Middlebury Vacations from $471

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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.

The Latest Middlebury vacation packages

Price found within the past 48 hours. Click for updated prices.
Sleep Inn Elkhart North

Sleep Inn Elkhart North

2.5 out of 5
Price was $566, price is now $471 per person
$471
per person
Jun 26 - Jul 2
found 14 hours ago
Roundtrip non-stop flight included
San Antonio (SAT) to South Bend (SBN)
6.8/10 (859 reviews)
The rooms are nice smell good when you walk in. The beds are cozy. My kids loved the pool and the hot tub.They stay open till 1am. The breakfast is one of the perks we love.

Reviewed on May 17, 2026

The Inn at Saint Mary's

The Inn at Saint Mary's

3.5 out of 5
Save 100% on your flight
Price was $1,746, price is now $1,348 per person
$1,348
per person
Jun 26 - Jul 2
found 14 hours ago
Roundtrip non-stop flight included
San Antonio (SAT) to South Bend (SBN)
9.4/10 Exceptional! (1,168 reviews)
Stayed here many times and always pleasant. Lots of construction right now has temporarily cramped conditions and removed some amenities. Can’t wait for completion- hopefully everything is even better than before.

Reviewed on May 19, 2026

La Quinta Inn & Suites by Wyndham South Bend

La Quinta Inn & Suites by Wyndham South Bend

3 out of 5
Price was $803, price is now $628 per person
$628
per person
Jun 26 - Jul 2
found 14 hours ago
Roundtrip non-stop flight included
San Antonio (SAT) to South Bend (SBN)
7.4/10 Good! (1,005 reviews)
Standard no frills - good price

Reviewed on May 12, 2026

Ivy Court Inn & Suites

Ivy Court Inn & Suites

2.5 out of 5
Price was $952, price is now $745 per person
$745
per person
Jun 26 - Jul 2
found 14 hours ago
Roundtrip non-stop flight included
San Antonio (SAT) to South Bend (SBN)
9.2/10 Wonderful! (1,005 reviews)
The room is a little outdated. There is mold in the shower, but the rest of the room was extremely clean.

Reviewed on May 15, 2026

Hot Tub Outdoor Living Game Room Coffee Bar

Hot Tub Outdoor Living Game Room Coffee Bar

2 out of 5
Price was $1,603, price is now $1,321 per person
$1,321
per person
Jun 26 - Jul 2
found 14 hours ago
Roundtrip non-stop flight included
San Antonio (SAT) to South Bend (SBN)
No reviews
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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 31 to Jun 1
$133 total
May 31 - Jun 1
Total with taxes and fees
9.6/10 Exceptional! (1,003 reviews)
"The rooms are exceptionally clean, spacious and comfortable. Breakfast is delicious and well done. From cold or hot and pastries. The decor of the entire hotel is outstanding with attention to detail like no other. Individual sitting areas for couples or groups all throughout the hotel. If I were ..."

Reviewed on May 20, 2026

Essenhaus Inn & Conference Center
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
$126 nightly
The price is $141 total per night from May 31 to Jun 1
$141 total
May 31 - Jun 1
Total with taxes and fees
8.2/10 Very Good! (1,000 reviews)
"It just felt dirty, would not stay here again"

Reviewed on May 19, 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 24 to May 25
$187 total
May 24 - May 25
Total with taxes and fees
10/10 Exceptional! (51 reviews)
"This home was even more than we expected. It was clean, nicely decorated, such a cozy and welcoming feel. The kitchen was very well stocked with small appliances and anything you would need. The host greeted us shortly after we arrived and he was very pleasant and answered any questions we had. I ..."

Reviewed on May 18, 2026

Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
See all 581 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

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Frequently asked questions

How much does a Middlebury vacation package cost?
You can pick up a vacation package to this destination from $471 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.

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