Middlebury Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Ann Sair

  • Plan, book, travel with confidence

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    Better together

    Save up to NT$5,067 when you book a flight and hotel together*
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    Find the right fit

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

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

Find the Best Middlebury Vacation Packages

Middlebury Hotel Deals

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 NT$3,050 per night from Aug 24 to Aug 25
NT$3,050
NT$3,416 total
Aug 24 - Aug 25
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
"Room is clean and operational"

Reviewed on 2025/8/17

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! (1,006 reviews)
Great place to Stay
"We have stayed at the Eesenhaus a number of times and always enjoy it."

Reviewed on 2025/8/16

Get rates
Essenhaus Inn & Conference Center
Travelodge by Wyndham Elkhart

Travelodge by Wyndham Elkhart

2 out of 5
115 Northpointe Blvd, Elkhart, IN
Fully refundableReserve now, pay when you stay
The price is NT$1,860 per night from Sep 1 to Sep 2
NT$1,860
NT$2,083 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
Five stars… Wood stay here again!
"A great place to stay when passing through the area. Rooms were nice and clean and well kept, staff was friendly, the small continental breakfast was a nice option plus there is also several restaurants right next-door if you need to go bigger. I would definitely stay here again."

Reviewed on 2025/8/17

Travelodge by Wyndham Elkhart
See all 524 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.

Discover the most popular places to visit in Middlebury

Deutsch Kase Haus

Enjoy an outing to Deutsch Kase Haus during your stay in Middlebury. While in this relaxing area, find time to visit its shops.

Deutsch Kase Haus

Frequently asked questions

How much does a Middlebury vacation package cost?
You can pick up a vacation package to this destination on Expedia. However, how much your vacation 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 vacation 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 travelers.
How many days is enough for Middlebury?
The ideal length for your Middlebury vacation 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 vacation package well in advance.
Is it cheaper to book a Middlebury vacation as a package?
You can enjoy significant savings on your next Middlebury getaway by booking a tailored vacation 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 vacation 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, favorite 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 accommodations 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 accommodations: Once you've settled on your dates and duration, lock in the perfect Middlebury vacation package for you.

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