Vacation rentals in Middlebury

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Middlebury

Guests agree: these stays are highly rated for location, cleanliness, and more.

%{current} / %{total}1 / 1
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, 166 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 cozy bedroom features a spacious bed adorned with plush white linens and two yellow accent pillows. Nightstands flank the bed, each with a lamp, while a circular mirror reflects the warm ambiance. The blue-green walls enhance the room's serene atmosphere.
Guesthouse in Salisbury
4.94 out of 5 average rating, 125 reviews

Welcoming Retreat Near Middlebury & Lake Dunmore

Come swim, hike, or ski while staying at our welcoming and comfortable 2nd floor studio apartment with plush linens, comfortable King bed, a well equipped kitchenette plus space to relax, work & play. + Garage parking. -Single Family home also now available as1 or 2 BRs 7 min from Middlebury with all its amenities 5 min from Lake Dunmore 13 min from Brandon 16 min from Rikert Outdoor Center for cross country 18 min from Snowbowl for down hill skiing 32 miles - approx 50 mins from Killington

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
4.92 out of 5 average rating, 346 reviews

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..

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, 163 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
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
4.92 out of 5 average rating, 118 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
A bright living area features tall windows allowing natural light to fill the space. A comfortable white sofa, accent chairs, and a wooden coffee table are positioned on warm wooden flooring. A bookshelf with numerous books adds character, while a desk provides a workspace.
Apartment in Middlebury
5 out of 5 average rating, 211 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.

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, 397 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, 188 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 favorite
An open dining area features a wooden table surrounded by benches, with a bar counter and stools extending towards the kitchen. Exposed brick walls and hardwood floors provide a warm atmosphere. Natural light enters through a door leading to an outdoor porch, adorned with greenery.
Apartment in Middlebury
4.82 out of 5 average rating, 150 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!

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, 172 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
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, 158 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 charming cottage is surrounded by a grassy area, featuring a red umbrella over a small outdoor table and chairs. Two white lounge chairs are positioned nearby, complemented by greenery and tall trees in the background.
Home in East Middlebury
5 out of 5 average rating, 474 reviews

Nice one bedroom cottage

Located at the foot of the Green Mountains, a short walk to the Waybury Pub, nearby hiking, fishing and skiing. 4 miles to heart of Middlebury. Full kitchen, living room, bedroom(queen bed) and bathroom with stand up shower. ethernet connection/cable tv/washer-dryer/ac/ns

Popular amenities for Middlebury vacation rentals

When is the best time to visit Middlebury?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$38,062 GYDG$43,500 GYDG$37,226 GYDG$36,598 GYDG$42,454 GYDG$43,918 GYDG$42,036 GYDG$42,245 GYDG$52,283 GYDG$42,245 GYDG$36,598 GYDG$34,089 GYD
Avg. temp-6°C-5°C0°C8°C15°C20°C22°C21°C17°C10°C4°C-2°C

Quick stats about vacation rentals in Middlebury

  • Total vacation rentals

    Explore 70 vacation rentals in Middlebury

  • Nightly prices starting at

    Middlebury vacation rentals start at G$14,639 GYD per night before taxes and fees

  • Verified guest reviews

    Over 5,100 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    70 of Middlebury vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Middlebury rentals

  • 4.9 Average rating

    Middlebury stays are highly rated by guests—averaging 4.9 out of 5!

  1. Airbnb
  2. United States
  3. Vermont
  4. Addison County
  5. Middlebury