Smoking-friendly holiday rentals in Pioneer Valley

Historic 1840 beauty in best downtown location

Newly restored 2nd-floor apartment in 175-year-old home 2 blocks from Amherst Cinema & steps to everything this vibrant downtown has to offer. Walking distance to Amherst College and UMass. This home retains the character of days gone by, yet sparkles with new wood floors, modern bathroom & new appliances. Original wood-paneled entry hallway & exposed beams throughout. Antique furnishings, historic wall decor, and a sunny kitchen with built-in reclaimed wood bar. Small balcony w seating for 2.

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.

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.

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.

Boston Themed Retreat For 8 With Large Backyard!

Nestled in the Baystate Medical Center neighborhood of Springfield, step into the ultimate Boston sports themed house that comfortably sleeps EIGHT! You and your guests will be minutes from the Basketball Hall of Fame, MGM Springfield Casino, Six Flags, Red Rose Pizzeria, and more. This place includes free on-site parking, in-unit washer/dryer, Keurig machine, patio, grill, large backyard, and an arcade!

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.

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.