Family-friendly holiday rentals in Charleston

Find and book unique family-friendly homes on Airbnb

Quick stats about holiday rentals that are family-friendly in Charleston

Total holiday rentals
Explore 40 holiday rentals in Charleston
Nightly prices starting at
Charleston holiday rentals start at £60 per night before taxes and fees
Verified guest reviews
Over 1,550 verified reviews to help you choose
Pet-friendly holiday rentals
Find 20 rentals that welcome pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
40 of Charleston holiday rentals include wifi access
Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Charleston rentals
4.9 Average rating
Charleston stays are highly rated by guests – averaging 4.9 out of 5!

Top-rated family-friendly rentals in Charleston

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

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Top guest favourite

The unique timber-framed home features a striking stone chimney and an attached silo. The surrounding landscape showcases vibrant fall foliage, complementing the rustic exterior. Pathways of smooth stones lead to an outdoor seating area, inviting moments of relaxation amidst nature.

Barn in Morristown

Stunning Barn & Silo retreat, on 300 private acres

This home is sure to amaze children and adults alike. Located 14 minutes from downtown Stowe, this one-of-a-kind property is nestled in the green mountains and set on 300 privately owned acres. The timber framed barn home is unique with character and craftsmanship. Additional bedrooms and bathrooms are located in an attached silo which is truly spectacular. Whether you visit in the summer, winter, or fall; this magical home will not disappoint. Built & run by a seventh generation Vermont family.

4.98 out of 5 average rating, 131 reviews

Top guest favourite

A modern treehouse features a warm wooden exterior, elevated on a platform among vibrant autumn foliage. Large glass windows provide a view into the inviting interior space. Steps and a small deck lead to seating arranged on the ground level, surrounded by natural scenery.

Treehouse in Newport

Secluded Luxury Treehouse - Hot Tub + Projector

Our treehouse is a haven of well-being, peace, and elegance. In our stunning modern treehouse we have brought relaxation to a whole new level. Surrounded amongst us is nothing but woods & wildlife. An experience not to be missed. Put your favorite movie on the projector, get Zen in the cozy sun room, jam out to music on the record player, or grab a towel, and head for the custom cedar hot tub. It is time to create core memories that will never be forgotten. Welcome to a little slice of heaven.

4.97 out of 5 average rating, 341 reviews

Top guest favourite

A wooden boat dock extends over calm waters, with a boat moored alongside. Lush green grass and vibrant orange flowers frame the scene, providing a natural border to the water's edge.

Cottage in Newport

Pristine Lake Location in Vermont

Our cottage is located on Lake Memphremagog, an international lake shared with Canada. Visit our nearby hobby farm/children’s museum. Kayak, bike or hike to stunning natural settings or take day trips to a variety of interesting destinations, including maple sugar shops, alpaca or dairy farms, golf courses, a ski resort with indoor waterpark; or cross the Canadian border a few miles away and explore Quebec. A boat dock is available for use at our cottage with an access ramp a 1/4 mile away.

4.9 out of 5 average rating, 195 reviews

Top guest favourite

The newly constructed cabin features large windows and a wraparound deck, surrounded by lush greenery. A shed is positioned nearby on the well-maintained lawn, providing additional storage. The sky above is filled with dynamic clouds, enhancing the tranquil outdoor setting.

Home in Burke

Trailside Home in East Burke

Our cozy home is newly constructed, well-appointed, and tastefully decorated, tucked in a private clearing with direct access to the Kingdom Trail network and VAST snowmobiling trails, minutes from Burke Mountain, and a short drive to Lake Willoughby. Just up the road from the village of East Burke, we are close to nearby amenities yet in a quiet hillside surrounded by nature, the perfect location for a weekend getaway, whether you are biking, skiing, hiking or exploring the Northeast Kingdom.

4.98 out of 5 average rating, 177 reviews

Guest favourite

A serene lake view is captured at dawn, with soft orange and purple hues reflected on the still water. A wooden dock extends into the lake, framed by silhouetted trees. Mist hovers above the water, contributing to the tranquil atmosphere.

Guest suite in Brighton

Vermont North East Kingdom Lakefront Hideaway

Soak up lake life as you bask in coffee and magic sunrises right outside your window. Right on the VAST trails, location is perfect for two to three snowmobiler’s or two couple’s by request. The lake only 40 feet away, nesting loons and moose, great fishing. Canoes and kayaks at the ready. This classic pine "camp" style apartment will be your ultimate hideaway in Vermont. Fully sanitized private apartment, Entire downstairs, private outside entrance. Gorgeous window sunrise lake views.

4.93 out of 5 average rating, 123 reviews

Top guest favourite

Aerial view of the vibrant Vermont landscape, showcasing rolling hills adorned with a diverse palette of fall foliage. The rustic barn sits among expansive fields, framed by trees displaying bright autumn colors, with distant mountains in the background under a partly cloudy sky.

Barn in Morristown

200 acre Stowe area Bunkhouse.

