Family-friendly holiday rentals in Canaan

Trailside Stays - Tiny House in the Woods-Escape to Nature. Snow Owl

This charming and elegant little cabin will transport you into nature. The feeling of camping outdoors with indoor amenities. Part of the brand-new campsite, Trailside Stays that is conveniently located alongside the ski and mountain bike trails at Green Woodlands. This tiny house features 1 high quality queen-size bed, linens, kitchenette, large picture windows, bathroom with shower, heating and A/C, outdoor seating and grill top fire pit. Don't see your dates available? Check the other cabins!

Stylish Vermont Cabin | Views · Trails · Luxe

Combining sweeping views of distant hills with complete privacy and wraparound porches on two sides, the Red House is a custom cabin built for couples and smaller families. Surrounded by working farms and within easy reach of trailheads to hike or bike Mt Ascutney, or to visit Woodstock, Hanover, Ludlow and the Upper Valley, the Red House sits among some of the best restaurants in Vermont and awaits the discerning traveler who has earned the right to do absolutely nothing and experience it all.

Cozy A Frame Cabin

Discover Your Dream Getaway at Our Enchanting A-Frame Cabin in Danbury, NH! Hike lush forest trails, paddle across sparkling lakes, or hit the nearby slopes for seasonal adventure. After a day outdoors, kick back on the spacious deck, fire up the grill, and dine under the stars. Whether you're planning a romantic escape or a fun-filled family getaway, this hidden gem offers the perfect blend of comfort, charm, and natural beauty. Escape the ordinary—book your unforgettable Danbury retreat today!

Quiet lakeside retreat with private dock.

Welcome to our charming lakefront home nestled in the tranquil beauty of nature! Situated at the water's edge, our rental boasts a private dock, providing convenient access to the pristine lake for fishing, swimming, or simply enjoying the outdoors. Inside, you'll find two bedrooms comfortably furnished with a total of three beds, ensuring a restful night's sleep for up to six guests. With close proximity to Cardigan Mountain school Dartmouth & DHMC campuses, your home away from home awaits!

Private, 1 bedroom boutique tiny home

This boutique tiny home is situated in the picturesque Upper Valley of Vermont. The nearly 50 acres of private land is equal parts woods and water. You will wake to the mooing of dairy cows. Have your coffee on the porch while watching birds dive for their breakfast on the pond. Inside you will find every modern amenity. A fully appointed chef's kitchen. A living area filled with comfy furnishings and a cozy fireplace. Upstairs is a queen bedroom with an ensuite double showered bathroom. Heaven!

Beautiful post & beam loft apartment

This unique loft apartment, on 70-acres, is a quiet “getaway” designed for relaxation, recreation and restoration. Also excellent for remote work. Apartment is defined by its beautiful post-and-beam architecture and light-filled space. Includes: * private bedroom * large open-plan living room with sleeping nook, dining area, smart TV * dedicated workspace * well-equipped kitchen w/ new appliances * bathroom with bath/shower Above the garage, apartment has a private entrance with keypad.

The Willow House: a Modern Vermont Retreat

Just 7 miles (12 minutes ) to the Dartmouth Campus, this newly re-built little house sits beside its own pond on the edge of a sheep pasture. All the comforts of a modern home in 600sqft. Enjoy access to hiking trails and State Forest lands as well as an easy drive to world-class skiing an hour away and all that the Dartmouth College community offers just minutes away. This is the best of pastoral Vermont, with outside living-dining space ( south facing deck and north facing screen porch).

Kolelemook Cottage!

Kolelemook Cottage - a peaceful lakeside retreat that offers something for everyone all year round. With pristine and shallow water, this lake is perfect for family recreation. We offer an inflatable swim platform, children and adult kayaks, as well as a paddle board for seasonal enjoyment (available Memorial Day-October 15). Board games and Smart TV for indoor entertainment. 10 min. to downtown New London, 20 min. to Sunapee Ski Resort, with loads of hiking options just a short drive away.

Mountain Lodge with Private Sauna

Escape to Darkfrost Mountain Lodge, less than 2 hours from Boston - Gather under the stars by the fire pit & garden - Relax or grill on patio with woodland views - Enjoy a pet-friendly working homestead - Ski at nearby Ragged & Tenney Mountain - Explore hiking, biking & snowshoeing nearby at Wellington, Cardigan Mountain State Parks, AMC Cardigan Lodge Looking for options? Visit my Airbnb Host Profile to explore our 3 available cabins: Millmoon A-Frame, Black Dog Cabin, Darkfrost Lodge.

Cozy Luxury Cabin in Dorchester

Enjoy peace and quiet in the woods of Dorchester, at the foothills of the White Mountains! Elevated treehouse-style Cabin approximately 600 feet from the owner's main house. Tucked in the woods you will enjoy nature surrounded by moose, bear, deer, ermine, and more, while being only 15 minutes away from Plymouth. Close to Rumney Rocks climbing and countless hiking trails. Direct access to the amazing Green Woodlands for mountain biking in the summer and cross-country skiing in the winter.

Gorgeous, clean studio in brand new building.

Enjoy a well-lit, beautiful stay in the heart of White River Junction. Queen size bed and new construction (2021). Walking distance to restaurants, bars, art galleries, and all this historic town has to offer. Within a 3-min walk: Tuckerbox, Wolf Tree, Big Fatty’s, Northern Stage. 10 min: King Arthur Baking 10 min: Dartmouth College 15 min: Dartmouth Hitchcock Medical Center 25 min: VT Law School Perfect, cozy place for visiting parents, traveling nurses, professionals, etc.

Cabin on the Hill

Enjoy a stay in the hills of Vermont - glamping at its finest! A 5-10 minute hike UPhill to a secluded getaway in the heart of Vermont. Amenities include a quaint outhouse, a unique outdoor shower, a 2 burner outdoor gas stovetop and a fire pit to roast marshmallows. The 12x14 screened in cabin with ladder accessed loft sleeps 2 comfortably. Don't worry about bringing pots and pans - cabin is equipped with dishes and a water supply. Adjustable LED lights to light up the night.