Middlebury Vacations from $1,003
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Your Middlebury Vacation
Our vacation packages to Middlebury let you customize your own adventure. Tailor your journey to your interests and needs and make the most of your time in this fabulous city. You'll want to do some exploring during your trip to Middlebury. Make time for major attractions such as Middlebury College, National Museum of the Morgan Horse and UVM Morgan Horse Farm. A couple of clicks is all it takes to build the perfect Middlebury vacation on Expedia.
The Latest Middlebury vacation packages
Price found within the past 48 hours. Click for updated prices.
Club Wyndham Smugglers’ Notch Vermont
$1,662
per person
Oct 10 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Burlington (BTV)
8.6/10 Excellent! (227 reviews)
The rooms were clean and spacious. The kitchen was well stocked. The shuttle to Lot 6 was nice. The map was useless for finding things. Too many things were closed on Monday.
Reviewed on Aug 25, 2026
Stay near popular Middlebury attractions
Pulp Mill Covered Bridge
9.6/10 (20 reviews)
One of America's oldest double-barreled covered bridges, this 19th-century wooden marvel spans Otter Creek with its distinctive kingpost truss design. Photographers capture its charm against Vermont's seasonal backdrops.
Middlebury College
9.6/10 (285 reviews)
Founded in 1800, Middlebury College offers a stunning campus where historic architecture meets the Green Mountains of Vermont. Explore the Old Chapel in this prestigious liberal arts setting.
UVM Morgan Horse Farm
9.4/10 (13 reviews)
This historic breeding facility preserves America's first native horse breed with guided tours through scenic barns. Meet Morgan horses up close during the May-October visiting season.
Vermont Folklife Center
9.6/10 (4 reviews)
Enjoy an outing to Vermont Folklife Center during your stay in Middlebury. While you're here, you can savor the top-notch restaurants.
Henry Sheldon Museum of Vermont History
8.0/10 (1 review)
America's oldest community-based museum houses Vermont treasures in the historic 1829 Judd-Harris House. Explore period rooms with authentic 19th-century furniture and rotating exhibits in the Walter Cerf Gallery.
Kevin P. Mahaney '84 Center for the Arts
10.0/10 (10 reviews)
This cultural cornerstone houses Middlebury College's art museum, theaters, and a stunning recital hall. Visitors can immerse themselves in diverse exhibitions and performances by both local and international artists.
Cornwall Swamp Wildlife Management Area
Explore the great outdoors at Cornwall Swamp Wildlife Management Area, a lovely green space in Cornwall.
Halpin Covered Bridge
9.4/10 (19 reviews)
Vermont's highest covered bridge stands 41 feet above the Muddy Branch, showcasing 19th-century craftsmanship. Photographers capture its wooden architecture against seasonal backdrops of vibrant foliage or lush greenery.
Middlebury Hotel Deals
Middlebury Inn
14 Court Square Middlebury VT
Fully refundableReserve now, pay when you stay
$147 nightly
$161 total
Sep 15 - Sep 16
Total with taxes and fees
9/10 Wonderful! (1,006 reviews)
"The Inn was centrally located to the shops in downtown Middlebury."
Reviewed on Sep 2, 2026
Courtyard Middlebury
309 Court Street Middlebury VT
Fully refundableReserve now, pay when you stay
$179 nightly
$197 total
Sep 15 - Sep 16
Total with taxes and fees
9/10 Wonderful! (598 reviews)
"It was a very convenient location. There is a restaurant/bar, which was nice. The woman at the desk was incredibly friendly and helpful. We were very pleased with our stay and would stay there again."
Reviewed on Aug 29, 2026
Swift House Inn
57 North Pleasant Street Middlebury VT
$249 nightly
$274 total
Sep 14 - Sep 15
Total with taxes and fees
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.
Find the Best Middlebury Vacation Packages
Middlebury Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 6,600 |
Max Temp Winter | 30ºF |
Max Temp Summer | 75ºF |
Top Sights | Branbury State Park, Otter Creek Brewing and Lincoln Peak Vineyard |
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Frequently asked questions
How much does a Middlebury vacation package cost?
Offering excellent value package deals from $1,003 on Expedia, you'll be surprised at how little a vacation to Middlebury costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Middlebury?
If you're hoping to snag a cheap Middlebury vacation package, consider traveling in September, October and December. You'll generally find better rates on airfares and hotels during these months — perfect for a budget-friendly break.
How many days is enough for Middlebury?
Generally, a few days is ideal for a Middlebury vacation. With a carefully crafted itinerary, you can go to all the main sights such as Town Hall Theater, as well as explore some hidden gems along the way.
Is it worth booking a vacation package to Middlebury?
Middlebury is a good vacation destination with attractions like UVM Morgan Horse Farm among the many things to keep you entertained. Whether you're heading away with the family or getting away with friends, a Middlebury vacation promises fun for everyone.
How to find the best Middlebury package deals?
Use Expedia's handy filters to find some great Middlebury package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or search for Middlebury package deals in the off-season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a Middlebury vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and hotels separately. Better still, you can customize your Middlebury getaway to match your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Middlebury?
If you have your Middlebury travel dates locked in, book as early as you can to grab some awesome deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are perfect for impromptu escapes.
Does Expedia offer Book Now, Pay Later Middlebury vacation packages?
Jet off on your ideal getaway to Middlebury with help from our Book Now, Pay Later vacations. There's no need to scrimp and save or wait until payday — we've teamed up with online lender Affirm to offer you flexibility and choice. Our vacation packages with payment plans let you split the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, it's a breeze to budget for your trip and snap up cheap deals before they sell out.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.