Family-friendly holiday rentals in Canaan

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Canaan

Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

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Top Guest favourite

A serene lakeside setting is presented, featuring a stone patio bordered by natural boulders. Colorful adirondack chairs in blue and green invite relaxation. A wooden dock extends into the calm water, with trees and hills visible in the distance under a cloudy sky.

Home in Enfield

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!

FamilyIndoor spacesAccess

4.95 out of 5 average rating, 131 reviews

Guest favourite

A comfortable living area is highlighted by a light beige sofa and a round blue ottoman. A flat-screen TV is mounted above a traditional fireplace. Natural light is welcomed by large windows, contributing to a bright and airy feel.

Home in Lebanon

Benton House, Sleeps 10, King Bed Primary

Private 5 Bedroom home, 9 mins to Dartmouth-Hitchcock Medical Center. Your family and friends will be close to everything when you stay at The Benton House. Embrace the calm of the neighbor hood with an evening walk or campfire. Visit the park at the end of Lilac Ave. Ride a bike, snowshoe or snowmobile on the local rail trail. Read a book in the greenhouse. - 6 beds - Full Kitchen with dishwasher - Washer and Dryer - WiFi and 2 Flatscreen TVs - 2 car indoor parking with 4 driveway spaces.

KitchenFamilyLong stay

4.87 out of 5 average rating, 156 reviews

Top Guest favourite

Home in Woodstock

Cape Cod Home in Woodstock, Pet-Friendly & Wooded

Welcome to this charming 4-bedroom Cape Cod-style retreat in Woodstock, Vermont, a picture-perfect New England getaway set on a wooded hillside lot. With original wide-plank hardwood floors, a fully equipped chef's kitchen, and a spacious back deck with a 6-burner propane grill, this home offers the perfect blend of rustic character and modern comfort. Explore the covered bridges and artisan shops of Woodstock Village, or simply unwind in the peaceful garden setting. Please see: Other Things to

KitchenFamilyCleanliness

4.99 out of 5 average rating, 170 reviews

Superhost

An A-frame cabin showcases a wooden exterior with large glass windows, allowing natural light indoors. The deck features four Adirondack chairs arranged around a circular fire pit. Surrounding greenery and autumnal trees enhance the serene outdoor setting.

Cabin in Danbury

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!

Indoor spacesFamilyWi-Fi

4.94 out of 5 average rating, 152 reviews

Guest favourite

Tiny home in Dorchester

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!

KitchenIndoor spacesCondition

4.95 out of 5 average rating, 230 reviews

Top Guest favourite

The bright kitchen showcases a spacious island with seating for four at sleek, modern bar stools. Stylish pendant lights hang above, and large windows provide natural light. Ample cabinetry lines the walls, with contemporary appliances positioned for easy access.

Home in Hartford

Quechee Getaway Book Your Ski Trip Now

New Build Multi family friendly home near Woodstock, Killington and Dartmouth – Sleeps 12, Modern Aesthetic, Private Porch & Fire Pit Escape to this stunning modern ski home, just 25 minutes from the Skyship Gondola of Killington, Vermont. Whether you're hitting the powder in winter or enjoying the breathtaking foliage and outdoor adventures in the warmer months, this luxurious retreat offers the perfect base for your next getaway. Hike the Gorge or stroll thru the quaint village of Woodstock.

Indoor spacesKitchenAir conditioning

4.94 out of 5 average rating, 133 reviews

Guest favourite

The cabin features a gabled roof and large front windows, allowing natural light to fill the space. Surrounded by tall trees, the tranquil approach showcases a well-maintained pathway leading to the entrance, with soft sunlight filtering through the foliage.

Cabin in Grafton

Nature cabin | fire pit, fireplace, yard + privacy

The WildeWoods Cabin is a sunny open-concept cabin with cathedral knotty pine ceilings & exposed beams; renovated with comfortable furnishings, modern amenities, vintage décor & a gas fireplace (on/off switch!). Enjoy peace & privacy on 1+ acres; the cabin is set back from the road and surrounded by yard, gardens, & tall trees. Nestled in the foothills of Cardigan & Ragged Mountains; there are endless outdoor activities nearby. Up to 2 dogs are welcome with pet fee. IG: @thewildewoodscabin

FamilyKitchenView

4.98 out of 5 average rating, 235 reviews

Top Guest favourite

Cabin in Alexandria

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.

Indoor spacesKitchenSkiing

4.98 out of 5 average rating, 332 reviews

Top Guest favourite

The living area features a blend of warm wood paneling and natural light. A large sectional sofa is complemented by a comfortable armchair, with a coffee table positioned nearby. A desk is visible, offering a workspace, while a decorative rug adds texture to the floor.

Cabin in Dorchester

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.

KitchenIndoor spacesParking

5.0 out of 5 average rating, 128 reviews

Top Guest favourite

The living area features a high, wooden ceiling with large windows that provide natural light and views of the surroundings. A stone fireplace is positioned centrally, flanked by comfortable seating. A dining area and modern kitchen appliances are visible in the background.

Home in Hebron

Newfound Lake Log Home | Hot Tub & Lake Views

Escape to Eagle Ridge, a Top 1% Airbnb log home overlooking beautiful Newfound Lake and featured in Log Home Living Magazine. Relax in the private hot tub, enjoy spectacular lake and mountain views, visit the Hebron town beach less than 1/4 mile away, or unwind by the fireplace. Set on 3.5 private acres, Eagle Ridge accommodates up to 6 guests with three bedrooms and two full baths. Enjoy central A/C, a screened porch, large patio, gas grill, high speed WiFi and whole house generator.

Indoor spacesFamilyComfort

4.99 out of 5 average rating, 184 reviews

Top Guest favourite

The private guest house is surrounded by lush greenery, featuring a covered porch with a chimney and hanging planters. A well-maintained lawn leads to the house, while a backdrop of rolling hills enhances the tranquil setting.

Cottage in Windsor

Ogden's Mill Farm

Private guest house situated on over 250 acres, with fully equipped gourmet kitchen and great views of quiet fields and valley. Pond with diving board for swimming in the summer. Giant sledding hill is a favorite of children and adults alike. Trails on property for hiking, xc- skiing, and snowshoeing. 15 mins to Woodstock VT. 45 mins to Killington,Pico and Okemo. Great restaurants and shopping nearby. Hanover and Norwich VT 20 mins. Please note not handicapped accesible.

Indoor spacesKitchenQuiet

4.97 out of 5 average rating, 464 reviews

Guest favourite

The main living area features high wood-paneled ceilings, large windows showcasing views of the wooded surroundings, and a cozy wood burning stove. A mix of seating options, including a couch and chairs, are complemented by a dining area and a coffee table at the center.

Cabin in Eastman

Cozy Eastman Cabin

Come stay at this cozy modern cabin in the Eastman community on a private 4-acre lot overlooking a heavily wooded forest. Large windows facing the woods let in a ton of light and make you feel like you’re in the treetops. The house is perfect for a small family getaway or a couples retreat. Go for a dip in Eastman Lake down the road or explore hiking and biking trails which are plentiful and nearby. Please note, 4-wheel-drive may be necessary in certain weather conditions.

KitchenIndoor spacesWalkability

4.93 out of 5 average rating, 147 reviews