
Family-friendly vacation rentals in Charleston
Find and book unique family-friendly homes on Airbnb
Quick stats about vacation rentals that are family-friendly in Charleston

Total vacation rentals
Explore 40 vacation rentals in Charleston

Nightly prices starting at
Charleston vacation rentals start at G$16,729 GYD per night before taxes and fees

Verified guest reviews
Over 1,590 verified reviews to help you choose

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
40 of Charleston vacation rentals include wi-fi 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.

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.

Unique stay at a horse sanctuary
Immerse yourself in the quintessential Vermont experience at Storeybrook Farm. This rescue horse sanctuary is located amidst rolling hills, mountain vistas and a tranquil pond. "The Carriage House” is our largest suite with a fully equipped kitchen (stocked upon request), that opens up to a dining area with forest views. The living room features a woodburning fireplace and 2 built in queen bed "bunks". Enjoy sun-soaked pasture views from the main bedroom or while soaking in the clawfoot bathtub.

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.

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.

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.

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

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!

Entire place, newly renovated
Spacious apartement with large kitchen and equipped with all the cooking essentials. Private room with a double size bed. A futon is also in a separate room witch is not a bedroom 2 foldable beds available if needed. for a Total of 6 Close from Stanstead's main attractions : 5 min walk from the stone circle, the bazar and the famous Haskel library. 5 min ride from Canusa street, the beautiful Tomifobia bike path, restaurants, Pat Burn arena, the bakery and the grocery store.

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!

Mother in Law Guest Suite.
Take it easy at this unique and tranquil getaway. A home away from home. 1 Bedroom (Queen Bed), private Mother in Law Suite, Fully stocked with everything you need. Cute Coffee bar, Wi-Fi/Streaming Services. Direct access to snowmobile/ATV trails. Enjoy the outdoors by a toasty fire pit, beautiful sunsets, direct access to Lake Memphremagog’s far south end, fishing and canoeing. Only a short 3 mile drive to downtown Newport. Only 30 minutes from Jay Peak or Burke Mountain.

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.

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.
Popular amenities for Charleston family-friendly rentals
Family-friendly home rentals with a hot tub

Scandinavian chalet • Sauna spa • Quiet nature

The Caterpillar House: Tiny w/ Hot Tub & Fire Pit

Spring Hill Farm, coffee & hot tub

The Old School | Spa | Natural Park | Countryside

La Cabine Potton

HAVRE DE PAIX lac-Golf-Tennis-Ski Mont Owl's Head

Beautiful Log Cabin Getaway

Caboose Tiny Home | Hot Tub, Sauna, River & Views
Family- and pet-friendly home rentals

Dream Cabin in Vermont

200 acre Stowe area Bunkhouse.

Chalet Kalel

Cady’s Falls Cabin

Peaceful + Cozy Farmhouse Near Jay Peak + Sutton

Birch Tree Cabin! Pets Welcome!

The Lodge at Blackberry Hill

The Rustic Retreat at Twin Ponds
Family-friendly home rentals with a pool

Hatley House - Pool, Garden, Cycling

Mountain View Farmhouse w/ Orchard, Pool is Open!

Cozy Chalet at Jay Peak

Ski in Ski out - fantastic location on the trail

The House of the Setting Sun, Private Apartment

Theatre in the Woods - Stowe, VT

64J Stunning sunset, AC, Hot Tub! Pool/gym passes!

Cozy Lakeside 2 bedroom Condo and Heated Pool!
When is the best time to visit Charleston?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$40,987 GYD | G$41,824 GYD | G$37,641 GYD | G$30,322 GYD | G$40,360 GYD | G$41,614 GYD | G$38,269 GYD | G$40,360 GYD | G$36,596 GYD | G$41,824 GYD | G$39,732 GYD | G$41,824 GYD |
| Avg. temp | -8°C | -7°C | -1°C | 6°C | 13°C | 18°C | 20°C | 19°C | 15°C | 8°C | 2°C | -5°C |
Destinations to explore
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- Pet-friendly rentals Charleston
- Family-friendly rentals Orleans County
- Family-friendly rentals Vermont
- Family-friendly rentals United States
- Jay Peak Resort
- Owl's Head
- Mont Sutton Ski Resort
- Santa's Village
- Bolton Valley Resort
- Jay Peak
- Omni Mount Washington Resort
- Ski Bromont
- Stowe Mountain Resort
- Cannon Mountain Ski Resort
- Jay Peak Resort Golf Course
- Kingdom Trails
- Spa Bolton
- Pump House Indoor Waterpark
- Mont-Orford National Park
- Cold Hollow Cider Mill
- Elmore State Park
- Bleu Lavande
- Fairbanks Museum & Planetarium
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- Boyden Valley Winery & Spirits
- Green River Reservoir State Park
- Little River State Park





