
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.

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

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..

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.

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!

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.

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
Other great vacation rentals in Middlebury

Updated Apartment Downtown

Peace of the Farm Guest House

3 story contemporary log cabin

Cozy 1 bedroom guest suite in Lincoln VT

Renovated East Middlebury House

Little City Brick Apartment B

Charming farmhouse at Sunrise Orchards

Farmhouse Sunset Suite
When is the best time to visit Middlebury?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$38,062 GYD | G$43,500 GYD | G$37,226 GYD | G$36,598 GYD | G$42,454 GYD | G$43,918 GYD | G$42,036 GYD | G$42,245 GYD | G$52,283 GYD | G$42,245 GYD | G$36,598 GYD | G$34,089 GYD |
| Avg. temp | -6°C | -5°C | 0°C | 8°C | 15°C | 20°C | 22°C | 21°C | 17°C | 10°C | 4°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!
Destinations to explore
- Okemo Mountain Resort
- Sugarbush Resort
- Gore Mountain
- Bolton Valley Resort
- Whiteface Mountain Ski Resort
- Fort Ticonderoga
- Cochran's Ski Area
- Pico Mountain Ski Resort
- Autumn Mountain Winery
- Lucky Bugger Vineyard & Winery
- Northeast Slopes Ski Tow
- Fox Run Golf Club
- Montshire Museum of Science
- Cozy Cottages & Otter Valley Winery
- Country Club of Vermont
- Burlington Country Club
- Ethan Allen Homestead Museum
- Leahy Center for Lake Champlain
- Adirondack Extreme Adventure Course
- Killington Adventure Center
- Vermont National Country Club
- Lincoln Peak Vineyard
- Shelburne Vineyard
- Snow Farm Vineyard & Winery