Family-friendly holiday rentals in Bolton

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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 favourite

Guesthouse in Waterbury

5 out of 5 average rating, 222 reviews

Bright & Airy Guest House Downtown Waterbury

This meticulously cared for loft is very private, spacious, has an open layout, and is a second floor apartment that is full of natural light and unique, original artwork. Enjoy river views across a spanning lawn, and a willow tree allée to wander through all while charging your EV with our Level 2 charger! Want to see fireflies at night in the summer or get lost in a sea of stars at night? This property is a perfect mix of privacy and space while being in the heart of the downtown Waterbury VT.

Top Guest favourite

Cabin in Richmond

4.94 out of 5 average rating, 179 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 favourite

Yurt in Bristol

4.93 out of 5 average rating, 311 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 favourite

Bungalow in Worcester

4.97 out of 5 average rating, 671 reviews

Beautiful 30ft Yurt in the Green Mountains!

Gorgeous 5 STAR 30-ft yurt. The wrap-around deck looks out to the Worcester Range, trails leading from the yurt to babbling brooks. This charming space includes a fully equipped kitchen and a private bathroom with a claw foot tub/shower. Two queen beds, air mattress & futon mattress. 12 mi. to Montpelier and 7 mi. in the opposite direction to Lake Elmore, 4 miles to Worcester Trailhead and 6 miles to Hunger Mt! A beautiful sanctuary for peace and quiet or Netflix and Wifi, your hearts desire!

Top Guest favourite

Apartment in Waterbury

4.97 out of 5 average rating, 165 reviews

Lovely one-bedroom apartment

The apartment is centrally located - 5 minutes from Ben & Jerry's and Waterbury Village; 20 minutes from Stowe with great biking and hiking and 30 minutes from Burlington and Lake Champlain. Enjoy the spectacular views and relaxing atmosphere on your private deck. Although the apartment does not have air conditioning, it stays a cool 65 degrees on most days - you may even want to turn on the heat early on a summer morning! We require a minimum of a three-night stay.

Guest favourite

Tiny home in Duxbury

4.97 out of 5 average rating, 279 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 favourite

Apartment in Waterbury Center

4.9 out of 5 average rating, 208 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 favourite

Apartment in Hinesburg

4.93 out of 5 average rating, 287 reviews

Hilltop Haven

This peaceful spot rests between Burlington and Stowe in the largest section of the VAST trail with THE BEST mountain biking and hiking! This is a spacious loft efficiency apartment above a garage with a private balcony. Sugarbush, Mad River, Bolton Valley, Lake Champlain, all nearby. New hot tub! Cold plunge! Wifi and WiFi calling! New stove and fridge! You will need ALL-WHEEL DRIVE to get here in the WINTER and spring during MUD SEASON.

Guest favourite

Guest suite in Waterbury Center

4.93 out of 5 average rating, 453 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.

Top Guest favourite

Guest suite in Plainfield

4.95 out of 5 average rating, 414 reviews

House in beautiful rural Plainfield

Our house in rural Plainfield is a quiet place to enjoy Vermont's country roads, fields, mountains and night skies. Summer in Vermont is glorious, with blue skies, verdant fields, and full gardens. In fall, the maples turn red, orange, and gold. We welcome people of all races/nationalities. We strive to accommodate people with disabilities. We love to host families with babies and young children.

Top Guest favourite

Guest suite in Hinesburg

4.97 out of 5 average rating, 1,273 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 favourite

Home in Moretown

4.97 out of 5 average rating, 158 reviews

Lovely Waterbury Home (Crossroads of Recreation)

Nestled in the hills of Vermont, our home is a new 3 bedroom house with a large deck and finished basement. There's also a large yard outside for kids to run around. We're a short one-mile walk to downtown, where there is a quaint small-town feel. And once downtown, you'll find several restaurants and bars where you can sit outside and enjoy the fresh air.