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Family-friendly vacation rentals in Castleton

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Castleton

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

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Guest favorite
The inviting living room features a modern wood-burning stove against a backdrop of light wooden walls. A comfortable dark sofa is arranged around a round wooden coffee table, complemented by a decorative plant. Natural light filters through the windows, enhancing the cozy atmosphere.
Cabin in Londonderry
4.95 out of 5 average rating, 248 reviews

Summit View Cottage:Ski | Hot tub|Fireplace3bd 2ba

Summit view cottage boasts 3 acres in the beautiful green mountains, we are 1,700 feet up in elevation . At this brand newly built PET FRIENDLY cabin you will have 3 bedrooms and 2 full bathrooms, which will sleep 7 comfortably. We have a brand new 6 person HOT TUB! You will find yourself within 15 minutes to the world famous Stratton mtn, 15 minutes from Bromley mtn and a close 4 minutes to the local Magic mtn.Very close proximity to the town of Manchester, which has great shops and restaurants

Guest favorite
An organized kitchen features white cabinetry with glass accents and decorative hardware. Stainless steel appliances, including double ovens and a gas stove, are highlighted. A countertop is prepared with utensils and a cutting board, while a textured backsplash adds subtle detail.
Home in Fair Haven
4.92 out of 5 average rating, 197 reviews

Historic 4 Bed 2 Bath Victorian Estate Fast Wifi

Ski season has begun! Take it easy at this unique and historic property. Picturesque Victorian Estate next to the Castleton River perfect for weddings and events. You can wake up with birds chirping and fall asleep to the frogs croaking. Church bells ring throughout the day while relaxing on the covered porch. Walk the historic slate sidewalk to the park and downtown for shopping and dining. Minutes to many lakes and trails. Day trips to Killington, Woodstock, Lake George, Vergennes, & Rutland.

Top guest favorite
An aerial view showcases a large, red two-story building with a metal roof nestled among lush greenery. The property features multiple decks and a private outdoor space. The surrounding landscape provides a serene backdrop of trees and grass, enhancing the natural setting.
Guest suite in Lake Bomoseen
4.97 out of 5 average rating, 249 reviews

My house is your house!

Relax in this refurbished quiet Lake view rental. Minutes from Lake Bomoseen/Crystal Beach. Large family room, Cast iron wood-stove. Wall of windows w/lake views. 65" 4K w/ surround sound. w/ game hook-up. Wi-Fi. Galley kitchen includes range, microwave, Keurig, fridge & wine cooler. Spacious bedroom, queen size bed w/ heated mattress pad. Lots of storage.Full bathroom. Private deck w/Adirondack chairs. Kayaks & boat launch. 15 miles to Rutland, 35 min to Pico & 47 min Killington Ski Resorts.

Top guest favorite
A vintage gas station building features a white exterior with red lettering spelling 'TEXACO.' Large glass windows line the front, showcasing a clear view of the interior. The American flag is displayed prominently, and a tree-lined background adds a touch of greenery.
Home in Castleton
4.94 out of 5 average rating, 150 reviews

Cozy Contemporary Downtown Texaco

Stay with us if you’d like to be in the center of downtown Castleton. Stores, restaurants, the college and hike/bike rail trail are an easy walk. This is a very convenient location. We are also a short 30-40 minute drive to Pico and Killington ski areas. Five minutes to Lake Bomoseen. Recently updated, heat and AC, full bath, Wi-Fi, Qled tv, a comfortable king sized memory foam bed, a complete kitchenette. Reserved parking adjacent to entry. Everything you need for an overnight or longer stay

Top guest favorite
Cabin in Clemons
4.99 out of 5 average rating, 114 reviews

Log Cabin Escape | Hot Tub + Mntn Views Near Lake

Welcome to the LOME! A one-of-a-kind log cabin nestled in the Southeast Adirondacks, between Lake Champlain & Lake George, with sweeping views of the Vermont Green Mountains. The hand-hewn beams overhead were salvaged from a 100-year-old family barn & every corner of this home has been crafted with love & intention. Whether you're here to hike, ski, spend lazy days by the lake, peep foliage, or genuinely unplug - this is the perfect retreat in one of the most beautiful spots in the Northeast

Top guest favorite
A unique treehouse is seen perched among tall trees, with a blend of rustic wood siding and large windows that reflect the surrounding greenery. The structure stands elevated from the ground, supported by slender pillars, blending harmoniously with the natural forest environment.
Treehouse in Hancock
4.98 out of 5 average rating, 170 reviews

Weasley's Enchanted Treehouse @ Vermont ReTREEt

Welcome to our enchanting treehouse! We crafted this unique and magic inspired dwelling for any admirer of a beloved wizarding world, or anyone who appreciates isolation in a fun space. As you cross the elevated walkways, you'll feel like you're entering a wizards treehome in the forest. The 1,100 sqft treehouse is nestled in and among trees, providing a magical and secluded escape from life. Have a question or hesitations? reach out check out our other listings for glamping style treehouses

Top guest favorite
A charming one-bedroom cabin is nestled among tall trees in a forested area. The wooden exterior is complemented by a porch with a railing and flower pots, creating a rustic appeal. Natural light filters through the windows, enhancing the cabin's tranquil setting.
Tiny home in Castleton
4.99 out of 5 average rating, 119 reviews

Cabin-by-the-falls

One-bedroom cabin (one double bed only) for those who want tranquility. Parking at main house and then short walk downhill, then level rocky trail to the cabin, which is located at a stream and waterfalls. There is a composting toilet, electricity and water. Wifi at main house, on deck, 5 mins walk. Wood burner in cabin, and propane stove in outside kitchen. A stand pipe (potable) or water from nearby stream (non-potable). There is a deck overlooking the stream with a picnic table.

