
Vacation rentals in Middlebury
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Top-rated vacation rentals in Middlebury
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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.

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.

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.

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.

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.

The Little House
You will be close to everything the village of Middlebury has to offer when you stay at this centrally-located, light-filled home. A short walk to Middlebury's coffee shops, retail stores, and restaurants. Very close to Middlebury College and just minutes from hiking, biking, skiing, and many other outdoor activities in the mountains and on the shores of Lake Dunmore or Lake Champlain. Perfect for a quiet stay in town or as an adventure home base. Off-street parking for two cars.

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!

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.

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.

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.

East Wing 2nd Floor Apartment
Comfortable 2nd floor apartment in a contemporary farm house in rural Vermont. Stunning views and setting, surrounded by farmland and mountains. Close to beautiful Bristol Village, 20 minutes to Middlebury, 40 minutes to Burlington. ~30 minutes to Mad River Glen and Sugarbush ski areas.
Popular amenities for Middlebury vacation rentals
Other great vacation rentals in Middlebury

Little City Brick Apartment A

Updated Apartment Downtown

3 story contemporary log cabin

Cozy 1 bedroom guest suite in Lincoln VT

Renovated East Middlebury House

Welcome to the Hill

Scandinavian inspired studio

Walk Everywhere and Enjoy a Historic Vermont Home
Quick stats about vacation rentals in Middlebury
Total rentals
70 properties
Nightly prices starting at
$70 before taxes and fees
Total number of reviews
5.1K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Destinations to explore
- Okemo Mountain Resort
- Sugarbush Resort
- Smugglers' Notch Resort
- Spruce Peak
- Gore Mountain
- Bolton Valley Resort
- Whiteface Mountain Ski Resort
- Fort Ticonderoga
- Pico Mountain Ski Resort
- Cochran's Ski Area
- Autumn Mountain Winery
- Lucky Bugger Vineyard & Winery
- Montshire Museum of Science
- Fox Run Golf Club
- Northeast Slopes Ski Tow
- Country Club of Vermont
- Burlington Country Club
- Leahy Center for Lake Champlain
- Ethan Allen Homestead Museum
- Adirondack Extreme Adventure Course
- Vermont National Country Club
- Killington Adventure Center
- Lincoln Peak Vineyard
- Boyden Valley Winery & Spirits
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