities** Originally a classic New England farm, this property feels secluded and private but is centrally located in Suffield, CT. In a former life, I owned a hostel with shared bunk and private cabin accomodation in the North Cascades of Washington State. I love hosting guests of all kinds and from all places!

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.