Middlebury Vacations

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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 ￥21,972 per night from Jul 27 to Jul 28
￥21,972
￥24,169 total
Jul 27 - Jul 28
includes taxes & fees
9/10 Wonderful! (1,010 reviews)
"My comment is specific. I lost a pair of sunglasses and inquired at the reception desk whether a pair had been found. The person at reception said something like "no, not since I've been at the desk". But what about during the prior shift? She couldn't be bothered to get up out of her chair to look. ..."

Reviewed on Jul 10, 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 ￥23,136 per night from Jul 26 to Jul 27
￥23,136
￥25,450 total
Jul 26 - Jul 27
includes taxes & fees
9/10 Wonderful! (580 reviews)
"This was a great hotel. I would definitely stay there again. Highly recommended."

Reviewed on Jul 9, 2026

Courtyard Middlebury
Swift House Inn

Swift House Inn

3 out of 5
57 North Pleasant Street Middlebury VT
The price is ￥36,385 per night from Jul 13 to Jul 14
￥36,385
￥40,023 total
Jul 13 - Jul 14
includes taxes & fees
9.6/10 Exceptional! (344 reviews)
"We stayed in one of the rooms in the Carriage House (as opposed to the Main House). It's by the road but wasn't too loud. The grounds are impeccably kept, with beautiful flowers and veggies growing everywhere. We enjoyed the buffet breakfast (shout-out to Linus for being the most friendly and welcoming ..."

Reviewed on Jul 7, 2026

Swift House Inn
See all 985 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

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.
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.

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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.