Middlebury Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ₩1,660,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Middlebury Vacation Packages

Middlebury Hotel Deals

Middlebury Inn

Middlebury Inn

3 out of 5
14 Court Square Middlebury VT
Fully refundableReserve now, pay when you stay
The price is ₩182,649 per night from Jul 5 to Jul 6
₩182,649
₩200,914 total
Jul 5 - Jul 6
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
"Right in the middle of town! Charming and comfortable. A wonderful bakery, Otter Creek Bakery , is just a few blocks away!"

Reviewed on Jul 1, 2026

Middlebury Inn
Courtyard Middlebury

Courtyard Middlebury

3 out of 5
309 Court Street Middlebury VT
Fully refundableReserve now, pay when you stay
The price is ₩229,080 per night from Jul 7 to Jul 8
₩229,080
₩251,988 total
Jul 7 - Jul 8
includes taxes & fees
8.8/10 Excellent! (576 reviews)
"Clean, comfortable beds. Beautiful setting with great view outside our window."

Reviewed on Jul 3, 2026

Courtyard Middlebury
Swift House Inn

Swift House Inn

3 out of 5
57 North Pleasant Street Middlebury VT
The price is ₩358,380 per night from Jul 20 to Jul 21
₩358,380
₩394,218 total
Jul 20 - Jul 21
includes taxes & fees
9.6/10 Exceptional! (343 reviews)
"Great room!"

Reviewed on Jun 28, 2026

Swift House Inn
See all 982 properties in Middlebury
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.

Stay near popular Middlebury attractions

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.
See properties

Frequently asked questions

How much does a Middlebury vacation package cost?
Offering excellent value package deals 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 book a cheap Middlebury vacation package, consider traveling in January, March and November. You'll typically find better rates on airfares and hotels during these months — ideal for a budget-friendly getaway.
How many days is enough for Middlebury?
When planning your Middlebury vacation, a handful of days will be enough to tour the best spots. Be sure to check out Town Hall Theater — it's one of the top attractions in this destination. If you want more adventure, think about basing yourself here and going on some tours from Middlebury.
Is it worth booking a vacation package to Middlebury?
It's easy to see why a Middlebury vacation is on the to-do list of many travelers. Popular attractions like Henry Sheldon Museum of Vermont History are just the start of what you can explore here.
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.
How to plan a trip to Middlebury?

  1. Choose when to go: Check your diary and get your bags packed. Your preferred season and the activities on offer will also help you decide when to escape to Middlebury.
  2. Figure out your budget: Ensure you have enough money to cover everything from transportation and meals to activities and airfares. Your hotel will likely be the largest expense during your trip to Middlebury.
  3. Work out your trip length: Consider how long you want to spend exploring Middlebury. Plan your days so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Bundle your airfare and accommodations: Once you've settled on your trip dates and duration, book the ideal Middlebury vacation package for you.

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.