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

Cabin in Richmond

4.94 out of 5 average rating, 156 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.

Mar 5 – 12

G$50,894 GYD per night

Guest favorite

Guest suite in East Montpelier

4.94 out of 5 average rating, 269 reviews

Cottage Farmhouse Apartment in Heart of Vermont!

A sweet, bright, spacious, private second floor cottage-apartment in our 1830's brick farmhouse, close to Montpelier the bustling state capital, completely redecorated for guests with a comfortable queen bed in the sleeping area, vintage farmhouse kitchen and lovely living/dining room. Refinished maple floors and travertine tiled bathroom with a rain shower. Nestled into the countryside with eastern mountain views & active farm fields -glorious morning sun and black-out shades for sleeping in.

Apr 21 – 28

G$24,890 GYD per night

Guest favorite

Cottage in Lincoln

4.87 out of 5 average rating, 857 reviews

The Barn at North Orchard, Near Middlebury

Our barn sits on an 80 acre estate with fab views of the Green Mts. near Middlebury/Burlington. Perfect for 2 adults and a child or grandparents/ 2 friendly couples. Close to skiing, hiking, lake & river swimming, great restaurants... local beer, wine, cheese!. Want yoga, pasta class, or massage? We will gladly hook you up. Or, you could stay in to read, work, and enjoy the serenity of the mountains. A very private garden patio for morning coffee/ afternoon beer or wine or awaits you.

Jan 1 – 8

G$25,910 GYD per night

Guest favorite

Apartment in Hinesburg

4.91 out of 5 average rating, 201 reviews

Backyard Bunker Retreat

Hot tub and cold plunge open! This peaceful spot rests beneath Camels Hump between Burlington and Stowe in the largest section of the VAST trail system with THE BEST mountain biking and hiking. Pet friendly! Fire pit! Trails! Less than 15 miles to Sugarbush and Mad River! This is a cozy basement apartment with a private deck. Gorgeous forest views and access. Close to Lake Champlain. You will need an ALL-WHEEL DRIVE vehicle to get here in the WINTER and spring during MUD SEASON.

Jul 24 – 31

G$29,510 GYD per night

Guest favorite

Yurt in New Haven

4.91 out of 5 average rating, 254 reviews

Song Bird Sangha Yurt

Songbird Sangha was thoughtfully created to provide a peaceful retreat from the world. It is nestled into a beautiful forest with privacy in mind. You will fall in love with the sky dome over your queen sized bed for the most comfortable star gazing ever! Your stay would not be complete without a complimentary campfire & marshmallow and if you would like more magic sign up for our Airbnb Experience The Healing Nature of Horses, a life enhancing encounter . Certified Wildlife Habitat.

Aug 10 – 17

G$26,586 GYD per night

Guest favorite

Apartment in Hinesburg

4.96 out of 5 average rating, 399 reviews

The Perfect Cozy Weekend Escape

From our reviews: "We were amazed with this place - could not have asked for a more perfect place to stay - immaculate - super comfortable bed! - wonderfully inviting - the photos do not do it justice at all - A picturesque Vermont country setting - The perfect retreat to get away from it all! - impeccably clean - simply fantastic - total privacy & idyllic setting - far exceeded our expectations! - perfect for a weekend escape - a space to feed your soul - absolutely amazing!”

Mar 15 – 22

G$28,012 GYD per night

Guest favorite

Guest suite in Waterbury Center

4.94 out of 5 average rating, 415 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.

Mar 19 – 26

G$11,342 GYD per night

Guest favorite

Apartment in Waterbury Center

4.89 out of 5 average rating, 174 reviews

Basecamp Waterbury - center of it all!

PLEASE READ FULL DESCRIPTION BEFORE BOOKING - and I prefer a message over instant book just to make sure you don't have any questions and I don't have any conflicts. You can't get more centrally located to everything Vermont has to offer. 5 minutes to downtown Waterbury, 10 minutes to Stowe, Half an hour to Burlington or Mad River. There is a shared hallway entry with the downstairs apartment but only the one exterior door in common.

Jun 8 – 15

G$25,400 GYD per night

Guest favorite

Cottage in Waitsfield

4.94 out of 5 average rating, 223 reviews

The Bent Hill Schoolhouse

The Tinmouth Vermont Schoolhouse c.1840, was moved and restored in 1981 to Bent Hill Settlement in Waitsfield Vermont. This charming, private one-room schoolhouse sits on 6 acres and has been newly updated in 2017. A fully equipped kitchen is at your disposal. Private bath off open living space. Bedroom upstairs in the garret. Outside patio table and gas BBQ grill.

Oct 22 – 29

G$23,208 GYD per night

Guest favorite

Home in Moretown

4.98 out of 5 average rating, 132 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.

Mar 21 – 28

G$37,108 GYD per night

Guest favorite

Guest suite in Hinesburg

4.96 out of 5 average rating, 1116 reviews

Boston Magazine Pick! Barn Loft

*** Chosen by Boston Magazine as one of five New England barns to rent! *** Beautiful barn loft close to Burlington, the Green Mountains and Lake Champlain. Air conditioning, 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.

Jun 22 – 29

G$34,385 GYD per night

Guest favorite

Loft in Waitsfield

4.93 out of 5 average rating, 147 reviews

Quiet, Cozy Loft w/ Mountain View’s! Remote Work!

Exceptional value. Charming, comfortable and cozy second story Loft. Open concept living with exposed beams and cathedral ceiling. A true rustic Vermont experience as you relax after a day of skiing, hiking, mountain biking, or simply enjoying the beauty of the Mad River Valley.

Nov 29 – Dec 6

G$31,833 GYD per night