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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 $103 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,590 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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Superhost
A cozy tiny house is positioned among lush greenery, with a natural stone pathway leading to its entrance. White Adirondack chairs are visible on the patio, surrounded by wildflowers and large rocks. Tall trees provide a backdrop, enhancing the tranquil outdoor setting.
Home in Brownington
4.82 out of 5 average rating, 134 reviews

NEK Base Camp and Retreat w/ Sauna

Nestled in a corner of Vermont's Northeast Kingdom, this basecamp with private sauna is the perfect place to relax after a day of activities. After an action packed day, treat yourself to a few cycles in our sauna Adventures are everywhere in the NEK. 100+ miles of mountain biking. Skiing at Jay Peak, Burke Mountain and Lake Willoughby Backcountry. 100s of miles of ATV and Snowmobile trails. You'll find classic Vermont adventures, not to mention Golf, fishing, and hiking you can embark on.

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
4.98 out of 5 average rating, 119 reviews

Scenic cottage Echo Lake, Charleston, Vermont!

This charming cottage is very quiet & private, with sweeping views of Echo Lake and surrounding mountains such as Bald and Wheeler. Perfect for a romantic getaway or a small family vacation. This winter the snow is as good as it gets. Cross country ski or snow shoe here or at the many trails nearby. Or just walk out onto the lake and smile. Message for conditions Bring your passports as Canada is just 20 minutes away with great food shopping and restaurants and scenic spots.. It is beautiful.

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
4.97 out of 5 average rating, 317 reviews

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.

Top guest favourite
A tranquil view of Lake Memphremagog is presented from the deck. The expansive water stretches toward the horizon, framed by a clear blue sky. A grassy area and a single tree are visible in the foreground, enhancing the serene lakeside setting.
Apartment in Newport
4.97 out of 5 average rating, 101 reviews

Cozy Lakeside Condo and Heated Pool! 10% off week

SUMMER MINI BREAKS WELCOME! Welcome to our cozy two-bedroom condo featuring stunning views of Lake Memphremagog with a private balcony. Enjoy access to the lake and heated pool, open from Memorial Day through Labor Day. This first-floor (upper-level) condo offers two bedrooms and two bathrooms, along with a comfortable living space. The open-concept kitchen and dining area flow into a bright, inviting living room, complete with baseboard heating. PLEASE NOTE: There is NO AC in the summer.

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
4.99 out of 5 average rating, 265 reviews

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.

Top guest favourite
A rustic kitchenette features wooden shelves stocked with dishes and utensils. A small sink and countertop are complemented by a compact refrigerator and a single burner induction cooktop. Light wooden walls and a doorway leading to the bathroom create a cozy, natural atmosphere.
Guest house in Burke
4.97 out of 5 average rating, 119 reviews

Farm Stay in Burke at Firefly Farm

By staying at Firefly Farm in the Northeast Kingdom, you get to experience a connection with the earth, be part of the community and ride the trails. Our guest house is small (120 sq ft), cozy, and the perfect place to set up base for exploring. Though small in size, the space includes a table that converts into a bed, a bed above the table, a kitchenette, and a bathroom with a full sized shower. Stay with us and enjoy the beauty of the Northeast Kingdom! We do not charge any cleaning fees.

Top guest favourite
The red wooden house features a welcoming entryway with a prominent front door framed by large windows. Bright green foliage lines the path, enhancing the natural setting. The garage is visible on the left, with sunlight illuminating the exterior.
Home in Hyde Park
4.97 out of 5 average rating, 295 reviews

CLASSIC VT STYLE

This is an authentic VT house tucked between two of the state's most celebrated ski resorts, Stowe and Smuggler's Notch. We are about 30 minutes north of Mount Mansfield with tons of hiking and exploration opportunities. In this area you can enjoy some of the state's most popular outdoor recreational attractions and activities. The space is private and serene and works for all different kinds of local adventures in any season. Come experience a unique part of VT in your own unique VT home!

Top guest favourite
A cozy cabin exterior, constructed from logs, is set against a backdrop of snow-covered trees. A front porch is accessed by a set of stairs, and seasonal decorations, including a snowman and a gingerbread figure, add a cheerful touch.
Cabin in Brownington
4.96 out of 5 average rating, 142 reviews

By Lake-Westmore-Hike-Ski-Lots to do. Cabin 3-View

Four seasons cabin you can just walk into with just your bags. Cozy and comfortable located near lakes, golf, hiking trails, winter skiiing. 2 Adults,2 kids. Extra ADULTS $20.00 each per night You will find so much to do in the NEK!.Bedroom downstairs and bedroom up in the loft with 2 double beds. Info in cabin in cabin full of places to go and see and enjoy. Recently built. *Please note the minimum booking is for 3 days. Maximum is 7 days.*** Please leave cabin as clean as found. Cabin#3

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
4.99 out of 5 average rating, 157 reviews

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!

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
4.92 out of 5 average rating, 235 reviews

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!

Top guest favourite
A modern living area features a comfortable brown sofa beside a wooden coffee table. Exposed wooden beams run across the ceiling, while a staircase leads to an upper level. Natural light fills the space through large windows, creating a warm and inviting environment.
Cabin in Montgomery
4.94 out of 5 average rating, 176 reviews

Jay Peak Retreat

The Jay Peak Retreat – Experience the Northeast Kingdom’s premier destination at Jay Resort, known for record snowfall and Vermont’s largest indoor waterpark. This warm, stylish cabin offers an open-concept layout perfect for cozy gatherings and après-ski lounging. Blending upscale comfort with rustic charm, enjoy a creek out back, river across the street, patio, fire pit, and plush outdoor chairs. Just 1 hour from Burlington, 2 from Montreal, 35 minutes to Sutton Quebec!!

Guest favourite
The exterior of a spacious blue yurt features a wooden entrance deck with a decorative door. Surrounding greenery enhances the natural setting. A chimney is visible, indicating a wood stove inside, while a hammock is positioned nearby, inviting relaxation.
Yurt in Newport
4.96 out of 5 average rating, 138 reviews

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.

Popular amenities for Charleston family-friendly rentals

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