Family-friendly vacation rentals in Middlebury

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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 ground-level exterior of a blue wooden building shows a sloped roof with dormer windows. A welcoming front door is flanked by two seating chairs on a stone pathway, surrounded by lush green grass and flower beds.

Apartment in New Haven

4.99 out of 5 average rating, 165 reviews

Charming one bedroom just minutes to Middlebury!

Just minutes away from Middlebury College, this well designed 1 bedroom is the perfect place for a stress-free getaway! Great location for parents to stay when visiting their Midd kids. The renovated apartment is well appointed with central heating/AC, super fast WiFi, laundry machines, full kitchen, full en suite bathroom with bath and shower, brand new queen bed and mattress, a great room with dining, cozy seating, and a 65" smart TV. This clean and tidy unit is the definition of easy living.

Top 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, 342 reviews

Bristol Cozy Yurt near Hiking/Foliage|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 spacious living area features a queen size bed with a blue quilt, adjacent to a cozy fireplace. Green armchairs and a small round table provide additional seating. Tall curtains frame windows, and a bookshelf adds a touch of color to the wall.

Apartment in Middlebury

4.99 out of 5 average rating, 159 reviews

Bluebird Studio- Light filled and airy

This studio apartment attached to the main house has a style all its own. Contemporary design with high ceilings, clerestory windows and a skylight. Spaces include a large Living Room/Bedroom, Kitchen/Dining area, bathroom with a step-in shower and an adjoining Dressing Room with vanity and sink. There is also an outdoor covered space to enjoy. Furniture includes a Queen size bed, 3 comfy chairs, small round table and 4 chairs. Location is a bit more than one mile from downtown Middlebury.

Guest favorite

A compact hut is nestled among greenery, featuring a wooden deck with two blue chairs. Nearby, a picnic table and a red grill are visible on the grass, with trees providing a natural backdrop against a cloudy sky.

Hut in Ripton

4.93 out of 5 average rating, 174 reviews

Breadloaf Hut. Glamping, hiking, biking, foliage

Hiker, writers’, gravel/mountain biker's paradise! Our quiet glamping retreat provides easy access to miles of wilderness. The hut has a cozy bed, kitchenette, and camping basics making for an easy and cozy getaway. Follow a trail to the Catamount Trail or drive a few minutes to the Long Trail. Enjoy miles of gravel biking from the door or go to Moosalamoo or Rochester for prime mountain biking trails. In the evening, sit on the deck under a blanket of stars and warm your toes by the fire.

Guest favorite

The exterior of a charming cottage apartment is surrounded by vibrant orange flowers and lush greenery. Large windows reflect natural light, and a covered porch provides a shaded area. Mature trees add to the welcoming atmosphere of the property.

Apartment in Middlebury

4.91 out of 5 average rating, 113 reviews

The Cottage Apartment in downtown Middlebury.

This charming, 1st floor two-bdr. cottage apartment is steps from Main Street, downtown Middlebury, & walking distance to shops, restaurants, and the College. An historic college town, Middlebury is replete with great restaurants, shops and cultural events to enjoy, all within walking distance. The comforts of this home include private parking, gardens, separate entrance, full kitchen and bath, and sleeps four. It is only a half hour from The Middlebury College Snow Bowl, and Lake Champlain.

Top guest favorite

The cozy cottage is softly illuminated at night, with warm light emanating from the windows. A sliding door is positioned at the entrance, complemented by two outdoor chairs on the lush lawn. The moonlight adds a serene ambiance to the rural scene.

Farm stay in Salisbury

4.95 out of 5 average rating, 392 reviews

Quaint 1-bedroom cottage on Blue Ledge Farm

This cozy cottage is on Blue Ledge Farm- a working goat dairy. It is a one-bedroom with a double fold-out futon in living room to potentially fit 4 guests. It is within 15 minutes of both Brandon and Middlebury, 1 hour south of Burlington. Pets are allowed, on leash. It can possibly include a farm and cheese tasting for an extra $20 per person (contact host in advance). It is the perfect place if you're an animal or cheese lover looking for a rustic and relaxing stay on a beautiful farm.

