Smoking-friendly holiday rentals in Hampden County

Ghost Shadow Farm

A timeless slice of New England charm with all the modern amenities you need for pleasure travel or work-stay. Private entrance, ample off-street parking, and spacious guest-exclusive areas including library, magnificent granite fireplace, dining area w/complimentary breakfast, TV/workout room, & beverage station. Choose from queen-size Blue Room or king-size Fern Room (children's annex available on request). Explore 11+ acres with spring-fed swimming pond, mature fruit trees, and much more!

1880s sun-bathed beauty in best downtown location

Sun-drenched, recently renovated 2nd floor apartment in gracious 4-family Victorian home, steps from Northampton's vibrant downtown. Wonderful open living/dining/kitchen space w wood floors, lots of comfy couch seating, 65" 4K TV, stainless-steel appliances, butcher block counters. Master BR with queen bed, 55" 4K TV, 2nd BR with double bed. Comfy queen blow-up mattress can be set up in LR. Updated bathroom with shower and tiled floor. Washer and dryer in basement (shared with another apt).

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.

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.

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.

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.

Queen size bed at an old Victorian.

Old Victorian Mansion you can enjoy. The rooms are spacious and there are two dedicated bathrooms only for airbnb guests. bathrooms here are at the end of the hall for you to use. The house is near 291 highway and you will not take long to get to most attractions such as Six Flags, Basketball Museum, Big E, etc. The bed is a queen size memory foam mattress. We have WiFi, and a flat screen 4K smart tv you watch Netflix, YouTube, etc.

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!

The Cottage A whole season rental

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.

OrchardSlope

"The best of the "feel right at home" AirBnb experiences. Loved it." Former guest of OrchardSlope "The Art of Hosting as an emerging peace practice - the art of caring for." Toke Moeller OrchardSlope is a single family home where we welcome and share with our Airbnb guests. Disclaimer: New photos taken with wide-angle lens are somewhat distorted. Thank you!

Northampton Sunny Bedrm - Workspace & Private Bath

Relax at this unique and tranquil getaway in Northampton, home of Smith College (6 bks away). Small, quirky city w/ boutique shops & fab restaurants downtown (10 blks away). Bike trails (w/ entrance one blk away) go all around the area. Located within a few blocks from hospital (Cooley Dickinson) & park (Child's). Perfect for short or longer stays.