Middlebury Vacations from $484

Book a Hotel + Flight or Car together to unlock savings

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.
Quality Inn South Bend Near Notre Dame

Quality Inn South Bend Near Notre Dame

2.5 out of 5
Price was $550, price is now $484 per person
$484
per person
Jun 23 - Jun 26
found 1 day ago
Roundtrip non-stop flight included
Las Vegas (LAS) to South Bend (SBN)
6.8/10 (441 reviews)
Friendly staff. Good for staying a couple of nights. Clean rooms

Reviewed on May 1, 2026

Morris Inn

Morris Inn

4 out of 5
Price was $888, price is now $723 per person
$723
per person
Jun 23 - Jun 26
found 1 day ago
Roundtrip non-stop flight included
Las Vegas (LAS) to South Bend (SBN)
10/10 Exceptional! (1,001 reviews)
Morris Inn was clean, the staff was overly friendly and helpful. Rohrs is a wonderful restaurant/bar on premise and they also have a delightful coffe shop.

Reviewed on May 12, 2026

The Inn at Saint Mary's

The Inn at Saint Mary's

3.5 out of 5
Price was $921, price is now $772 per person
$772
per person
Jun 23 - Jun 26
found 1 day ago
Roundtrip non-stop flight included
Las Vegas (LAS) to South Bend (SBN)
9.4/10 Exceptional! (1,158 reviews)
Great stay with great breakfasts

Reviewed on May 7, 2026

Ivy Court Inn & Suites

Ivy Court Inn & Suites

2.5 out of 5
Price was $868, price is now $743 per person
$743
per person
Jun 25 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Las Vegas (LAS) to South Bend (SBN)
9.2/10 Wonderful! (1,002 reviews)
Always a great experience. Will be back, usually 3x per year. N

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 $635, price is now $552 per person
$552
per person
Jun 23 - Jun 26
found 1 day ago
Roundtrip non-stop flight included
Las Vegas (LAS) to South Bend (SBN)
7.4/10 Good! (1,000 reviews)
Thanks for having us it was nice staff was welcoming. We will stay again

Reviewed on May 8, 2026

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
$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! (1,018 reviews)
The whole hotel experience was very nice. The breakfast was incredible!

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 $484 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.