Middlebury Vacations from $355

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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.
Swanson Inn of Vermont
Stonybrook Motel & Lodge
The Village of Loon Mountain
Eagle Mountain House & Golf Club
Valcour Inn & Boathouse
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Middlebury Hotel Deals

Middlebury Inn

Middlebury Inn

3 out of 5
14 Court Square, Middlebury, VT
$172 nightly
The price is $189 total per night from Sep 23 to Sep 24
$189 total
Sep 23 - Sep 24
Total with taxes and fees
8.8/10 Excellent! (1,005 reviews)
"This is a beautiful old in, very well maintained. Friendly welcoming staff."

Reviewed on Aug 25, 2025

Middlebury Inn
Courtyard Middlebury

Courtyard Middlebury

3 out of 5
309 Court Street, US Rt 7 / Historic Ethan Allen Hwy, Middlebury, VT
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $157 total per night from Sep 7 to Sep 8
$157 total
Sep 7 - Sep 8
Total with taxes and fees
8.8/10 Excellent! (523 reviews)
"Daily or at least every other day housekeeping service would have been appreciated."

Reviewed on Aug 14, 2025

Courtyard Middlebury
Brandon Inn

Brandon Inn

3 out of 5
20 Park Street, Brandon, VT
$143 nightly
The price is $158 total per night from Aug 27 to Aug 28
$158 total
Aug 27 - Aug 28
Total with taxes and fees
8.6/10 Excellent! (507 reviews)
"A very old historic hotel. Has the oldest elevator in VT. Charming. Nice gardens. Guest can not use elevator and all rooms are upstairs. so if you have any mobility issues its a problem."

Reviewed on Aug 22, 2025

Brandon Inn
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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Frequently asked questions

How much does a Middlebury vacation package cost?
Offering excellent value package deals from $355 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.