Holiday houses in Middlebury

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Top-rated holiday rentals in Middlebury

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A round yurt is surrounded by lush green trees, with a tan conical roof and large windows that invite natural light. The pathway leading to the entrance is bordered by various plants and shrubs, enhancing the connection to the natural setting.
Yurt in Bristol
4.93 out of 5 average rating, 347 reviews

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..

Top Guest favourite
A spacious living area features a queen size bed with a blue quilt, adjacent to a cozy fireplace. Green armchairs and a small round table provide additional seating. Tall curtains frame windows, and a bookshelf adds a touch of color to the wall.
Apartment in Middlebury
4.99 out of 5 average rating, 164 reviews

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.

Guest favourite
The exterior of a charming cottage apartment is surrounded by vibrant orange flowers and lush greenery. Large windows reflect natural light, and a covered porch provides a shaded area. Mature trees add to the welcoming atmosphere of the property.
Apartment in Middlebury
4.92 out of 5 average rating, 119 reviews

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.

Top Guest favourite
A bright living area features tall windows allowing natural light to fill the space. A comfortable white sofa, accent chairs, and a wooden coffee table are positioned on warm wooden flooring. A bookshelf with numerous books adds character, while a desk provides a workspace.
Apartment in Middlebury
5 out of 5 average rating, 211 reviews

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.

Top Guest favourite
The exterior of the cottage displays a modern design with light gray siding and a vibrant purple door. A small porch offers space to relax, while surrounding trees enhance the peaceful environment. A pathway is visible, leading to the entrance of the home.
Home in Middlebury
4.97 out of 5 average rating, 179 reviews

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.

Top Guest favourite
The cozy cottage is softly illuminated at night, with warm light emanating from the windows. A sliding door is positioned at the entrance, complemented by two outdoor chairs on the lush lawn. The moonlight adds a serene ambiance to the rural scene.
Farm stay in Salisbury
4.95 out of 5 average rating, 397 reviews

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.

Top Guest favourite
Cottage in New Haven
4.99 out of 5 average rating, 188 reviews

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.

Guest favourite
An open dining area features a wooden table surrounded by benches, with a bar counter and stools extending towards the kitchen. Exposed brick walls and hardwood floors provide a warm atmosphere. Natural light enters through a door leading to an outdoor porch, adorned with greenery.
Apartment in Middlebury
4.82 out of 5 average rating, 150 reviews

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!

Guest favourite
A vibrant autumn landscape is captured, featuring a variety of trees adorned with bright orange, red, and yellow leaves. A winding river is visible in the foreground, surrounded by the lush greenery of the season. Overcast skies provide a soft light over the scene.
Apartment in Bristol
4.85 out of 5 average rating, 172 reviews

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.

Top Guest favourite
An updated kitchen space is presented with a central wooden island and three tall chairs. Exposed brick and wooden beams complement modern cabinetry. Natural light floods the area through a nearby window, revealing a view of the outside.
Home in Middlebury
5 out of 5 average rating, 158 reviews

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.

Top Guest favourite
A bright living area features large windows that frame views of the surrounding forest. Natural light enhances the wood-paneled walls. A comfortable sofa and chair are positioned around a central coffee table. A small, modern wood stove provides warmth, creating a cozy atmosphere.
Cabin in Goshen
4.98 out of 5 average rating, 127 reviews

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

Top Guest favourite
A charming cottage is surrounded by a grassy area, featuring a red umbrella over a small outdoor table and chairs. Two white lounge chairs are positioned nearby, complemented by greenery and tall trees in the background.
Home in East Middlebury
5 out of 5 average rating, 474 reviews

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

When is the best time to visit Middlebury?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
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
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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!

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