
Holiday houses in Middlebury
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Top-rated holiday rentals in Middlebury
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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.

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.

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.

The Berghüttli: The Coziest Cabin in Vermont
The Berghüttli 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 Berghüttli provides a completely private mountain escape surrounded by National Forest. Take a VIDEO TOUR: search "The Berghüttli" on Youtube

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 holiday rentals
Other great holiday rentals in Middlebury

Centrally-located Victorian carriage house

Modern Apartment 1 in Middlebury

Cozy 1 bedroom guest suite in Lincoln VT

3 story contemporary log cabin

Renovated East Middlebury House

Upscale 4BR Cottage | Walk Downtown | Hot Tub

Little City Brick Apt B - Downtown Vergennes

Charming farmhouse at Sunrise Orchards
When is the best time to visit Middlebury?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $323 NZD | $370 NZD | $316 NZD | $311 NZD | $361 NZD | $373 NZD | $347 NZD | $361 NZD | $338 NZD | $359 NZD | $311 NZD | $290 NZD |
| 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 holiday rentals in Middlebury

Total holiday rentals
Explore 70 holiday rentals in Middlebury

Nightly prices starting at
Middlebury holiday rentals start at $124 NZD per night before taxes and fees

Verified guest reviews
Over 5,100 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
70 of Middlebury holiday 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
- Bolton Valley Resort
- Whiteface Mountain Ski Resort
- Fort Ticonderoga
- Pico Mountain Ski Resort
- Cochran's Ski Area
- Lucky Bugger Vineyard & Winery
- Autumn Mountain Winery
- Fox Run Golf Club
- Northeast Slopes Ski Tow
- Montshire Museum of Science
- Ethan Allen Homestead Museum
- Leahy Center for Lake Champlain
- Cozy Cottages & Otter Valley Winery
- Country Club of Vermont
- Burlington Country Club
- Adirondack Extreme Adventure Course
- Killington Adventure Center
- Vermont National Country Club
- Lincoln Peak Vineyard
- Shelburne Vineyard
- Whaleback Vineyard
- Snow Farm Vineyard & Winery




