Holiday rentals in Middlebury

The Middlebury Cottage

A family, visiting professionals, vacationing couples, and recreation enthusiasts will all enjoy their stay at this Middlebury Cottage. You will be close to everything you want and need - the cottage is just a short bus ride from the Middlebury Amtrak Station, within walking distance of Middlebury College, downtown Middlebury, the Middlebury Food Coop, and the 19-mile Trail Around Middlebury. Just a short drive brings you to Rikert Nordic Center, Middlebury Snow Bowl, the Long Trail, and more!

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.

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.

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

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.

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.

Middlebury Bungalow

Comfy, quiet and all yours! Whether you’re here to visit Middlebury College, hit the slopes, hike, run, bike, or dine downtown — this centrally located home lets you do it all! Featuring an open floor plan with two bedrooms, two bathrooms and an office w/a pull-out bed, this home comfortably accommodates up to six overnight guests. This bungalow is located in a peaceful neighborhood 1 mile from Middlebury College. While you’re here, don’t miss the Middlebury Falls lit up at night!

The Berghüttli: Glowing Swiss Hut in the Forest

The Berghüttli ("little mountain hut") is a Swiss-inspired hut and farm stay surrounded by National Forest in Goshen, VT (pop. 168). A completely private escape—no other structures in sight, just woods and quiet. Inside, a wall of windows brings the forest right up to you, while glowing maple plywood fills the space with warm light. High-speed fiber internet runs a reliable 300 Mbps. Stay connected or switch off completely. Search "The Berghüttli" on YouTube for a video tour.

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.

Historic Farmhouse in Middlebury

We offer a historic, four bedroom farmhouse in a peaceful, rural setting surrounded by wetlands, forrest, and farms. This is a family and pet friendly property with a private entrance, full kitchen, living and dining areas, full and half bathrooms, access to our fenced backyard, and dedicated laundry facilities. By making arrangements ahead of your stay, you can use our 3 season barn; send us a message letting us know how and when you would like to use it.

Chipman Hill Apartment.

This elegant apartment in our home on Chipman Hill in Middlebury is a short walk to town and Middlebury College and steps away from the Chipman Hill forest, with its miles of hiking and biking trails and many scenic vistas. A private entrance leads to a screened porch, living room, kitchen, and bathroom on the second floor. Skylights in the large third-floor bedroom offer breathtaking views of the Champlain Valley and the Adirondack Mountains.

Walk Everywhere and Enjoy a Historic Vermont Home

This historic 1860's home has been uniquely renovated to feature it's history combined with modern comfort. The kitchen is the focal place in the home which opens into the dining room. Watch the sunset from the back deck or while soaking in the hot tub! Original wood floors, tin ceilings, doors/door handles, etc. will take you back in time. This oasis in town provides back yard gardens and walking distance to downtown shops/restaurants.