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Places to stay near Middlebury College

Book unique holiday rentals, homes and more on Airbnb

Top-rated holiday rentals near Middlebury College

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

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Top guest favourite
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.
Flat in Middlebury
4.99 out of 5 average rating, 178 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.

Top guest favourite
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.
Flat in Middlebury
4.92 out of 5 average rating, 139 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 favourite
A queen-sized bed is positioned against a wooden wall with slanted ceilings. Large triangular windows provide views of the surrounding forest and mountains, allowing natural light to fill the space.
Home in Keene
4.97 out of 5 average rating, 222 reviews

Ascent House | Keene

A unique retreat meticulously crafted for resting and recharging after exploring in our beautiful Adirondack Wilderness. Flooded with natural light, every room offers calming frames of nature. Watch the sun peak through the forest and rise over the mountains through expansive windows. Ascend the levels of the house, each revealing more landscape. Experience a designer woodfired traditional Finnish sauna & totally recharge while embracing our harsh Adirondack weather. We hope you love it here.

Top guest favourite
A unique treehouse is seen perched among tall trees, with a blend of rustic wood siding and large windows that reflect the surrounding greenery. The structure stands elevated from the ground, supported by slender pillars, blending harmoniously with the natural forest environment.
Treehouse in Hancock
4.98 out of 5 average rating, 168 reviews

Weasley's Enchanted Treehouse @ Vermont ReTREEt

Welcome to our enchanting treehouse! We crafted this unique and magic inspired dwelling for any admirer of a beloved wizarding world, or anyone who appreciates isolation in a fun space. As you cross the elevated walkways, you'll feel like you're entering a wizards treehome in the forest. The 1,100 sqft treehouse is nestled in and among trees, providing a magical and secluded escape from life. Have a question or hesitations? reach out check out our other listings for glamping style treehouses

Top guest favourite
The exterior of the cottage displays a modern design with light gray siding and a vibrant purple door. A small porch offers space to relax, while surrounding trees enhance the peaceful environment. A pathway is visible, leading to the entrance of the home.
Home in Middlebury
4.97 out of 5 average rating, 197 reviews

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.

Top guest favourite
Cottage in New Haven
4.99 out of 5 average rating, 193 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
A modern house with wooden exterior is shown from an elevated perspective, surrounded by autumn foliage. A hot tub is positioned on a spacious deck, which includes a seating area with four chairs and a small table. Scenic mountain views and vibrant trees enhance the natural setting.
Tiny home in Warren
4.99 out of 5 average rating, 303 reviews

Luxury Glass Tiny House - Mountain View + Hot Tub

Immerse yourself in nature at Vermont's most unique Airbnb, located in the heart of the Green Mountains. This upscale mirrored glass house was built in Estonia and combines Scandinavian design with jaw-dropping Vermont views for an unforgettable experience. You'll return home feeling rejuvenated after relaxing in a hot tub overlooking Sugarbush Mountain or waking up with a panorama of Blueberry Lake at your feet. *One of Airbnb’s Most Wish-listed Stays of 2023*

Top guest favourite
The exterior of the guesthouse is shown, featuring a white wooden facade with multiple windows. A prominent cupola tops the structure, reflecting sunlight under a clear blue sky. Lush green trees and shrubs surround the building, enhancing the serene ambiance of the area.
Guest house in Vergennes
4.98 out of 5 average rating, 132 reviews

Private Guesthouse in the heart of Vergennes

Completed in 2013, the Guesthouse perfectly complements the 1871 Victorian home to which it is attached. Located on Main Street in historic Vergennes, Vermont, our home is one of several fine examples of the architecture of the 19th Century that grace our City. Our thriving downtown is a short walk away, boasting exceptional dining and shopping opportunities. Vergennes is a 20-minute drive away from Middlebury College, and 45 minutes from Burlington.

Top guest favourite
The single-story home features a modern wooden exterior with large windows that allow natural light to enter. A spacious deck is equipped with outdoor seating and leads to a grassy area surrounded by trees. The inviting structure presents a blend of warmth and contemporary design.
Home in Starksboro
4.99 out of 5 average rating, 157 reviews

Forest Hideaway

Our single story 2 bedroom 1 bath home is located within 30 minutes of Mad River Glen and Sugarbush ski areas and the quaint towns of Bristol, Richmond and Waitsfield. Drive another 15 minutes to Burlington or the Bolton Valley Ski Area. Hiking, biking and cross country skiing trails are nearby, or just sit on the porch and enjoy the sounds of the nearby river. Snow tires and front wheel or 4 wheel drive vehicles necessary during the winter months.

Top guest favourite
An open-concept kitchen and dining area is furnished with modern appliances and sleek cabinetry. A central island provides additional counter space, while a dining table with four chairs is positioned nearby. Natural light filters through windows, enhancing the space's bright and airy feel.
Home in Weybridge
5 out of 5 average rating, 119 reviews

Close to college-cheerful, quiet, 2 bedroom home

This recently renovated home is conveniently located 1.5 miles from Middlebury College campus and all that Middlebury has to offer! The back deck and spacious yard are perfect for relaxing outdoors. The open floor plan is cozy for one and accommodates families well. The master bedroom is furnished with a queen bed and the second bedroom has two twin beds. Pack 'n Play and highchairs are available for young children upon request.

Top guest favourite
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, 168 reviews

In the heart of Middlebury, a modern farmhouse

This beautifully RENOVATED 3BR, 1.5 bath home merges its FARMHOUSE HERITAGE with MODERN dĂŠcor 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.

Guest favourite
A bright living area features large windows that frame views of the surrounding forest. Natural light enhances the wood-paneled walls. A comfortable sofa and chair are positioned around a central coffee table. A small, modern wood stove provides warmth, creating a cozy atmosphere.
Cabin in Goshen
4.97 out of 5 average rating, 138 reviews

The BerghĂźttli: The Coziest Cabin in Vermont

The BerghĂźttli is a Swiss-inspired mountain hut and farm stay located in Goshen, VT (population 168). Inspired by the tradition of mountain huts in the alps, the BerghĂźttli provides a completely private mountain escape surrounded by National Forest. Take a VIDEO TOUR: search "The BerghĂźttli" on Youtube

Popular amenities for holiday rentals near Middlebury College

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