Top guest favorite
A wooden deck offers seating with two lounge chairs, presenting expansive views of a field and distant mountains at sunset. The sky is painted in warm hues, while a solitary tree stands nearby, adding to the serene landscape.
Yurt in Pittsford
4.97 out of 5 average rating, 160 reviews

Remote Cozy Yurt with Sunset Views

Enjoy some time in a secluded yurt nestled in a quiet valley with spectacular sunset views. It comfortably sleeps 4, but can accommodate more. There is a bathhouse with an outdoor shower, compost toilet, and sink. Complete with propane stovetop, grill, and all necessary kitchenware. Stays in colder months will enjoy the warmth and comfort of a wood stove. Guests can also enjoy a small trail system on property for exercise or leisure. We hope you will come enjoy this peaceful retreat!

Top guest favorite
The cabin is nestled among tall trees, showcasing a stone chimney and wooden exterior. A stone walkway leads to the entrance, while a covered wood storage area is visible nearby. Bright green leaves provide a natural canopy, creating a serene atmosphere.
Cottage in Whitehall
4.99 out of 5 average rating, 236 reviews

Hillside Cottage @ The Mettawee Retreat

The Hillside Cottage is a luxury cabin with views of the Mettawee River. Located on 26 acres on a back road, it is peaceful & private. Enjoy fishing, swimming, kayaking or relax on the deck. This riverside retreat includes a king bed, jacuzzi tub & a kitchenette. Sitting around the fire pit with dinner cooked on the grill is the perfect ending to a long hike. Whether it’s a quick get-away or an extended vacation, the Hillside Cottage is a simple solution from a complicated life.

Top guest favorite
The Kingsley Grist Mill is positioned alongside a flowing river, surrounded by trees showcasing autumn colors. A historic covered bridge is visible in the distance, enhancing the landscape. The building features multiple stories with varying textures and roof styles, reflecting its rich history.
Castle in Clarendon
4.98 out of 5 average rating, 497 reviews

Kingsley Grist Mill Waterfall & Private Beach OMG

One of the "World's Most Amazing Vacation Rentals " as seen on the exciting NetFlix series, s.2, ep.7 and on HGTV's "You Live in What?, s.2, ep.1. Join us this season for the romance, the history, the breakfast, the natural mineral spring tap water, the concert, the rafting, the architecture and the legacy of the KGM, Vermont's Wright-esque falling water masterpiece. No cleaning fees added. Come make history with us ! Near Killington & Okemo Mtns.

Guest favorite
A serene view of a lake framed by abundant greenery, showcasing towering trees and gentle hills in the background. Various charming cabins line the shore, with blue water reflecting the clear sky above.
Cottage in Castleton
4.87 out of 5 average rating, 138 reviews

Family or couples retreat on Lake Bomoseen

Newly Renovated! 3 bedrooms 2 baths relax and take in the lake views on the multiple decks. Great for a small family or couples retreat. Boat slip and dock and 100 feet of frontage to enjoy. Bring your boat or kayak or rental. Fully stocked kitchen. Just Bring your SHEETS and TOWELS. Sunsets are great! Lake activities or hiking, biking, horseback riding, all close by. Close to Rutland and Skiing! No large parties or events

Top guest favorite
A small balcony features a blue bistro table with two matching chairs, accompanied by a vase of fresh flowers. Scenic views of rolling hills and lush greenery extend beyond the railing, while a wooden fence offers a sense of privacy.
Guest suite in Castleton
4.99 out of 5 average rating, 147 reviews

Vermont Hill Top Studio

You can see the stars from your Bed at Night - Studio space with a private entrance located on the quiet eastern end of our house. Twelve foot window provides spectacular views of Bird Mountain, & Killington, Pico Castleton is located in a great central location which acts as a great launching point for Lake Bomoseen , Killington / Pico Resort , or exploring the state

Popular amenities for Castleton family-friendly rentals

When is the best time to visit Castleton?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$84,116 GYDG$87,882 GYDG$72,817 GYDG$62,773 GYDG$81,187 GYDG$88,929 GYDG$71,352 GYDG$68,004 GYDG$75,328 GYDG$75,328 GYDG$75,328 GYDG$78,466 GYD
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Quick stats about vacation rentals that are family-friendly in Castleton

  • Total vacation rentals

    Explore 50 vacation rentals in Castleton

  • Nightly prices starting at

    Castleton vacation rentals start at G$20,924 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,390 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Castleton vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Castleton rentals

  • 4.8 Average rating

    Castleton stays are highly rated by guests—averaging 4.8 out of 5!

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