Top guest favorite

Cottage in New Haven

4.99 out of 5 average rating, 186 reviews

Hilltop Cottage With a View

Our newly built cozy and relaxing guest cottage is located in New Haven . It has stunning views and gorgeous sunsets!! Located just seven miles from Middlebury ,Vergennes and Bristol . All of which have great shops and restaurants! Close to many local attractions including ,Woodchuck Cider house, Lincoln Peak Vineyard, Ski areas, Hiking , rivers, lakes, restaurants and much more! Our goal was to provide guests with a home away from home! We feel our cottage offers that and much more.

Top guest favorite

Two Adirondack chairs are positioned on a well-manicured lawn, overlooking a serene landscape of grassy fields and scattered trees. A backdrop of rolling hills can be seen under a partly cloudy sky, evoking a sense of tranquility in a rural setting.

Guest suite in Cornwall

4.99 out of 5 average rating, 168 reviews

Home Suite Home in Cornwall, Minutes from Midd!

Looking for a home away from home on your travels in the Champlain Valley? Whether you're searching for a place to lay your head while visiting your Middlebury College student, a home base while exploring the gorgeous Green Mountain State, or a secluded, peaceful retreat in which to write the next chapter of your book, we've got just the spot! Our home, with the private guest suite and deck, is situated perfectly for your Vermont holiday.

Guest favorite

A vibrant autumn landscape is captured, featuring a variety of trees adorned with bright orange, red, and yellow leaves. A winding river is visible in the foreground, surrounded by the lush greenery of the season. Overcast skies provide a soft light over the scene.

Apartment in Bristol

4.85 out of 5 average rating, 170 reviews

Overlook at the Office

Fall in love with Bristol. This sweet one-bedroom efficiency right in the Gateway to the Green Mountains has everything you need, whether you are looking for a short weekend getaway or longer seasonal stay. Opening up this listing with all new small-kitchen appliances, queen bed, and new bathroom. Central to the town park and stores, and only miles away from ski areas, hiking trails, and water activities.

Top guest favorite

A charming two-story white building features a black metal roof and multiple windows with shutters. A covered porch extends across the front, decorated with vibrant flower baskets. Surrounding greenery contributes to the rural setting, with the presence of a neighboring structure visible in the background.

Apartment in Hancock

4.96 out of 5 average rating, 167 reviews

Suite in the Green Mountains

We have a first-floor,two-room suite with its own entrance in our home, located on an official Vermont Scenic Highway, in the middle of the Green Mountains. The suite has a large sitting room with a kitchenette; a bedroom with queen bed and A/C; and bathroom with tub/shower. NOTE: We have a second, larger unit in our home called "Two-Bedroom Apartment in the Green Mountains".

Top guest favorite

An updated kitchen space is presented with a central wooden island and three tall chairs. Exposed brick and wooden beams complement modern cabinetry. Natural light floods the area through a nearby window, revealing a view of the outside.

Home in Middlebury

5 out of 5 average rating, 155 reviews

In the heart of Middlebury, a modern farmhouse

This beautifully RENOVATED 3BR, 1.5 bath home merges its FARMHOUSE HERITAGE with MODERN décor and comforts. It is perfectly located on SOUTH STREET, perhaps the most sought-after address in Middlebury because it is nestled right between the heart of campus and this quintessential New England town. Both are just under a 5 min walk away.

Top guest favorite

A vibrant sunset casts rich hues of orange and pink across the sky, reflecting on a tranquil pond. Lush greenery and distant hills outline the serene landscape, creating a peaceful rural setting that invites relaxation.

Apartment in Bristol

4.95 out of 5 average rating, 99 reviews

East Wing 2nd Floor Apartment

Comfortable 2nd floor apartment in a contemporary farm house in rural Vermont. Stunning views and setting, surrounded by farmland and mountains. Close to beautiful Bristol Village, 20 minutes to Middlebury, 40 minutes to Burlington. ~30 minutes to Mad River Glen and Sugarbush ski areas.