Holiday houses in Middlebury

Lovely Vermont Breadloaf Barn Stay Near Middlebury

Stay at our lovely renovated barn guesthouse in the Green Mountains of Vermont near Middlebury College. Perfect spot for a visit to campus, a quiet retreat, or home base for your outdoor adventure! 3 min. to Middlebury College’s Bread Loaf campus and Rikert Nordic Center, 9 min. to Middlebury SnowBowl. 40 min. to Sugarbush. 1 hr to Killington. Sleeps 1-6 people: entry level living area w/ laundry; mid-level with kitchen, bedroom, and bathroom ; upstairs loft suite with living area and desk.

Family · Value · Biking

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.

Family · Location · Condition

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!

Value · Location · Bathroom

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.

Family · Value · Walkability

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.

Location · Family · EV charging

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.

Location · Family · Heating

Modern Middlebury Retreat - Steps to Downtown

Welcome to your ideal Middlebury escape—where comfort, style, and location come together with ease. In the heart of town, this updated home places you just steps from local shops, dining, and everything Middlebury. Remodeled in 2020 with thoughtful attention to detail, the home features a bright, open-concept design that invites both relaxation and connection. Whether you’re here for a quiet getaway or visiting family and friends, there’s room for everyone to settle in and feel at home.

Value · Family · Getting around

Spacious Home • Near Downtown Middlebury.

Enjoy a cozy, stylish and private experience at this centrally located large 3 bedroom home. Free ultra fast Fiber Wifi. (4) 4k smart tv's including one large 65 inch curved for your enjoyment. Close to Middlebury College. Visit nearby hiking trails, Lake Dunmore, Branberry beach and much more. Near Middlebury College Snow Bowl and Robert Frost Trails for Beautiful nature views. Restaurants and shops within walking distance and a short drive or bike ride to downtown Middlebury.

Value · Family · Indoor spaces

Downtown Middlebury River House

Enjoy the perfect blend of in-town convenience and serene riverfront living in this newly remodeled home. Floor-to-ceiling windows showcase the Otter Creek river and flood the space with light. The home has a spacious open concept with elegant furnishings. Enjoy a peaceful rural Vermont escape with no neighbors in site - and yet easily walk into town or onto campus! **Listing is under new management so not many reviews; prior 42 reviews had an average 4.98 rating.

Location · Family · Bathroom

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.

Value · Family · Access

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.

Location · Family · Hot tub

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.

Family · Location · Checkout