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A river with a waterfall, a stone bridge, and buildings in the background.

Photo by David Alpert

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    Check prices for these dates, 14 – 15 December 2026

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    Our top choices for Middlebury holiday rentals

    1. Purple Door Cottage in the heart of Middlebury!

    A large grassy field with a historic building in the background.

    2. Charming one bedroom just minutes to Middlebury!

    A kitchen with wooden flooring, a refrigerator, and a double door with a frosted glass window.

    3. Tasteful two bedroom just minutes to Middlebury!

    A modern living room with a sofa, coffee table, and a dining area with chairs and a table.

    4. Glamping hut with WiFi in Ripton, biking, hiking, skiing

    A wooden deck with blue chairs and a barbecue grill.

    5. Gracious two bedroom just minutes to Middlebury!

    A grassy outdoor area with colorful Adirondack chairs arranged in a circle.

    6. Pristine Custom Cottage, Grand Piano, Massage Studio on Site

    A wooden deck with a bench and potted flowers, a small wooden structure with framed pictures, and a gravel path leading to a grassy area.

    7. Doc's Lake house 1st floor, 2 bedroom apartment

    Two Adirondack chairs facing a stream in a forested area.

    8. Private pet-friendly cabin in the woods w/ private campfire pit & screened porch

    A log cabin with a gravel driveway leading to it, surrounded by dense forest.

    9. Charming Barn Carriage House in Green Mountains of Vermont Near Middlebury

    An outdoor patio with a glass table and six chairs, surrounded by a wooden fence and a grassy area with trees in the background.

    10. Cozy and pristine timberframe cabin

    A log cabin with a green door, surrounded by snow-covered trees.

    11. Charming and meticulously cleaned cabin with panoramic view of the Green Mtns

    A log cabin with a porch, surrounded by trees.

    12. Welcoming, pet-friendly cabin in Green Mountain Nat'l Forest

    A log cabin with a green door, two windows, and a porch.

    13. Mountainside 63 first-floor ski-in/ski-out condo with garden-level patio

    A patio with a red Adirondack chair, a small table, and a black metal fence enclosing a swimming pool.

    14. Out to Lunch trail ski-in/ski-out condo with balcony and heated pool

    A rectangular swimming pool with a concrete deck, surrounded by trees and a fence.

    15. Beautiful home located in the Mad River Valley

    A forested area with a wooden deck and two white chairs.

    16. Beautiful home located in the Mad River Valley

    A forested area with a wooden deck and two white chairs.

    17. Beautiful home located in the Mad River Valley

    A picnic setup with a grill, chairs, and a wooden table in a forested area with autumn foliage.

    18. Light-filled Bridges condo overlooking the mountains, by the free shuttle

    An outdoor seating area with Adirondack chairs and a fire pit, surrounded by a grassy lawn and trees.

    19. The Bridges condo with balcony, two saunas and free coffee and tea

    A bathroom with a shower, toilet, sink, and mirror.

    20. The Bridges condo with forested views, three pools and two saunas

    A wooden Adirondack chair and a fire pit in a park with a mountain view.

    Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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    Top Middlebury Hotel Reviews

    Mad River Inn

    A row of Adirondack chairs in a lush green field with a backdrop of mist-covered hills and a purple sky.

    Shoreham Inn

    An outdoor patio with a table and chairs, surrounded by a grassy area and trees.

    Swift House Inn

    A large, multi-story house with a sign for 'Swift House Inn' indicating it is a lodging establishment.

    The Lilac Inn

    A glass bowl containing a dish with radishes, green onions, and a white sauce.

    White Horse Lodge

    A stone fireplace with a sign reading "Lodge" above it, a bear statue, and a wooden table with snacks and drinks.

    Lake Bomoseen Lodge

    A lakeside setting with a stone fire pit surrounded by logs, a grassy area, and a building with outdoor seating in the background.

    Mad River Barn

    A rustic bar area with a stone fireplace, wooden beams, and a bar counter with stools.

    The Warren Lodge

    Two wooden Adirondack chairs facing each other with a stone fire pit in between, set on a gravel path surrounded by trees and a stream.

    Lareau Farm Inn

    A rustic cabin with a metal roof, surrounded by a grassy area and trees.

    The Mountain Top Inn & Resort

    A spacious room with large windows, a stone wall, and a wooden ceiling.

    Find out more about Middlebury

    Everything you need to know about Middlebury holiday rentals

    Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middlebury holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

    There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middlebury holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

    Middlebury holiday rentals: An excellent choice for every season

    Whenever you want to travel, a warm welcome awaits you in Middlebury. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

    Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middlebury holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Middlebury holiday rentals we have selected for you start as low as £147 per night. Entering your travel dates in the search wizard you might find even better deals!

    How to find incredible deals on Middlebury rentals

    At Expedia, we put the best Middlebury holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

    To find some top Middlebury rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middlebury holiday.

    If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middlebury. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

    Frequently Asked Questions

    Are there holiday rentals in Middlebury?

    Yes, there are holiday rentals in Middlebury close to Vermont Folklife Center, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Middlebury has a good selection of restaurants. Make sure you have time to check out the architecture and university setting during your trip.

    How many holiday rentals are there in Middlebury?

    Expedia has 16 holiday rentals for your stay in Middlebury.

    What’s there to see and do in Middlebury?

    Cultural attractions include Town Hall Theater and Henry Sheldon Museum of Vermont History, whereas Green Mountain National Forest and Cornwall Swamp Wildlife Management Area are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include UVM Morgan Horse Farm and Vermont Folklife Center.

    What’s a holiday rental in Middlebury like?

    Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middlebury. Holiday rentals feature extras like WiFi and washers and dryers so you'll have everything you need. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy front desks while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for a small group gathering.