Middlebury Vacations from $703
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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.
Studio 6 Elkhart, IN- Kitchenette Rooms
$1,061
per person
Nov 13 - Nov 15
found 1 day ago
Roundtrip flight included
Allentown (ABE) to South Bend (SBN)
6/10 (97 reviews)
Mi estancia en el hotel fue aceptable, aunque con varios puntos que podrían mejorar. La ubicación es conveniente y el personal, en general, muestra buena disposición para ayudar, aunque a veces parecen sobrecargados y tardan en atender.
Reviewed on Oct 1, 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.
Brokesha Lake
Commune with nature and explore the great outdoors at Brokesha Lake during your travels in Middlebury. While in this family-friendly area, you can enjoy the restaurants.
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.
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.
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.
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.
Riverbend Park
Meander along the mile-long trail of Riverbend Park, where the Little Elkhart River creates a tranquil backdrop. Bring binoculars for bird watching from the fishing pier or relax at the nature-themed playground.
Corson Riverwoods County Park
This unique park features a Pollinator Playpath with interactive areas themed around butterflies and bees. Explore giant caterpillar structures and honeycomb hideouts while learning about these essential creatures.
Middlebury Hotel Deals
Essenhaus Inn & Conference Center
240 Hwy 20 Middlebury IN
Fully refundableReserve now, pay when you stay
$101 nightly
$113 total
Oct 4 - Oct 5
Total with taxes and fees
9.6/10 Exceptional! (1,004 reviews)
"No complaints at all. everything was as it should be. This is an American owned and operated resort and they know how to look after their guests. Everyone was polite and courteous and the stay was perfect. We are repeat guests and will continue staying with them"
Reviewed on Oct 2, 2026
Hampton Inn & Suites Middlebury
105 Crystal Heights Blvd Middlebury IN
Fully refundableReserve now, pay when you stay
$107 nightly
$120 total
Oct 17 - Oct 18
Total with taxes and fees
8.2/10 Very Good! (1,002 reviews)
"Had a handicap room that was not accessible to me. No grab bar by the toilet and the toilet was too low for a handicap person to get up from. Asked for a new room, request was denied. We were on the 3rd floor and I had to go down the elevator and use the lobby restroom, which did have a grab bar ..."
Reviewed on Oct 3, 2026
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
Middlebury IN
$176 nightly
$188 total
Oct 4 - Oct 5
Total with taxes and fees
10/10 Exceptional! (71 reviews)
"House was very cute and clean. The host was very responsive . Parking was convenient right by the door. The kitchen was stocked well. We would stay here again."
Reviewed on Sep 30, 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 $703 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.
