Middlebury Vacations from $674

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

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.

The Latest Middlebury vacation packages

Price found within the past 48 hours. Click for updated prices.
Ivy Court Inn & Suites

Ivy Court Inn & Suites

2.5 out of 5
Price was $850, price is now $674 per person
$674
per person
Jun 18 - Jun 22
found 15 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to South Bend (SBN)
9.2/10 Wonderful! (1,002 reviews)
Very nice property clean room great location, helpful staff great continental breakfast perfect for my needs

Reviewed on May 13, 2026

Doubletree Hotel South Bend

Doubletree Hotel South Bend

4 out of 5
Downtown South Bend
Price was $1,094, price is now $892 per person
$892
per person
Jun 18 - Jun 22
found 15 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to South Bend (SBN)
7.6/10 Good! (1,002 reviews)
When we went the elevators were broke down. It was very hard to climb 7 flights of stairs with a fused foot. They did give us a discount but it caused me a lot of extra pain. The hotel has been under construction for years. We expected it to be done and ready.

Reviewed on May 11, 2026

La Quinta Inn & Suites by Wyndham South Bend

La Quinta Inn & Suites by Wyndham South Bend

3 out of 5
Price was $811, price is now $679 per person
$679
per person
Jun 18 - Jun 22
found 15 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to South Bend (SBN)
7.4/10 Good! (1,001 reviews)
Standard no frills - good price

Reviewed on May 12, 2026

The Inn at Saint Mary's

The Inn at Saint Mary's

3.5 out of 5
Price was $987, price is now $827 per person
$827
per person
Jun 18 - Jun 22
found 15 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to South Bend (SBN)
9.4/10 Exceptional! (1,158 reviews)
Breakfast menu was fresh but not much variety

Reviewed on May 12, 2026

Hot Tub Outdoor Living Game Room Coffee Bar

Hot Tub Outdoor Living Game Room Coffee Bar

2 out of 5
Price was $1,447, price is now $1,246 per person
$1,246
per person
Jun 18 - Jun 22
found 15 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to South Bend (SBN)
No reviews
Don't see what you're looking for?
See all available trips from Columbus to Middlebury
View all trips

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

Middlebury Hotel Deals

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
$119 nightly
The price is $133 total per night from May 17 to May 18
$133 total
May 17 - May 18
Total with taxes and fees
9.6/10 Exceptional! (1,000 reviews)
We enjoyed the atrium very much . The staff were definitely friendly and helpful and extremely professional.The hotel itself was nice and quiet and spotless. The breakfast was difficult due to my allergies so we went out to eat each of the five days.

Reviewed on May 12, 2026

Essenhaus Inn & Conference Center
Hampton Inn & Suites Middlebury

Hampton Inn & Suites Middlebury

2.5 out of 5
105 Crystal Heights Blvd Middlebury IN
$126 nightly
The price is $141 total per night from May 24 to May 25
$141 total
May 24 - May 25
Total with taxes and fees
8.4/10 Very Good! (1,006 reviews)
The staff was friendly and greeted as you entered, rooms were clean and plenty of food for breakfast

Reviewed on May 10, 2026

Hampton Inn & Suites Middlebury
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

Middlebury IN
$175 nightly
The price is $187 total per night from May 17 to May 18
$187 total
May 17 - May 18
Total with taxes and fees
10/10 Exceptional! (50 reviews)
We had a thoroughly enjoyable stay. We chatted with the owner, Mike. It was very quiet and peaceful and just exactly what my soul needed. Mike was quick to respond to any and all questions, we fell in love with the house and the whole area. I will definitely stay there next time we're in the ...

Reviewed on May 4, 2026

Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
See all 574 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.

Find the Best Middlebury Vacation Packages

Middlebury Essential Information

Language
English
Currency
U.S dollars
Population
3,600
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Puppet Parlor Theatre, Wine Cellar Supply Winery and Elkhart County Fairgrounds

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Middlebury vacation package cost?
You can pick up a vacation package to this destination from $674 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 book a cheap Middlebury vacation package, consider traveling in January, October and November. You'll generally find better rates on airfares and hotels during these months — perfect 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 do. Generally, a few days to a week will give you plenty of time to visit all the major sights and discover some hidden treasures 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.
Does Expedia offer Book Now, Pay Later Middlebury vacation packages?
If you're like us, you love discovering new places but don't love the big price tag that can sometimes come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the overall cost of your Middlebury break across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you see them.

Explore a world of travel with Expedia

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