Holiday houses 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

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Lakefront, view of ski mtn, fireplace, sauna

Direct lakefront with panoramic views of Wachusett Mountain (#1 skiing in MA). In the summer, enjoy the kayaks, canoe, paddle-boards, motor boat. In the winter, cozy up next to the fireplace and enjoy a complimentary bottle of wine. In the fall, gaze upon the breathtaking foliage from the sunroom. Outdoor shower, dock, firepit, hammock, bike, washer/dryer, desk, sauna, dishwasher, linens, kitchen amenities. Our other lakefront house is down the road: www.airbnb.com/h/lakefrontmountainview

Cozy Hilltown Cottage

Enjoy a peaceful stay in this cozy, creative space. Set on 10 acres of gardens and woods, this cottage is perfectly located to explore Western Massachusetts - with places like MASS MoCA, Shelburne Falls, Tanglewood and Northampton all within a 30min to 1 hour drive. Upstairs is a queen bed and full bath, while downstairs features a functional kitchen, work desk, grand windows, and a living space with full sleeper sofa. We live in the main house on property but respect your privacy-see photos!

Entire Historic Carriage House with Fireplace & AC

Escape to our charming Carriage House in the Historic District of Sherborn which offers the feel of a country retreat without being far from civilization. Great for travelers looking for a peaceful getaway, checking out nearby colleges or attending a celebration like a wedding or graduation. You will love the feel of the Carriage House, its spacious living and dining room, well-equipped kitchen, and the beautiful grounds. Check us out on IG @carriagehousema. NEW in 2022: Mini-split AC!

Cozy Lake Cottage: Hot Tub, Gym & Waterfront Views

Welcome to our charming 3-bedroom lake cottage in Mendon, MA, where every sunrise paints the sky with breathtaking hues over tranquil waters. Accommodates 6 guests, making it ideal for families or couples seeking serenity. Enjoy lakeside coffee, fishing, kayaking, and evenings by the fire pit. We are pet-friendly, so feel free to bring your dogs along — if you have more than 1 dog, please let us know. Conveniently located near restaurants and attractions. Book now for a magical getaway!

Modern Luxury Apt. | 7 min from Commons

This luxury 1Br + 1bth apartment is the perfect getaway. - 650 square feet, newly renovated - 15 Minutes from Old Silver Beach, South Cape Beach, and Falmouth Heights beaches - Steps from 1,700 acres of walking trails (Crane Wildlife) - 7 minutes to Mashpee Commons (shops and restaurants) - 15 minutes to Main Street Falmouth - 13 minutes to Ferry for Marthas Vineyard - 85” smart TV - 5 minutes to Shining Sea Bike Trail - Coffee/Espresso Machine - 2 minutes from Paul Harney Golf Course

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.

Winery Studio w/ Private Hot Tub,Fireplace,Tasting

*A North Shore Favorite!* This former art studio is breathtakingly beautiful and is a true getaway to relax and feel at peace. It has great lighting and is located directly off of one of our historic barns. The space is perfect for a romantic retreat or the traveling professional looking for a place to call their home away from home. Located in an affluent neighborhood, minutes away from shopping and restaurants. Booking includes a wine tasting and 10% off all wine purchases!

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.

Hipster Basecamp | Modern • Fireplace • Parking

Welcome to Hipster Basecamp, a curated space where mid-century design meets modern comfort. Whether you're here for business or pleasure, enjoy bold touches like a double-sided fireplace, Smeg appliances, and a ceiling-mounted rain shower. Brew espresso or mix cocktails with everything at your fingertips, then head to the deck to unwind and take in the peaceful view. Admire original artwork throughout — and if a piece speaks to you, it's available for purchase.

The Writer's Retreat: A Sweetwater Stay

Located on the shore of Tully Pond, The Writers Retreat is a newly designed 325sqft lake side cottage with breathtaking views of Tully Mountain. This 4-season cottage is built with salvaged barn wood; up-cycled maple floors and custom built furniture and lighting. It's the little sister to The Fishing Cottage. You'll find this intimate home has everything you need to relax, write the next Great American Novel, connect with a lover, or just plain chill.