Middlebury Vacation Packages

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Your Middlebury Vacation

When a city adventure is calling, answer it with a Middlebury vacation 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 vacation to Middlebury today.

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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 CA $125 per night from Feb. 10 to Feb. 11
CA $125
CA $140 total
includes taxes & fees
Feb 10 - Feb 11
8.4/10 Very Good! (1,005 reviews)
"The hotel was fine, but I felt it was a little overpriced for the quality."

Reviewed on Feb. 1, 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
The price is CA $159 per night from Feb. 9 to Feb. 10
CA $159
CA $178 total
includes taxes & fees
Feb 9 - Feb 10
9.6/10 Exceptional! (1,000 reviews)
"We love the Essenhaus and stay whenever we can."

Reviewed on Jan. 26, 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
The price is CA $160 per night from Feb. 3 to Feb. 4
CA $160
CA $202 total
includes taxes & fees
Feb 3 - Feb 4
9.6/10 Exceptional! (6 reviews)
"The property was very clean. Cottage was in excellent shape. The property owner was VERY nice and quick on replying. It was out in the country but close to Middlebury and Shipshewana. Definitely will stay again when we come back up."

Reviewed on Nov. 9, 2024

Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
See all 517 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 Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

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.