Middlebury Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Ann Sair

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to £335 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
    Packages with flights are ATOL protected

Your Middlebury Holiday

When a city adventure is calling, answer it with a Middlebury holiday package. With all your travel needs under control before you go, all you have to do here is focus on having a ball. During your trip to Middlebury, give yourself enough time for sightseeing. A fantastic place to begin is Deutsch Kase Haus. Browse Expedia's extensive range of travel options and book your ideal holiday to Middlebury today.

Middlebury Essential Information

Language
English
Currency
U.S dollars
Population
3,600
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Puppet Parlor Theatre, Wine Cellar Supply Winery and Elkhart County Fairgrounds

Our pick of the best Middlebury Hotel Deals

Hampton Inn & Suites Middlebury
Hampton Inn & Suites Middlebury
2.5 out of 5
105 Crystal Heights Blvd, Middlebury, IN
Stay at this hotel in Middlebury. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their reviews. ...
8.4/10 Very Good! (1,003 reviews)
"Pool was great, hot tub great, beautiful place. Our room was huge and unique design."

Reviewed on 19 Jun 2025

Hampton Inn & Suites Middlebury
Essenhaus Inn & Conference Center
Essenhaus Inn & Conference Center
3.5 out of 5
240 Hwy 20, Middlebury, IN
Stay at this 3.5-star business-friendly hotel in Middlebury. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful ...
9.6/10 Exceptional! (1,000 reviews)
"Very comfortable, wonderful free breakfast, pleasant atrium to relax, shops, restaurants & bakery to visit & beautiful grounds to stroller."

Reviewed on 24 Jun 2025

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, IN
Stay at this cottage in Middlebury. Enjoy free Wi-Fi, a garden and patios. Popular attractions Blue Gate Theater and East Lake are located nearby.
9.8/10 Exceptional! (15 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 537 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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does a Middlebury travel package cost?
Live it up in Middlebury from as low as . We offer a great selection of rental cars, hotels and flights to suit your travel style. You can score even better deals when you add some tours or activities to your travel package.
If I'm not able to travel, can I cancel my Middlebury travel package?
Don't stress if you're rethinking your Middlebury travel package --- you can cancel or amend your booking. And if you've booked it within 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur charges from your airline, hotel or car rental company. We know life can sometimes throw a spanner in the works, so look up our Customer Service Portal if that happens. When you're ready to make changes, we're here to help.
How do I get a cheap travel package to Middlebury?
Crafting your own Middlebury travel package with Expedia is one of the easiest ways to save. We have more than 550 air carriers and 1,000,000 hotel options around the world. With such an amazing range to choose from, you'll have no issues creating your perfect getaway.
Does Expedia offer Book Now, Pay Later Middlebury holidays?
We certainly do. Expedia has partnered with online lender Klarna to help you easily pay for your holiday in instalments. Simply click on the payment plan that suits best during checkout and take away the stress of budgeting for your trip. Make sure you bundle your flights, car hire and hotel with Expedia to get the biggest bang for your travel buck. Check out our flexible payment options below:
  • Pay monthly holidays: Make your holiday dreams a reality sooner with Klarna's easy monthly instalment plans. If paying just a little each month sounds right for you, choose this option at checkout.
  • Pay in instalments holidays: If you'd prefer to pay for your escape in multiple transactions, holidays paid in instalments might be right for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than the full total upfront) makes it easier to click that "book now" button, go for a low deposit holiday payment plan with Klarna.

Where should I stay in Middlebury?
Middlebury is home to numerous popular places to see, such as Deutsch Kase Haus. Stay somewhere close by and make sightseeing a breeze.
What are the top hotels in Middlebury?
Secure a room at Holiday Inn Express & Suites Elkhart, an IHG Hotel. It's one of this neighbourhood's most in-demand properties. Another top option in Middlebury is Microtel Inn & Suites by Wyndham Elkhart.
How far in advance should I book my Middlebury holiday?
Savvy travellers book early. Airlines generally release flight tickets up to a year in advance, and this is a perfect opportunity to score some of the cheapest prices. Boss just told you to take some holiday time next month? That's alright! Expedia are never short on fantastic bargains to send you on the getaway of your dreams, at an affordable price.
What does an Expedia Middlebury travel package include?
Choose from any combination of rental cars, flights and hotels. Once you've made your booking, you can add some activities and tours. Want to pick your airfare class? That's easily done too. The choice is yours when it comes to crafting your perfect Middlebury escape.
What should I know before booking a Middlebury travel package?
Get ready to save with an Expedia travel package. Bundle your flights, rental cars and hotels and be rewarded with great discounts. Hotels aren't your only choice, though. We have island villas, city apartments and just about everything in between!
Can I choose my airline with a Middlebury Expedia travel package?
Yes, and with more than 550 airlines to pick from all over the world, you've got lots of choice. Search the available options and see which airline best suits your budget and needs.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.