Middlebury Holidays

Photo by David Alpert

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to €185 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    Rest easy

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

Top hotels in Middlebury

Middlebury Inn

Middlebury Inn

3 out of 5
14 Court Square, Middlebury, VT
The price is €140 per night from 16 Sept to 17 Sept
€140
16 Sept - 17 Sept
includes taxes & fees
8.8/10 Excellent! (1,005 reviews)
"The oldest continuously operating hotel in the States but it doesn’t seem that way. The lobby is spacious, the staff friendly and helpful. The rooms are good sized, TV, WiFi, A/C, soft but comfy beds. We stayed in the original part of the hotel, but they also have newer buildings in back. There is ..."

Reviewed on 17 Aug 2025

Middlebury Inn
Courtyard Middlebury

Courtyard Middlebury

3 out of 5
309 Court Street, US Rt 7 / Historic Ethan Allen Hwy, Middlebury, VT
The price is €135 per night from 7 Sept to 8 Sept
€135
7 Sept - 8 Sept
includes taxes & fees
8.8/10 Excellent! (522 reviews)
"Daily or at least every other day housekeeping service would have been appreciated."

Reviewed on 14 Aug 2025

Courtyard Middlebury
Brandon Inn

Brandon Inn

3 out of 5
20 Park Street, Brandon, VT
The price is €142 per night from 24 Aug to 25 Aug
€142
24 Aug - 25 Aug
includes taxes & fees
8.6/10 Excellent! (504 reviews)
"The only problem is the elevator that is not accessible to everyone"

Reviewed on 16 Aug 2025

Brandon Inn
See all 917 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.

Popular places to visit

Halpin Covered Bridge

Learn about the local history of Middlebury when you take a trip to Halpin Covered Bridge. Stroll along the riverfront or visit the cathedral while you're in the area.

Halpin Covered Bridge

Frequently asked questions

How much does a Middlebury holiday package cost?
Offering excellent value package deals on Expedia, you'll be surprised at how little a holiday 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 holiday package, consider travelling 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 holiday, a handful of days will be enough to tour the best spots. Be sure to check out Town Hall Theatre — 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 holiday package to Middlebury?
It's easy to see why a Middlebury holiday is on the to-do list of many travellers. 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 holiday package as soon as possible.
Is it cheaper to book a Middlebury holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to booking flights and hotels separately. Better still, you can customise 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 holiday 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 accommodation: Once you've settled on your trip dates and duration, book the ideal Middlebury holiday package for you.

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