Family-friendly vacation rentals in Middlebury

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Middlebury

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

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Top guest favorite

A serene sleeping area features a spacious bed with crisp white linens and a decorative throw. Soft lighting from wall sconces illuminates the wooden accent wall. Nearby, windows provide natural light, while the adjoining bathroom is visible through an open door.

Guest suite in Bristol

5 out of 5 average rating, 107 reviews

Modern Vermont Village Farmhouse - Guest House

Our home is located in the middle of the beautiful village of Bristol; our private guesthouse is only a few minutes walk to town with great restaurants, a few bars, shopping, and specialty stores. The village of Bristol is in the heart of the Green Mountains close to Middlebury and Burlington, major ski areas, Lake Champlain, minutes to Vermont's best mountains, rivers, swimming holes, fishing, hiking, and biking. We have lived here over 25 years and we will be happy to guide you any way we can.

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

The living area showcases a warm wooden ceiling and a mix of seating options, including a red futon and a bright yellow armchair. A patterned area rug adds texture to the wooden floor, complemented by two lamps providing soft lighting. A dining table is visible, inviting shared meals.

Apartment in Bristol

4.92 out of 5 average rating, 148 reviews

Peaceful Getaway in Bristol Village.

Simple beauty, generous space and peace, in a second floor one bedroom guest apartment with bathtub, shower and galley kitchen without stove. Double futon in living area for additional guests. A very sweet private getaway for a couple, or group of friends or small family. Bristol is a true New England find with an active arts community, good restaurants and shops, as well as several yoga and tai chi instructional groups. Settle your energy here and enjoy life. Skiing and hiking nearby.

Guest favorite

A simple yet inviting guesthouse features wooden siding and a metal roof. The front is lined with large windows, enhancing natural light. A wooden deck provides seating, with a grassy lawn extending towards the surrounding trees and fields.

Farm stay in Cornwall

4.93 out of 5 average rating, 234 reviews

Cozy country guest house

Our guesthouse is nestled in the Lemon Faire River Valley. This 1 bedroom with kitchen, bathroom, and extra sleeping loft gives you a quiet experience of the Vermont countryside. The outside entry deck overlooks over a 1000 acres of open field and farmland. Middlebury is only 3 miles away and offers museums, restaurants, and shopping. This is an active farm: horses, dogs, geese, a duck, and chickens. Please read the house manual as it has lots more information about the house and property.

Top guest favorite

A bright living area features tall windows allowing natural light to fill the space. A comfortable white sofa, accent chairs, and a wooden coffee table are positioned on warm wooden flooring. A bookshelf with numerous books adds character, while a desk provides a workspace.

Apartment in Middlebury

5 out of 5 average rating, 204 reviews

The Barn at Middlebury

The Barn at Middlebury is within a 10 min. walk of the village center and 15 min to Middlebury College. The renovated barn is attached to the owners' residence. The separate guest quarters have a private entrance and include 3 newly renovated bedrooms, with two baths. The 1st floor bedroom has a Livingroom, kitchenette (Nespresso, microwave, Ref/Freezer, dishwasher, sink). Washer/Dryer. The 2 other 2nd Fl bedrooms share a large private bath. A terrace and screened porch is available.

Guest favorite

The exterior of a blue house is framed by lush gardens and trees in various autumn colors. A stone wall in the foreground adds a rustic element, while several large windows allow natural light to fill the interior spaces.

Cottage in Lincoln

4.87 out of 5 average rating, 918 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.

Top guest favorite

An open interior perspective of a yurt reveals a cozy seating area with plush pillows and a patterned blanket. Above, a skylight allows natural light to illuminate the space. A staircase leads to a lofted area, while a dining set is positioned in the background.

Yurt in New Haven

4.92 out of 5 average rating, 289 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.

Top guest favorite

An open living area features hardwood flooring, a comfortable sofa, and decorative elements like pumpkins. The adjacent kitchen is visible with modern cabinetry and a dining space. Natural light flows in through the windows, enhancing the welcoming ambiance of the gathering space.

Home in Middlebury

4.96 out of 5 average rating, 106 reviews

Middlebury Gem open concept, 5 minutes from town

This home is in the middle of Middlebury and within walking distance to everything. It is perfect for just two or a large group or family. This open concept was completely remodeled in 2020, it has an amazing fully equipped commercial kitchen, just installed A/C on all floors and 3 large bedrooms, 2.5 baths and a great gathering and living space and great front porch and back deck. The living area, kitchen and dining are downstairs and all three bedrooms upstairs.

Guest favorite

The exterior of a charming Victorian house features a white façade and a welcoming front porch adorned with flower boxes. Lush greenery and colorful wildflowers frame the area, while a blue recycling bin is placed nearby, highlighting the home's inviting curb appeal.

Home in Middlebury

4.89 out of 5 average rating, 175 reviews

Entire House in Middlebury - Walk Everywhere

An entire, charming, turn-of-the-century Victorian in the heart of downtown Middlebury, Vermont all to yourself! A short distance from Main Street, you are within walking distance to downtown boutiques, restaurants, art galleries, and Middlebury college. A fully outfitted, newly remodeled kitchen gives you the freedom to prepare your own meals. Two king size beds and all the beds are new, ensuring a comfortable sleep!

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.