Holiday rentals in Middlebury

4.99 out of 5 average rating, 149 reviews

Flat in New Haven

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.

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.

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.

Superhost

4.8 out of 5 average rating, 136 reviews

Middlebury Home with Sunset views!

This early-1900s Middlebury home has long been split as a duplex with an upper / lower apartment. We've made recent updates, decorated, and furnished the first floor unit for short term use and we know that you will have a positive experience here! This property offers a short walk to Main Street and is 1 mile to the Middlebury College campus, with easy access to the TAM (Trail Around Middlebury). You'll have everything you need to live in this space, just bring food and drink!

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

Flat 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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Popular amenities for Middlebury holiday rentals

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Other great holiday rentals in Middlebury

4.97 out of 5 average rating, 73 reviews

Flat in Bristol

2-Bedroom , 1 1/2 Bath Apartment with Mt Views.

GaryRating, 5 stars1 month ago

Amazing,Perfect,Comfortable,Everything you could ever need! Very clean. Perfectly located. Cheryl and Dan were fantastic hosts and went above and beyond to make our stay a very memorable one. We were treated like family, and we felt like we have known them for years. We would highly recommend them. And will “definitely “ rebook with them in the future. Their home is beautiful ( just as the pictures show and is described perfectly). We can’t thank them enough for making our extended Mother’s Day weekend with our children a special, memorable and enjoyable trip. You won’t be disappointed! Thank you so much…Gary, Christine, and Kim Bolk

4.91 out of 5 average rating, 22 reviews

Flat 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, 18 reviews

Updated Apartment Downtown

LucyRating, 5 stars1 week ago

Katherine’s apartment was so lovely, and perfect for our stay in Middlebury. It’s beautifully situated— we walked to and from town every night for dinner, and easily drove to explore the nearby lake and hiking trails—and the apartment itself is so clean and bright and comfortable! Every kitchen and toiletry item we could have needed is supplied, and the entrance to the apartment is very private. Katherine is very communicative and kind, and we felt thoroughly taken care of. We’ll be staying again next time we’re visiting Middlebury. Thank you for a wonderful stay!

Home in Middlebury

4.93 out of 5 average rating, 14 reviews

Buttolph Acres Hideway

JohnRating, 5 stars3 months ago

Close to downtown Middlebury, good location in a quiet neighborhood. House was clean and neat, and kitchen was nice. Had a good stay while working in town for the week.

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, 11 reviews

Flat 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, 5 reviews

Updated farmhouse minutes from Middlebury

R. TealRating, 5 stars1 week ago

Mary and Luis's place is absolutely fantastic! The details and quality of the photos are reflected ten-fold and more in the wonderful property. Every part of the house is spacious, and reflects an incredible attention to detail. From the Good Earth lemongrass lavender soap to the fascinating Vermont literature on the coffee table, everything is absolutely exquisite. The house was clearly remodeled recently with modern washer/dryer, lights, blinds, and more. I can't recommend this place enough for a Vermont getaway. Of the 10+ AirBnBs I've stayed at, this one was most beautifully and thoughtfully crafted. However, I'll note two small things that are beyond the control of the hosts: the house is located near a 45mph highway so there are (infrequent) car sounds at night if you leave the windows open, and the beautiful upstairs bedroom has slanted ceilings, so watch your head.