Vacation rentals in Middlebury

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Top-rated vacation rentals in Middlebury

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Top guest favourite

Apartment in New Haven

4.99 out of 5 average rating, 153 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 favourite

Farm stay in Cornwall

4.95 out of 5 average rating, 129 reviews

Orchard Guesthouse - 1 mile to Middlebury

Orchard Guesthouse on our apple orchard is a delightfully unique place to stay. A former pickers cottage, we offer dorm style bedrooms and bathrooms with a rustic yet cozy interior. Includes full use of the house and adjacent yard. We are conveniently located 2 miles from Middlebury and 1 mile from Middlebury College campus. Come enjoy a full range of outdoor activities, adventure is on your doorstep! Perfect set up for groups - cycling, hiking, skiing (nordic/alpine) or college events.

Top guest favourite

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.

Top guest favourite

Apartment in Middlebury

5 out of 5 average rating, 190 reviews

Downtown 1 bedroom Apartment in Middlebury

Beautifully renovated upstairs apartment in the heart of downtown Middlebury, adjacent to Middlebury College, across from the Otter Creek Bakery and the new Middlebury town park. This charming space occupies 800 square feet above an optometry office in a Greek Revival home originally built circa 1856. It provides plenty of privacy and is within walking distance to all the restaurants and downtown shopping. A queen bed in the bedroom, and a pull out couch in the living room accommodates 4.

Top guest favourite

Farm stay in Salisbury

4.95 out of 5 average rating, 371 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 favourite

Cottage in New Haven

4.99 out of 5 average rating, 181 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.

Guest favourite

Apartment in Middlebury

4.97 out of 5 average rating, 104 reviews

Spacious Home Near Heart of Middlebury Fiber Wifi

Enjoy a cozy, stylish and private experience at this centrally located large 3 bedroom home. Free ultra fast Fiber Wifi. (4) 4k smart tv's including one large 65 inch curved for your enjoyment. Close to Middlebury College. Visit nearby hiking trails, Lake Dunmore, Branberry beach and much more. Near Middlebury College Snow Bowl and Robert Frost Trails for Beautiful nature views. Restaurants and shops within walking distance and a short drive or bike ride to downtown Middlebury.

Guest favourite

Apartment in Middlebury

4.98 out of 5 average rating, 139 reviews

Mountain View Retreat

This clean, quiet, ground-level apartment enjoys an out-of-town feel and expansive mountain views while being conveniently located to the town of Middlebury, Middlebury College, the Green Mountain National Forest, the Middlebury College Snow Bowl and the Rikert Nordic Center, and more. This 1 bedroom/1 bath apartment features an open living concept and a fully equipped kitchen and is just 1.5 miles from restaurants and grocery stores and 2 miles from the college.

Top guest favourite

Loft in New Haven

4.98 out of 5 average rating, 280 reviews

Sunrise over South Mountain

This is a spacious guesthouse/retreat where you can relax and unwind. There are great views and walking down the road is serene, with open fields bordered by woods and teaming with wildlife. In the winter you can Nordic ski or snowshoe right outside your door, through fields and woodland paths down by an active sugar-bush. We currently have chickens as well as my friendly dog Annie who loves to play. We also have a young kitty named LB who is a pip.

Top guest favourite

Guest suite in Cornwall

4.99 out of 5 average rating, 161 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 favourite

Home in Middlebury

4.89 out of 5 average rating, 177 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 favourite

Home in Middlebury

5 out of 5 average rating, 147 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.