Family-friendly vacation rentals in Bolton

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Bolton

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

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Guest favorite

A cozy log cabin is nestled among lush greenery, featuring a wooden deck with steps leading up to the entrance. Large windows provide ample natural light, and the surrounding trees contribute to the tranquil setting.

Cabin in Richmond

4.94 out of 5 average rating, 181 reviews

Log cabin in the woods in Richmond VT (near Stowe)

Informal, cozy, comfortable log cabin on 25 acres of land with a babbling brook. Tucked away on a very well-maintained country road. Perfect for a VT getaway, we are close to incredible year round activities of skiing, hiking, and biking. With easy access to I-89, Route 2, & Route 100, we are 10 minutes from Bolton Valley, 45 minutes from Stowe, and 20 minutes from Burlington. Many restaurants & stores are within a 15 minute drive. The perfect cabin for friends or family to enjoy a VT vacation.

Guest favorite

A round yurt is surrounded by lush green trees, with a tan conical roof and large windows that invite natural light. The pathway leading to the entrance is bordered by various plants and shrubs, enhancing the connection to the natural setting.

Yurt in Bristol

4.93 out of 5 average rating, 317 reviews

Bristol Cozy Yurt near Hiking/Swimming|MapleFarm

Our cozy yurt is located within minutes of amazing, hiking, biking, skiing, breweries and much more! Relax around the fire while listening to our resident owls or stare up at the stars through the dome. We're centrally located to some of the best hiking and swimming skiing in Central Vermont. Mt Abe and Bartlett's Falls are the closest options. We're also close to civilization with several towns close by to explore for food, drink, art, and shopping. Or travel a bit further to Burlington..

Top guest favorite

A lush, green landscape is framed by trees and gently sloping hills. The manicured lawn leads to a quaint white home in the distance, surrounded by vibrant foliage under a partly cloudy sky.

Guesthouse in Corinth

5 out of 5 average rating, 146 reviews

The Guest House at Chandlery Farm

This classic Vermont farm estate has everything that description implies: end-of-the-road privacy with breathtaking views, where the only sound is the wind rustling through the leaves. The manicured gardens, stone walls and quaint but luxurious home seem plucked from classic American folklore. Guests can drink their morning coffee while soaking in views of rolling pastures and forested hills, and spend their days exploring the property's trails, and the beautiful towns and countryside nearby.

Guest favorite

A spacious living area features large windows framing mountain views and a cozy fireplace. Natural wood accents complement the soft furnishings, including a circular glass coffee table atop a patterned area rug. A dining table for two is positioned near the sliding doors leading to the outdoor deck.

Home in Moretown

4.98 out of 5 average rating, 286 reviews

Dramatic Views at the Above the Clouds Guesthouse

As featured in Conde Nast Traveler (1/21/22) Peaceful & impeccable retreat with a 180 degree view of Vermont's tallest mountains. Near Vermont's premier skiing, hiking, & outdoor adventures, you’ll love the sunset views and cozy atmosphere (huge sheepskin in front of the fireplace) and the attention to detail (live-edge wood details, spa-like bathroom). This is an incredible retreat for couples and families, adventurers and business travelers alike! COMPLETE COVID-19 CLEANING

Top guest favorite

A tiny house features a wooden exterior with a light-colored door framed by large windows. A small porch with two chairs and a table provides an inviting entrance, while additional seating is arranged on a grassy area, surrounded by trees and natural greenery.

Tiny home in Duxbury

4.97 out of 5 average rating, 280 reviews

Tiny House at Camp Comyns

NO check in. Total privacy. Tiny House with a big heart! This magical place is located 3 miles from Waterbury (I-89 exit 10), walking distance to Camel's Hump hiking trails and the Long Trail. Cross Vermont biking, VAST snow mobile trails, kayaking, swimming, fishing, skiing and more. Breathtaking views of mountains, gorgeous foliage. Great restaurants, breweries and live music all within five miles. Plenty of parking. Close to Stowe, Montpelier, and Burlington.

Guest favorite

A spacious living area features a large arched window allowing natural light to fill the room. A wooden coffee table is centered on the floor, while a small desk and chair sit nearby. Potted plants add a touch of greenery, complementing the earthy tones of the walls.

