Middlebury Vacations from $572
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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.
Hotel O Daylight Inn Elkhart I-90, In
$572
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Las Vegas (LAS) to South Bend (SBN)
3.6/10 (163 reviews)
This was a really disappointing experience. Our son needed a one-week stay in the area, and we booked this hotel for him that afternoon. As soon as he checked into his room, he called us to say it was infested with cockroaches.
He went straight to the front desk, explained the situation, and asked for a refund because, honestly, who would stay in a room full of bugs? Instead, he was told he would still be charged for the first night, even though he left immediately.
He found another nearby hotel that was clean and bug-free. I understand hotels have policies, but charging a guest after giving them a room with a cockroach infestation is simply not right.
Reviewed on Aug 2, 2026
Stay near popular Middlebury attractions
Stone Lake
This spring-fed Indiana lake offers pristine waters for fishing enthusiasts seeking bass and bluegill. Enjoy a peaceful morning paddle across its reflective surface where motorboats maintain respectful speeds.
Deutsch Kase Haus
9.2/10 (39 reviews)
This family-owned cheese factory showcased award-winning Colby and Colby-Jack varieties through viewing windows. Visitors could sample fresh cheese curds and browse Amish-made products in its rustic setting.
Meadow Valley Golf Club
Set amid Indiana's Amish countryside, Meadow Valley Golf Club challenges players with undulating greens and strategic water hazards. Reserve an early tee time to experience the tranquil beauty of this top-ranked course.
East Lake
Commune with nature and explore the great outdoors at East Lake during your travels in Middlebury. While in this family-friendly area, you can enjoy the restaurants.
Middlebury Public Library
The Middlebury Public Library offers more than books—it's a community hub with unique lending items like telescopes and museum passes. Browse their collection or join one of their engaging programs for all ages.
Middlebury Community Historical
You can spend an afternoon studying the exhibits at Middlebury Community Historical in Middlebury. While in this family-friendly area, you can enjoy the restaurants.
Hunter Lake
Hunter Lake offers a peaceful retreat for fishing and boating, surrounded by lush Indiana greenery. Pack a picnic to enjoy by the tranquil shoreline while watching local wildlife in their natural habitat.
Memorial Park
Memorial Park honors veterans with its WWII memorial, band shell, and charming gazebo. Enjoy the serene grounds during community festivals or bring a picnic to experience small-town Indiana at its finest.
Middlebury Hotel Deals
Essenhaus Inn & Conference Center
240 Hwy 20 Middlebury IN
Fully refundableReserve now, pay when you stay
$119 nightly
$133 total
Aug 16 - Aug 17
Total with taxes and fees
9.6/10 Exceptional! (1,023 reviews)
"I was looking for a peaceful environment and my stay was just that."
Reviewed on Aug 10, 2026
Hampton Inn & Suites Middlebury
105 Crystal Heights Blvd Middlebury IN
$115 nightly
$129 total
Aug 31 - Sep 1
Total with taxes and fees
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
Middlebury IN
$177 nightly
$189 total
Aug 16 - Aug 17
Total with taxes and fees
10/10 Exceptional! (64 reviews)
"Very clean throughout house. It was great to see the horses in the fenced in area behind house."
Reviewed on Aug 5, 2026
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 $572 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.
