Holiday houses in Middlebury

4.93 out of 5 average rating, 311 reviews

Yurt in Bristol

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..

4.92 out of 5 average rating, 169 reviews

Hut in Ripton

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.

4.93 out of 5 average rating, 231 reviews

Farm stay in Cornwall

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.

4.99 out of 5 average rating, 158 reviews

Home in Middlebury

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.

5 out of 5 average rating, 189 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.

4.95 out of 5 average rating, 358 reviews

Farm stay in Salisbury

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.

4.99 out of 5 average rating, 175 reviews

Cottage in New Haven

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.

4.92 out of 5 average rating, 286 reviews

Yurt in New Haven

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.

4.98 out of 5 average rating, 132 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.

4.99 out of 5 average rating, 157 reviews

Guest suite in Cornwall

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.

4.82 out of 5 average rating, 181 reviews

Cozy Apt. Near heart of Middlebury Fiber WIFI

Enjoy a cozy, stylish and private experience at this centrally-located apartment Free ultra fast Fiber Wifi, office desk + chair for work 2 smart Tv’s connected to wifi for your enjoyment 2.5 miles to Middlebury College. Visit nearby hiking trails, Lake Dunmore Branberry Beach see our guide for hiking and skiing and more! Restaurants and shops within walking distance and a short drive or bike ride to downtown Middlebury

4.86 out of 5 average rating, 155 reviews

Apartment in Bristol

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.

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4.91 out of 5 average rating, 22 reviews

Apartment in Vergennes

Little City Brick Apartment A

UdayRating, 5 stars3 weeks ago

Curtis was very responsive to a concern we raised about the heater in the bedroom not turning on. He brought his handyman with him and sorted out the issue in short order. His desire to make us feel comfortable was not lost on us and we would definitely consider staying here again if our travel plans bring us back to Vergennes.

5 out of 5 average rating, 33 reviews

Home in Middlebury

3 story contemporary log cabin

Douglas KennethRating, 5 stars3 weeks ago

We had a wonderful stay at Kurt’s place for Middlebury graduation. The house is very comfortable and had everything we needed for the weekend. Although it is about a 10 min drive from Middlebury, it is an easy drive and didn’t seem that far.

5 out of 5 average rating, 8 reviews

Modern Apartment 2 in Middlebury

MarkRating, 5 stars1 week ago

This apartment is new, spacious & clean! Great location. It was a perfect find. I wish I’d discovered it sooner (but it may not have existed)!

5 out of 5 average rating, 75 reviews

Guesthouse in Bristol

Studio Retreat

MaryRating, 5 stars3 weeks ago

Absolutely beautiful and peaceful studio! It was such a great location to access Bristol, Middlebury, and plenty of nearby hiking. We would happily stay here again!

5 out of 5 average rating, 11 reviews

Apartment in Bristol

Scandinavian inspired studio

MichaelRating, 5 stars1 week ago

David and Hannah have created a perfect Vermont getaway. The studio is stylish, spotless, and full of thoughtful touches. Bristol is a charming location with easy access to everything Vermont offers. The hosts are kind, responsive, and truly care about the guest experience. From the comfy bed to the well-appointed kitchen, everything was just right. We'll absolutely be back!

Home in Weybridge

5 out of 5 average rating, 4 reviews

Updated farmhouse minutes from Middlebury

DianeRating, 5 stars1 week ago

Hands down one of the best Air B and Bs I’ve been to, and I’ve been to a lot! Mary and Luis, our hosts, were so welcoming that we instantly felt like family. Their communication was great. We had an incredible stay at their charming, beautifully updated farmhouse in Vermont! The home is full of character, with thoughtfully curated antique decor that gives it a warm, welcoming feel. Every detail has been considered, from cozy linens and a fully stocked kitchen to extra touches that made our stay especially comfortable. The views from the property are stunning, with rolling hills and peaceful scenery in every direction. We loved being able to walk to downtown Middlebury—just a short stroll away—for great shops, restaurants, and a true New England village vibe. This place is the perfect blend of rustic charm and modern comfort. Whether you're relaxing indoors or enjoying the scenery outside, you’ll feel right at home. I highly recommend and would return in a heartbeat!

5 out of 5 average rating, 143 reviews

Bluebird Studio- Light filled and airy

AbbyRating, 5 stars3 weeks ago

Dutton’s place was perfect. We came for Middlebury’s commencement with our 6 year old and the location was excellent and quiet. Our son loved how cozy it was. The kitchen was really great to have on such a busy weekend. Dutton was super flexible and helpful too, letting us stay a few extra hours so our grad could finishing packing up her room. The bed was firm, just good to know. We all slept well. Absolutely recommend.