Farmstay vacation rentals in Massachusetts

Cider House Cottage

Antique guest cottage on a becountry farm property with acres of fields, ponds, forests and streams, adjoining Quabbin Reservoir domain. Ideal for hikers, bird watchers, and bicyclists, this quiet country retreat offers trails and terrain to explore, only 3 miles away from small historic New England town. Make yourself at home in the comfortably furnished post and beam home with terrace and pond views, adventure in the surroundings, dip in fresh water streams, and relax in the claw foot bathtub

Family · Location · Nearby

Flower Farm Getaway 2BR, 20 Min To Boston

Spacious two-bedroom in-law suite attached to 1700’s farmhouse, situated on our small flower farm and garden co-op just 20 minutes from Boston. Only a mile from the Mass Pike & Rt. 128 (I-95). Centrally located to all Rt. 128 businesses, colleges & hospitals. A 7-min drive to Riverside Green line “D” subway stop into Boston (parking available), or commuter rail stops (Auburndale, Wellesley & Kendal Green Stations). It's a 20-minute drive to Amtrak's "Route 128" station to NYC and points south.

Location · Value · Walkability

The 1770 House

Spring is the most dramatic time here. At the end of a dirt road with no cars or people you are one with nature. Ask to see if the pool and outdoor spa are open. In March and April our rates are discounted 20%. Enjoy our country retreat with breathtaking mountain and valley views. This expanded 1770 farmhouse gives you 4,500 sq. ft. of space for large family and friend get togethers. The house overlooks the Green River Valley with views of Vermont. There are six bedrooms and three bathrooms.

Family · Location · Biking

Farm Living

We offer a quiet country setting on a small working farm, with cows, horses, pigs, goats, donkeys, peacocks, emu, rabbits, dogs, chickens, ducks and wildlife strolling now and then. There’s opportunity to interact with the animals. Pack n play available for little ones upon request and another twin fold up bed. We truly want all of our guest to enjoy all the farm has to offer and enjoy the peacefulness. Please inquire about kayak rentals. We also have a game room available to rent. See photos

Value · Family · Kitchen

Brooksong, the perfect Berkshires getaway

Part of this bright, sprawling, five-acre property was built in 1866 as a schoolhouse. Its historic charm now includes all the updated comforts of home, in an idyllic country setting that's lovely in all seasons. Located a short drive from Jiminy Peak, Brooksong is perfect for a ski vacation and close to plenty of lakes for summer fun. With a pool table, fire pit, and play set for kids, this is the perfect place to recharge and have fun with the people you care about. Welcome to Brooksong!

Value · Location · Amenities

Zen Inspired Retreat with Private Forest Trails

Zig-Zag Trails blends modern comfort with the charm of rural living. Set on 65+ acres of private meadows and forests, our master guest suite is the perfect retreat to relax and recharge. Explore scenic zig-zagging trails, perfect for hiking, mountain and E-biking, and unwinding in nature—a haven for outdoor enthusiasts and homebodies alike. 📍 1 hour from Boston 📍 35 minutes from Providence 📍 25 minutes from Worcester Escape to Zig-Zag Trails—where tranquility meets adventure.

Family · Location · Air conditioning

Sunny Chalet Nestled in the Woods of Ashfield

Relax in a quiet sunny chalet located on land with established herbal gardens, offering privacy, space, and a comfortable base for families and small groups visiting Ashfield and the surrounding hills. This pet-friendly three-bedroom home is designed for guests who want a peaceful, rural stay with the reassurance of an attentive host nearby. Whether you’re visiting family, exploring the area, or enjoying time away from the city, the chalet offers room to unwind in a calm setting.

Value · Location · View

Winery Farmhouse w/ Private Hot Tub & Wine Tasting

Vineyard Retreat. Stay at the newly remodeled Ice House, a luxury farmhouse at historic Marble Ridge Farm (est. 1680). This light-filled 3-bedroom home is perfect for bachelorette weekends, bridal party get-ready, or group getaways. Enjoy the private hot tub, beautiful natural light, and a peaceful winery setting just minutes from top-rated restaurants, shopping, and major highways. Your stay includes a complimentary wine tasting and 10% off all wine bottle purchases.

Family · Location · Outdoor spaces

Bedroom Forest View I Sauna I Fire-pit I Trails

Escape to a secluded custom built tiny house nestled amongst old pines and the Umpachene River. Inside, rustic charm meets modern comfort with 2 lux queen-sized beds, a well-equipped kitchen and bathroom, a massive bedroom forest view and a private sauna. Outside the home you can find a cozy fire-pit, trails that lead down to the river, and a dining table for all your meals. Go out for a day of hiking and exploring, and come back to unwind to sounds of nature.

Value · Family · Walkability

A Country Retreat-Enhanced Studio Apartment

Welcome to our lovely apartment, located in the beautiful, quiet Western MA hill-town of Conway. This is our second time as Airbnb hosts, having hosted almost 150 reservations and achieved Superhost status there. We built again and downsized but included this spacious studio apartment with a bedroom alcove. Wooded and quiet yet just 3 miles from the charming tourist town of Shelburne Falls, and not far off RT91 and the cities of Amherst, Northampton and Greenfield.

Family · Location · Parking

Farm stay in a Historic Ski Lodge turned Barn

Once a ski lodge, then a horse barn, the hayloft in this unique stone barn has been converted to a comfortable & peaceful getaway. Enjoy a tranquil farm stay on a working Lavender farm. Help feed (if you wish) the horses and ponies and see the chickens. Enjoy the serene views and take in a sunrise or sunset or the stunning evening stars and moon on the back patio, stroll around the farm and hike our 1 mile nature walk. Convenient to local skiing & golfing.

Location · Family · Wifi

Quiet country retreat with modern conveniences

Our mountain-view farmhouse sits on a 5 acre knoll, 300' from a quiet country road, surrounded by the sights and sounds of quintessential New England. The location of the property strikes a perfect balance between seclusion and convenience with access to hiking, kayaking, biking, parks, restaurants, grocery, and shopping close by. Restaurant food delivery of local favorites for Japanese (including sushi), Chinese, pizza, sub, salads, etc is available.

Family · Value · Accuracy