Middlebury Holidays

Photo by Ann Sair

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Top hotels in Middlebury

Hampton Inn & Suites Middlebury
Hampton Inn & Suites Middlebury
2.5 out of 5
105 Crystal Heights Blvd, Middlebury, IN
Fully refundableReserve now, pay when you stay
The price is €109 per night from 6 Jul to 7 Jul
€109
6 Jul - 7 Jul
includes taxes & fees
8.2/10 Very Good! (1,008 reviews)
"Would have given it a 5-star rating, except our room was directly above the lobby and we could here the sliding doors opening & closing through the night. No view out the window either because the roof over drive-up area blocked the entire window! There shouldn't even be a guest room in that position...they ..."

Reviewed on 27 Jun 2025

Hampton Inn & Suites Middlebury
Essenhaus Inn & Conference Center
Essenhaus Inn & Conference Center
3.5 out of 5
240 Hwy 20, Middlebury, IN
Fully refundableReserve now, pay when you stay
9.6/10 Exceptional! (1,001 reviews)
"Very comfortable, wonderful free breakfast, pleasant atrium to relax, shops, restaurants & bakery to visit & beautiful grounds to stroller."

Reviewed on 24 Jun 2025

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Essenhaus Inn & Conference Center
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
2 out of 5
Middlebury
The price is €127 per night from 10 Jul to 11 Jul
€127
10 Jul - 11 Jul
includes taxes & fees
9.8/10 Exceptional! (16 reviews)
"This little house exceeded our expectations! It was clean and comfortable, well-stocked, and cozy. It is conveniently located between Middlebury and Shipshewana, with restaurants and shopping less than 10 minutes away. We will definitely stay here when we visit the area again!"

Reviewed on 11 Jun 2025

Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
See all 535 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.

Frequently asked questions

How much does a Middlebury holiday package cost?
You can pick up a holiday package to this destination on Expedia. However, how much your holiday to Middlebury costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Middlebury?
If you'd like to score a cheap Middlebury holiday package, consider planning a trip in January, February and November. You'll generally find better rates on airfares and hotels during these quieter months --- ideal for budget-conscious travellers.
How many days is enough for Middlebury?
The ideal length for your Middlebury holiday depends on what you'd like to see. Generally, a handful of days to a week will give you time to check out all the main sights and discover some hidden gems along the way.
How to find the best Middlebury package deals?
Use Expedia's handy filters to help you find some unbeatable 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 trip for midweek, or search for Middlebury package deals in the off-peak season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your holiday package well in advance.
Is it cheaper to book a Middlebury holiday as a package?
You can enjoy significant savings on your next Middlebury getaway by booking a tailored holiday package. Check the "Package" heading, then select your travel dates and destination to view the best hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a holiday package to Middlebury?
Enjoy fantastic discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu Middlebury getaway.
How to plan a trip to Middlebury?

  1. Choose the ideal time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to visit Middlebury.
  2. Calculate your budget: Make sure you have enough money to pay for everything from transportation and food to activities and airfares. Your accommodation will likely be the largest expense during your trip to Middlebury.
  3. Decide how long to go for: Now that you know more about Middlebury, you can work out the ideal length of your break. Create a draft plan and allocate enough time to cover everything you want to see.
  4. Bundle your airfare and accommodation: Once you've settled on your dates and duration, lock in the perfect 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.