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Family-friendly holiday rentals in Charleston

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Charleston family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Cabin in Stowe
4.92 out of 5 average rating, 357 reviews

The Rabbit Hole - Luxury Cabin in heart of Stowe

SuzanneRating, 5 stars1 month ago
The house was perfect for us. We were a group of 8 and everyone had a comfortable place to sleep, plenty of space to move around, park our cars and sit while relaxing throughout the house. Ryan was so helpful and quick to respond if we had any questions. Lovely house, hope I get to return.
Guest favourite
Chalet in Knowlton
4.88 out of 5 average rating, 109 reviews

Smart Chalet pour grande famille et gens sportifs

LeylaRating, 5 stars1 week ago
Great spot for groups, plenty of space, host was very flexible with check in and out and easy to reach
Top guest favourite
Chalet in Mansonville
4.99 out of 5 average rating, 118 reviews

Chalet HAVRE DE PAIX sur pistes Mont Owl's Head

SteveRating, 5 stars3 months ago
Bel endroit, idéal pour le ski. Bien équipé. Nous avons apprécié descendre en luge les pentes une fois la station fermée.
Guest favourite
Home in Stowe
4.94 out of 5 average rating, 189 reviews

Huge deck, hot tub, foosball, surrounded by nature

MaritaRating, 5 stars2 months ago
Great stay at Jen’s beautiful chalet. Easy to communicate with and well equipped with many kitchen supplies and all the needed towels, linens, hairdryers, and a thoughtful welcome package. Only about 15 mins from the mountain and 10 mins to town. Thanks!
Guest favourite
Cabin in Danville
4.96 out of 5 average rating, 119 reviews

Beautiful Log Cabin Getaway

StephanieRating, 5 stars3 months ago
We had a lovely and relaxing stay. The cabin and surrounding property are beautiful, and Evangelyn was a wonderful host. If you’re looking for a peaceful, “home away from home” getaway, this is just the place.
Guest favourite
Home in Waterbury Center
4.95 out of 5 average rating, 132 reviews

Peaceful setting with Mountain Views

HallieRating, 5 stars4 months ago
Home away from home! Susan was a fantastic host. She was very responsive and communicated quickly. This home was perfect for our group of 6 and it was extremely cozy! This was our first time in Vermont and it definitely exceeded all of our expectations. If you looking for a pleasant place to stay with amazing views, look no further than this adorable Airbnb! We skied in Stowe, toured the Ben and Jerry’s ice cream factory down the road and enjoyed some live music at the ZenBarn. I would highly recommend this property! We hope to visit again soon :)
Guest favourite
Chalet in Hatley
4.85 out of 5 average rating, 121 reviews

Blue cottage near the lac, spa, fire place

JenniferRating, 5 stars2 months ago
We had a wonderful visit in the Eastern Townships and it was great to stay here. We appreciate everything!
Superhost
Chalet in Sutton
4.82 out of 5 average rating, 189 reviews

Chalet Chïc Shack

FrancineRating, 5 stars3 weeks ago
Maxime was so nice and very quick to reply when we had a question. I was not expecting neighbours so close to the patio and the spa so there was not a lot of privacy when we were sitting outside.

Family- and pet-friendly home rentals

Guest favourite
Cottage in Lyndonville
4.9 out of 5 average rating, 299 reviews

Your Own Perfect Little Cottage

AnneRating, 5 stars1 week ago
Wow! What a beautiful setting & views!!! Creative sculptures and art ! Super comfy bed for us! Friendly for pets! If only I had been there longer , would have definitely worked on painting… very inspirational setting for artwork! Took lots of photos and we enjoyed seeing the art, architecture, Carolina poplar trees , grape honeysuckle, peony, and tiny pink lilacs!Hope to stay again in any season! Kitchen bits had everything we needed for a short stay. We had an additional cooler as well, that we brought which helped. Nice hot shower too! Small bathroom next to pantry very functional but no privacy as open to pantry. Gotta be very comfy and not shy with whomever you might be sharing space with 😉. No worry for us but others might want to be aware. Truly enjoyed overall!
Guest favourite
Cabin in Hyde Park
4.94 out of 5 average rating, 589 reviews