Hello and welcome to our Red Road Farm 'Bunkhouse' -- We're so happy to host you! Sitting on our 200 acre estate this authentic barn offers our guests a chance to relax in the beautiful rolling hills of Vermont. Access the vast majority of our historic Stowe area land -- from our apple orchards to our extensive walking paths in fields and woodland. We hope that you can experience such fun and quiet time in our cozy, western-style bunk room. Located only a 10 minute drive from downtown Stowe.

4.97 out of 5 average rating, 251 reviews

Top guest favourite

A wooden bench with a decorative wrought iron back is positioned in front of a sign reading 'The House of the Setting Sun.' Lush greenery surrounds the bench, and a small rabbit is situated nearby, creating a peaceful outdoor scene.

Flat in Newport

The House of the Setting Sun, Private Apartment

The House of the Setting Sun is a great place to rest, relax & re-energize. Located in a family friendly neighborhood, while still within walking distance to restaurants & close to downtown Newport. The apt has its own dedicated WiFi, easy for working remotely. Downstairs is a room with a ping pong/pool table. You will have your own deck, where you can sit & enjoy a cup of coffee to begin your day or unwind with a glass of wine as the sun sets. Hosts on site and ready to assist if needed.

4.99 out of 5 average rating, 286 reviews

Top guest favourite

A classic white farmhouse is set against a clear blue sky, surrounded by lush green grass and shrubs. A rustic wooden fence frames the foreground, while a silver barn is visible to the right, completing the rural landscape.

Home in Brownington

Davignon Farm, Northeast Kingdom, Brownington, VT

Located between Burke Mountain and Jay Peak three miles from Lake Willoughby provides activities year round. The light and views from this quintessential Vermont farmhouse will amaze you! The property extends into the woods beyond the fields and 263 acres await your exploration. Open kitchen, new bathrooms, den and living room provide spacious comfort in this rural setting. The perfect couples getaway with a great location to take advantage of all the Northeast Kingdom has to offer!

4.99 out of 5 average rating, 164 reviews

Top guest favourite

The tranquil Clyde River reflects the vibrant hues of autumn foliage along its banks, with tall grasses swaying gently. A charming house is nestled among the trees, showcasing a harmonious blend with the natural landscape under a clear blue sky.

Home in Charleston

Northeast Kingdom, VT Clyde River House

Clyde River Farm & Forest's secluded Northeast Kingdom river retreat, the Clyde River House provides stunning views, shoreline, numerous birds, including bald eagles, nesting osprey, blue herons, and a pair of loons. Canoes and kayaks available for your use. Hiking, biking, cross country, downhill skiing trails, and snowmobile trails are within a short hike or drive of the house. Check out the many seasons of the Clyde River House. There's sure to be a time for you to visit!

4.92 out of 5 average rating, 237 reviews

Top guest favourite

The exterior of the cottage is shown, featuring a spacious deck adorned with potted flower arrangements and outdoor seating. A woodpile is neatly stored beneath the deck, while the grassy lawn and clear blue sky create a serene atmosphere.

Home in Charleston

Scenic cottage Echo Lake, Charleston, Vermont!

This charming cottage is very quiet & private, with sweeping views of Echo Lake and Bald Mountain. Perfect for a romantic getaway or a small family vacation. Walk down to your own private beach on Echo Lake. The approximate 5.5 loop around Echo is great for walking and biking. It’s about 15-30 minute drive to area restaurants, shopping, hiking trails and scenic sites. Kingdom trails is 30 minutes. Bring your passports as Canada is just 20 minutes away.

4.98 out of 5 average rating, 123 reviews

Guest favourite

Yurt in Newport

Vermont Yurt Farm Stay | Vermont Glamping

Spacious 30-ft off-grid yurt (700 sq ft) on a Vermont farm with horses, goats & friendly dogs. Larger than most expect, with room to relax and unwind. Peaceful, private, and pet-friendly, with a short walk to the yurt for added seclusion. Guests love the cozy wood stove, thoughtful amenities, and clear night skies. Near Lake Willoughby, Burke Mountain & Jay Peak. No WiFi or strong cell service—ideal for unplugging, slowing down, and recharging.

4.96 out of 5 average rating, 143 reviews

Top guest favourite

A welcoming cabin is set against a backdrop of vibrant trees. The exterior features a green facade with wooden trim. A covered porch with two red chairs and pumpkins creates an inviting entryway. Two windows flank the door, allowing natural light to illuminate the interior.

Cabin in Brownington

Village Camping Cabin

Located in the heart of Brownington Village, and about 15 miles from the Canadian border, our property allows for easy access to many scenic locations. Enjoy all that Vermont's Northeast Kingdom has to offer including many beautiful lakes, hiking trails, bike paths, and ski areas. There are about a dozen homes in the village and you will hear traffic going by, including horses and buggies carrying our Amish neighbors.

4.99 out of 5 average rating, 162 reviews