Family-friendly holiday rentals in Charleston

Find and book unique family-friendly homes on Airbnb

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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Guest favourite

Cabin in Stowe

4.93 out of 5 average rating, 354 reviews

The Rabbit Hole - Luxury Cabin in heart of Stowe

Located in the heart of Stowe. Close to everything Stowe has to offer, yet set back enough for that mountain getaway feel. 3 miles from Stowe Mountain Resort, 1.5 miles to Alchemist brewery, restaurants/shops/farmers market etc. Walk to Stowehof resort, Weisner Woods hiking trails and popular rec path. Beautifully furnished, hot tub, amazing beds, fast wifi, two 50" TV's, sound system, smart lighting, etc. Relax in the hot tub, the bohemian outdoor living space and or next to the peaceful pond.

Superhost

Home in Belvidere

4.93 out of 5 average rating, 162 reviews

Cozy Adams Farmhouse - Spring Availability!

Welcome to the Adams Farmhouse, your dream ski weekend retreat in the heart of Vermont! Nestled just a short drive away from Jay Peak, Smuggler’s Notch, and Stowe Mountain Resort, our charming farmhouse is the ideal base for your winter adventure. Wake up to breathtaking mountain views and spend your day conquering the slopes. After an exhilarating day of skiing or snowboarding, come back to a warm, welcoming home. Book now and create unforgettable memories in Vermont’s winter wonderland!

Guest favourite

Cottage in Whitefield

4.96 out of 5 average rating, 239 reviews

Private Pond Escape: Luxe Cottage/Private Isle

Luxurious Cottage on pristine private pond with outdoor wood fireplace and gas fire table. Cross graceful bridges to your Private Island with screened gazebo. Perfect getaway! Have coffee or cocktails on the deck with mountain and lake view or hike the trails on our 68 acres to the Gold Mine Trail. With a full kitchen, fine china, new shower, Jacuzzi bathtub, electric fireplaces, and two workspaces, this dog-friendly luxury cottage has it all! Make memories in this charming retreat!

Guest favourite

Cabin in Barton

4.81 out of 5 average rating, 159 reviews

Charming lake cottage on Crystal Lake! Boats! R&R!

Lakeview Cottage is adorable and located on one of Vermont's cleanest and most beautiful lakes, Crystal Lake! It's in the heart of the Northeast Kingdom, in the charming town of Barton. Sit around the outdoor firepit and soak in the view! You're just steps away from beaches and a dock. You'll find great swimming, fishing, boating, hiking, golfing, and mountain biking. Use our canoe or kayaks! Plus, Hill Farmstead Brewery is a short drive away. Beers there are rated best in the world!

Top guest favourite

Cabin in Hyde Park

4.96 out of 5 average rating, 278 reviews

Serene Country Cabins 2 In the heart of Vermont

My place is close to Stowe, Smuggler's Notch and within 15 minutes of 6 breweries. It is nestled in the woods with some views, art and culture, farms, hiking trails, lakes, 3 major ski resorts, snow machine trails, and 3 miles from the down town shopping plazas. My place is good for couples, solo adventurers, business travelers, families (with kids), and furry friends (pets). Our bedrooms offer a create a king to accommodate guests who prefer a king bed and guests who prefer twin beds.

Guest favourite

Home in Lyndon

4.94 out of 5 average rating, 182 reviews

Scenic VT Vacation Home: Kingdom Trails/Burke Mtn

Bike the Kingdom Trails, ski Burke Mountain, Jay Peak, hike our woodlands and enjoy spectacular stargazing from one of the loveliest panoramic views in Vermont’s Northeast Kingdom. Our beautiful uniquely designed four-bedroom, 8 beds, two full bath vacation home includes 37 acres with spectacular, stunning views of Burke Mountain and the Kirby Mountain Range. This spacious vacation home is a quintessential Vermont gem with breathtaking mountain and valley views from every room.

Guest favourite

Townhouse in Stowe

4.89 out of 5 average rating, 167 reviews

Stowe, Topnotch Resort-Best Mt & Luxury in Vermont

This beautiful Resort Condo is located in the award-winning, Top Notch Resort & Spa. Our spacious 2-bedroom, 2-bathroom condo is only 1 mile away from Stowe Mt. Resort while offering privacy and room to spread out on the resort’s 120 acres. It is perfect for families or couples. We are proud of our stellar reviews and competitive pricing. Newly updated, our home is ready for your perfect vacation! Enhanced Cleaning protocols in place!

Guest favourite

Home in Stowe

4.98 out of 5 average rating, 159 reviews

Spacious Eco-Friendly Stowe Home for Family Fun

Vacation/Work Remotely or both in this 5 BR and 5 BA gorgeous mountain eco-friendly home. FIBER 100 meg symmetrical wifi, a quiet workspace with desk, monitor, and printer. Fully stocked kitchen, ping pong, fire pit, large family space but quiet spaces too, and 3 ensuite bedrooms! Conveniently located close to town and a short drive to skiing. This is a great family space to reconnect or a space to work remotely for a change of pace.

Superhost

Home in Stowe

4.83 out of 5 average rating, 161 reviews

Great For Large Groups with Hot Tub

This property is not suited to noisy groups - please don’t book for partying. Recently renovated to meet every vacation need, this unique property has everything you require for a great trip. The property is huge, ideally located right on Mountain Rd - minutes to slopes, spas, breweries, restaurants, hiking, biking and swimming holes. With 4 large comfortable bedrooms, fun basement, huge living space with fireplace and private hot tub.

Guest favourite

Cabin in Cabot

4.94 out of 5 average rating, 216 reviews

Cabot Cabin on a Road Less Traveled

Our cozy 1830's cabin right down the road from a famous breathtaking view over the Northeast Kingdom. Our cabin is undeniably rustic but furnished with well-loved antiques. Open floor plan - bebdrooms open to house. DSL wifi /smart TV. Natural landscape, right on a well-maintained dirt road not far from the main road & Cabot Village. Note: no pets, children 7yrs and up only.

Superhost

Home in Bethlehem

4.81 out of 5 average rating, 170 reviews

The Craftsman Farmhouse with Modern Flair

Take in the best of mountain living while staying a in a craftsman-styled farmhouse, a short walk from an historic resort town’s main street. Your accommodations will be in an architect’s dream: a 1930 Craftsman era home with architectural details with retro-modern furnishings and artwork—exhibiting true attention to craft & detail.

Top guest favourite

Flat in Cambridge

4.94 out of 5 average rating, 103 reviews

Smugglers' Notch, VT

The condo is part of Smugglers Notch Resort. The condo is in an excellent location - a three minute walk to the Village Center and the Village Ski Lift. Hiking and outdoor adventure a short walk away. The unit is an updated 2 bedroom, 2 bath condo with full kitchen, dining and living room areas.