Dream Cabin in Vermont

RebeccaRating, 5 stars1 week ago
We absolutely adored our stay at the cabin. It is idyllic inside and out! It was amazing to come home to after a day of exploring. The bed was super comfortable and the highlight for us was watching VHS on the TV with snacks. It is so well equipped and cosy, also enjoyed a lovely bath in the claw foot tub. Just perfect for a rustic, cosy stay in nature. A highlight for me was stepping outside at night and listening to (I assume they were) frogs!! They were so loud and it was incredible to hear them, the trees were also surrounded by fireflies (I’d never seen them before!) and I’ll always remember that perfect moment of peace. Thank you for making our 10 year anniversary so memorable with such a lovely place to stay, if you’re thinking of it for a special occasion or just as a base to explore this adorable region of Vermont, look no further :) thank you!
Guest favourite
Cabin in Lowell
4.88 out of 5 average rating, 250 reviews

Owls Head

BethanyRating, 5 stars2 months ago
My boyfriend and I stayed at the Owl's Head Cabin for a long weekend skiing at Jay. The cabin is small and cozy, very warm, and the right size for two people for a weekend. In addition to the main bed, there's a loft with a sleeping area, but you'd have to be very small to get into it and enjoy it; I'd guess the cabin would be a bit small for a couple with children but maybe if you're out all day it'd be okay. Cooking appliances worked well. The one note of caution is that you have to drive on a somewhat rough, uphill dirt road for at least 3 or 4 miles to reach the cabin. We fortunately did not have to drive during a time when there was actively snow falling on the road, but the 2wd sedan we rented definitely would not have made it in those conditions; it was a little harrowing even with just the slush and ruts left after plowing. So be careful if your trip coincides with nastier weather! Jason was very communicative and left clear instructions. Overall, we had a lovely stay.
Guest favourite
Home in Montgomery
4.95 out of 5 average rating, 129 reviews

Hillwest Mountain View

MelissaRating, 5 stars7 months ago
We had a lovely time at this quaint mountainous home. The neighbor nearby had some horses that grazed near the home every morning and the vistas in the distance were incredible to see. We would love to come back again next year, maybe during the more peak foliage season. Thank you all so much for your hospitality, especially for providing us an extra night!
Top guest favourite
Cabin in Burke
4.99 out of 5 average rating, 317 reviews

Razzle's Cabin trailside

Mattie RoseRating, 5 stars2 weeks ago
Sandy’s spot is a wonderful place to stay and experience the beautiful countryside of Burke VT. The home has everything you need from kitchen supplies to cozy blankets, we had such a sweet welcoming stay.
Guest favourite
Cabin in Hyde Park
4.95 out of 5 average rating, 355 reviews

Serene Country Cabins 1 In the heart of Vermont

JeffreyRating, 5 stars5 days ago
Another great stay! Hauss are wonderful and always communicating well. The cabin is clean, cozy, everything we need. The area is quiet and serene. We will definitely do over!
Superhost
Cabin in Morristown
4.9 out of 5 average rating, 250 reviews

Dream Log Cabins! Pets Welcome!

AngeloRating, 5 stars2 weeks ago
Claudia's place was EXACTLY what we were looking for on our VT getaway. Close to Stowe and Morristown, yet outside the madness of being in town. Claudia was the perfect host......accommodative, Fast response to messages, friendly and helpful. Despite other cabins on the property, this place was very private. Mr Charlie loved the fenced in yard to run loose in and the deck was perfect for sitting and relaxing. Would definitely consider this space again on our next trip to VT.
Top guest favourite
Chalet in Barnston-Ouest
4.91 out of 5 average rating, 380 reviews

House&loft near 5 lakes, pool table, fireplace, AC

MartineRating, 5 stars1 week ago
Superbe endroit très beau et confortable une des plus belles place que j’ai vue !

Family-friendly home rentals with a pool

Superhost
Apartment in Stowe
4.79 out of 5 average rating, 137 reviews

Luxury 1 Bedroom at Topnotch Resort!

