Family-friendly vacation rentals in Middlebury

Private constructed yurt on organic farm

Take it easy at this unique and tranquil getaway. The entire constructed yurt is yours to enjoy privately. Nestled on an organic farm, it sits a bit above Bristol offering sweeping views of the valley and the beautiful Adirondack mountains. There are many farm animals on the property and farm tours are available upon request. PLEASE NOTE: The queen bed is only accessible by a ladder. The property is located up a steep driveway. During the winter months all wheel drive vehicles are required.

Bristol Cozy Yurt near Hiking/Skiing|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..

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.

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.

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.

Purple Door Cottage in the heart of Middlebury!

Purple Door Cottage is located in the heart of Middlebury on a peaceful side street. Completely renovated, AC & heat everywhere, lots of comfy beds, great deck with grill and fire ring, fast WiFi, king bedroom for the parents, fun guest room with 1 queen, 1 full & 1 twin, full bath & 1/2 bath. Walk to restaurants, shops, grocery stores, and even the College! Incredibly well designed home can comfortably accommodate a couple or a crowd! Brand new 55" Smart TV, new beds, linens, sofas, etc.

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.

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.

Historic Farmhouse in Middlebury

We offer a historic, four bedroom farmhouse in a peaceful, rural setting surrounded by wetlands, forrest, and farms. This is a family and pet friendly property with a private entrance, full kitchen, living and dining areas, full and half bathrooms, access to our fenced backyard, and dedicated laundry facilities. By making arrangements ahead of your stay, you can use our 3 season barn; send us a message letting us know how and when you would like to use it.

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.

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.

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.