Apartment in Waterbury Center

4.91 out of 5 average rating, 212 reviews

B suite Zenbarn 2BR Apt | VIP Perks Live Music

Zenbarn Loft: A Cozy 2-Bedroom Retreat Above Vermont’s Iconic Music Venue 🎶⛰️🍻 Stay in the heart of Vermont, just minutes from Stowe, Waterbury, and top breweries like Alchemist and Lawson’s! This 2-bedroom suite offers a cozy retreat with a kitchenette, fast WiFi, and a private entrance (shared hallway). Live music below creates a vibrant atmosphere. Please message us before booking with any questions to ensure this is the perfect stay for you!

Guest favorite

A cozy sitting area features a couch and an armchair, complemented by decorative cushions. Wall art is displayed above a television, and a kitchenette is visible in the background. Warm lighting enhances the inviting atmosphere in this thoughtfully arranged space.

Guest suite in Waterbury Center

4.93 out of 5 average rating, 456 reviews

Waterbury Center Guest Bedroom - 244 Howard

The guestroom room is very cozy with radiant heat in the floor during the winter. The separate entrance is off a covered porch. The porch has chairs and a table and is very pleasant in the warmer months The little kitchen alcove is convenient for coffee or tea or a light meal. We live in a historic building and our neighborhood is located very close to Rte 100. Waterbury village and Stowe as well as skiing, hiking and biking are all nearby.

Guest favorite

The living area showcases comfortable seating arrangements with two sofas and an armchair. A wood stove is positioned between the seating and a coffee table. Large windows allow for natural light, complemented by simple wooden dining furniture in the background.

Cabin in Huntington

4.96 out of 5 average rating, 147 reviews

The Sled at Fielder Farm

The road to the Sled at Fielder Farm gently winds its way out of the Huntington Valley and into the foothills on the western side of Camel's Hump. The road follows and crosses one of the many mountain brooks swelling the Hunting River as it rushes for the Huntington Gorge downstream. Regardless of the season, the diverse landscape occupied by Fielder Farm offers visitors a variety of activities right out the front door.

Top guest favorite

The cottage is nestled among lush greenery, showcasing a modern design with a metal roof. A welcoming porch extends along the front, framed by tall trees, while a stone pathway leads to the entrance. Natural light is abundant, highlighting the serene outdoor setting.

Cottage in Stowe

4.98 out of 5 average rating, 115 reviews

Cottage at Strawberry Hill Farm

The Space This exquisite one-bedroom cottage is located on the grounds of a 200 acre estate in the center of Stowe. The cottage is at the far end of a quiet, peaceful meadow and looks out onto a spring-fed pond with views of Mt. Mansfield. There are countless walking/running/biking/XC trails both on and adjacent to the property. The trails on the property connect to the very popular Cady Hill mountain bike network.

Top guest favorite

A rustic barn features a combination of wood siding and a dark metal roof, set against a clear blue sky. The structure includes multiple windows and a peaked section at the top. A porch with chairs is visible in the foreground, surrounded by well-maintained grass.

Guest suite in Hinesburg

4.97 out of 5 average rating, 1,280 reviews

Boston Magazine Pick! Barn Loft

*** Chosen by Boston Magazine as one of five New England barns to rent! *** Our beautiful barn loft in Hinesburg is close to Burlington, the Green Mountains and Lake Champlain. It features a new kitchen, cathedral ceilings, plenty of natural light, rustic charm and lovely views. The space has its own entrance and is completely separate and private from the main house.

Guest favorite

A lush green landscape is visible, featuring a serene riverbed bordered by trees. Several sheep graze peacefully on the grassy area, with gentle hills and distant mountains in the background under a partly cloudy sky.

Farm stay in Stowe

4.93 out of 5 average rating, 101 reviews

Riverbed Farmstead - Hayloft (sleeps 2-4)

Forget your worries in this spacious and serene space. Beautiful location in Stowe on the Little River with views of Mt. Mansfield (Stowe Resort). This spacious unit has one bedroom and one bath with a large open kitchen/living/dining space. Freshly painted and well appointed with a mix of modern and antique furnishings. Second floor - full kitchen.

Top guest favorite

An open living area showcases a comfortable seating arrangement with a dark leather couch and armchair. A wooden table with decorative accents is positioned in the foreground, accompanied by a lamp. Large windows allow natural light to fill the space, complemented by a ceiling fan.

Guesthouse in Stowe

4.98 out of 5 average rating, 281 reviews

Sunny, Quiet and Close To Everything

Come visit Stowe in any season! We live on a dead-end dirt road that is close to town and to the mountains. There are trails right from the house that connect to the Cady Hill trail network and skiing, snowboarding, hiking, music, swimming holes and more just minutes away. Come visit!