Family-friendly holiday 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

Beautiful, Unique, & Cozy Cedar Flat

Come enjoy this new and beautifully designed space in historic Uxbridge, MA. Set up like a tiny house, it is the most cozy and clean place you will visit. A ship’s ladder will take you to the queen loft bed or use a new PotteryBarn sleeper sofa. The Frame TV will act as a beautiful painting if you prefer to "unplug." Climate control and a hammock chair are a perfect combo! Located on a quiet street, it is an easy 25 min. drive to Providence or Worcester, and only 50 min. to downtown Boston.

Cozy en suite w/ high ceilings

 Relax in this peaceful private en suite with breathtaking backyard views of the tall pine forest. Lots of natural light fills the space with room darkening shades to sleep in. Enjoy cozy nights by the fireplace and a well stocked granite kitchen. Great location only minutes to the Mass Pike. 25 min to Boston. 30 min. to Foxboro Stadium. Enjoy shopping at the Natick Mall, AMC movies, tons of diverse dining & grocery options. Backyard has firepit for outdoor eves. Safe walkable neighborhood.

Just Be Cabin

Small, rustic cabin in the woods behind our home. The cabin has electricity, but no running water. Drinking and cooking water are provided from a hand pumped container. The cabin is a beautiful place to slow down, connect to nature and one's self. If you love to camp, you will love the cabin. It is the perfect locale for a personal retreat. We are happy to arrange a yoga class at our home studio as well. It is like a tree house, where all are welcome to come, simplify life and just be.

The little house on Mirror Pond

Escape to our fully renovated tiny pond house on the serene Mirror Pond. Perfect for up to 4 guests, enjoy swimming, kayaking, or floating on tubes. Unwind by the fire pit, barbecue on the deck, or cozy up by the fireplace (our apologize but it is currently not working) with board games on cooler days. With great WiFi, it’s also ideal for a peaceful work retreat. Whether you're here to relax, or get some work done, this tranquil hideaway offers the perfect blend of adventure and relaxation.

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!

Stylish and Cozy at Revere Beach

Unwind in the stylish Studio apt in the heart of Revere. Enjoy the apartment all to yourself and your family. The city is full of award-winning restaurants, bars, shops, historic landmarks, and attractions. Adventure through Revere and the metro Boston region easily from this prime location with very close walking distance to Blue Line subway station and Revere Beach. ✔ Fully Equipped Kitchen ✔ Comfortable Bedroom w/ Full Bed ✔ Office Desk ✔ High-Speed Wi-Fi ✔ Free Parking ✔ Pool ✔ Gym

Tiny farm house on horse farm

Set in a quiet cul-de-sac at the end of our driveway, this tiny house is part of our family compound and working horse farm. We have many animals. Enjoy your space, knowing we are just 50 yards away should you need anything. This is a true tiny house experience. The kitchenette has everything you need. The sleep loft is accessible by a ladder and has a low ceiling. Disclaimer there is no door on the toilet, which is tucked away in the kitchen area. WiFi connection is not guaranteed.

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!

Water front cabin-like guest suite on a quiet pond

Our home is located on a wooded lot overlooking a pristine kettle pond. Access to our home requires ascending a long but gradual set of stairs followed by a second set of stairs to the entrance of the guest suite. The two room suite has a bedroom and a kitchenette with a microwave, toaster, electric kettle and mini frig. There is a French press, coffee bean grinder, tea, cups, dishes and flatware in the cupboards. It does not have a full kitchen ( no stove/ no kitchen sink)

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.