Middlebury Vacations from $411

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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.
Motel 6 Elkhart, IN

Motel 6 Elkhart, IN

2 out of 5
Price was $459, price is now $411 per person
$411
per person
Apr 18 - Apr 21
found 22 hours ago
Roundtrip non-stop flight included
Miami (MIA) to South Bend (SBN)
5.4/10 (268 reviews)
It was a nice place to stay quite too

Reviewed on Nov 10, 2025

Ivy Court Inn & Suites

Ivy Court Inn & Suites

2.5 out of 5
Price was $511, price is now $443 per person
$443
per person
Mar 27 - Mar 29
found 3 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to South Bend (SBN)
9.2/10 Wonderful! (1,002 reviews)
Vary nice and clean rooms. Friendly staff. Great breakfast.

Reviewed on Jan 23, 2026

Larkspur Landing South Bend

Larkspur Landing South Bend

2.5 out of 5
Price was $520, price is now $454 per person
$454
per person
Mar 27 - Mar 29
found 3 hours ago
Roundtrip non-stop flight included
Philadelphia (PHL) to South Bend (SBN)
7.8/10 Good! (1,001 reviews)
Clean room - Liked the location - Friendly staff - Overall, great stay.

Reviewed on Dec 12, 2025

The Chicken Coop a Modern Riverfront Oasis 908

The Chicken Coop a Modern Riverfront Oasis 908

2 out of 5
Price was $1,224, price is now $1,085 per person
$1,085
per person
Apr 18 - Apr 21
found 22 hours ago
Roundtrip non-stop flight included
Miami (MIA) to South Bend (SBN)
No reviews
Staybridge Suites Elkhart by IHG

Staybridge Suites Elkhart by IHG

3 out of 5
Price was $543, price is now $492 per person
$492
per person
Apr 18 - Apr 21
found 22 hours ago
Roundtrip non-stop flight included
Miami (MIA) to South Bend (SBN)
8.8/10 Excellent! (580 reviews)
Very pleasant stay with a very pleasant staff. Clean, comfortable and affordable. Would stay here again.

Reviewed on Jan 18, 2026

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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
$109 nightly
The price is $122 total per night from Feb 1 to Feb 2
$122 total
Feb 1 - Feb 2
Total with taxes and fees
9.6/10 Exceptional! (1,000 reviews)
Breakfast could be better. Balcony get view. Loved the atrium

Reviewed on Jan 19, 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
$110 nightly
The price is $123 total per night from Feb 15 to Feb 16
$123 total
Feb 15 - Feb 16
Total with taxes and fees
8.2/10 Very Good! (1,003 reviews)
Verygood experiance

Reviewed on Jan 20, 2026

Hampton Inn & Suites Middlebury
Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.

Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.

Middlebury IN
9.6/10 Exceptional! (25 reviews)
We enjoyed the lake house very much with a beautiful view from every room.

Reviewed on Oct 10, 2025

Get rates
Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.
See all 566 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 $411 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.