ChrisRating, 5 stars4 months ago
Our family had a great time at the Topnotch Resorts. The unit was cozy and clean with everything we needed. It was great to have access to a washer and dryer to throw in the ski clothes from the day. The indoor pool and hot tub facility was beautiful with fresh towels available and and a family changing area. The outdoor pool and hot tub were also awesome with a view of the mountains in the background. Kelly at the front desk was a complete pleasure to work with. She answered all of our questions promptly and went above and beyond to help us and made sure our stay was amazing. We will be back!
Superhost
Flat in Magog
4.78 out of 5 average rating, 341 reviews

Magog studio - Waterfront - Cozy and confortable

Eros GonçalvesRating, 5 stars1 week ago
Super séjour! Le logement était propre, confortable et idéalement situé pour notre activité dans les environs. Je recommande sans hésiter cet endroit!
Superhost
Apartment in Stowe
4.81 out of 5 average rating, 284 reviews

Spacious Stowe condo Amzing views w/shared hot tub

JeffRating, 5 stars2 months ago
great place close to Stowe.
Guest favourite
Apartment in Orford
4.85 out of 5 average rating, 188 reviews

Cozyluxe! Condo chic et chaleureux avec spas!

JackRating, 5 stars1 month ago
A very good spot close to the mountain. A cute bar across the road, and the hot tubs were a great way to close the day.
Guest favourite
Apartment in Jay
4.91 out of 5 average rating, 162 reviews

Ski in Ski out - fantastic location on the trail

PatrickRating, 5 stars2 months ago
Just awesome. Slopeside access, close to Tram Side and right on Grammy Jay which was easy for the littles to get the day started on the way to the double. When it was cold (once) we used the fireplace and the condo warms up quickly. Plenty of hot water. A near perfect stay. Fantastic!
Top guest favourite
Townhouse in Stowe
4.87 out of 5 average rating, 214 reviews

Gorgeous panoramic views - 4 miles to the mountain

RuthRating, 5 stars2 months ago
Absolutely wonderful stay! As a family of five, we couldn't have asked for a better place. The unit was incredibly spacious, comfortable, and had such a warm, homey feel—it truly felt like a home away from home. The mountain view from the living room window was beautiful, a perfect backdrop for our mornings and evenings. Jeff, the host was exceptional—extremely responsive, thoughtful, and helpful throughout our stay. Every question or request was handled quickly and kindly, which made our experience stress-free and enjoyable. We had some wifi issues which took time to resolve but Jeff helped and made sure it is taken care of. The apartment was impressively well-equipped with everything we needed, clearly a lot of care went into preparing the space for guests. The location was perfect for us— surrounded by beautiful trails that we explored as a family. If you are into skiing, the ski tracks are short drive away. It was the ideal base for both adventure and relaxation. Highly recommended
Top guest favourite
Home in Stowe
4.98 out of 5 average rating, 267 reviews

EPIC Stowe Getaway - Great For Families & Friends

KatieRating, 5 stars2 weeks ago
weekend family trip for 6 of us and our dog(4 adults and 2 kids), plenty of space for everyone, and much larger than I expected! we enjoyed cooking in the well stocked kitchen, playing board games on the large dining room table, swimming in the pool and soaking in the hot tub, wrapping the nights up with a movie on their Roku TV! Kristin was very responsive in her communication, we had a lovely time and would love to plan future trips here again!
Superhost
Cottage in Stowe
4.77 out of 5 average rating, 241 reviews

Cute Cottage - Poolside - Minutes To Activities

ChrisRating, 5 stars2 months ago
Linda was a fantastic host, and her home was even better than listed. The cabin was a good size for our family of four + dog; the 2 bed / 2 bath arrangement allowed for good privacy when needed. The fireplace was great for apres and winding down at night. Location is a nice mix of seclusion (off the Mountain Rd), but close to everything.

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

  • Total rentals

    40 properties

  • Nightly prices starting at

    ₹2,597 before taxes and fees

  • Total number of reviews

    1.4K reviews

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    40 properties include access to wifi

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