Middlebury Vacations

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 ₩234,741 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

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 ₩150,660 per night from Aug 3 to Aug 4
₩150,660
₩168,739 total
Aug 3 - Aug 4
includes taxes & fees
8.2/10 Very Good! (1,009 reviews)
"The two guys who were on duty at the front desk when we checked in were wonderful. They were welcoming and helpful. Both had a sense of humor which made the experience even more pleasant. Later, when we left for the evening, they both stepped outside with us to guide us with directions to our destination. ..."

Reviewed on Jul 20, 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 ₩147,871 per night from Jul 27 to Jul 28
₩147,871
₩165,627 total
Jul 27 - Jul 28
includes taxes & fees
9.6/10 Exceptional! (1,010 reviews)
"Super clean room and bathroom. We felt like we were staying at a friend’s home."

Reviewed on Jul 22, 2025

Essenhaus Inn & Conference Center
Farmstead Inn & Conference Center

Farmstead Inn & Conference Center

2.5 out of 5
370 S Van Buren St, Shipshewana, IN
Fully refundableReserve now, pay when you stay
The price is ₩194,400 per night from Jul 27 to Jul 28
₩194,400
₩217,733 total
Jul 27 - Jul 28
includes taxes & fees
9.6/10 Exceptional! (1,008 reviews)
"First time staying in Shipshewana. Quiet, simple, and quaint little town. Inn was comfortable, quiet, and convenient…we enjoyed the stay."

Reviewed on Jul 20, 2025

Farmstead Inn & Conference Center
See all 536 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 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.