Middlebury Vacations from $415

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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.
Ivy Court Inn & Suites

Ivy Court Inn & Suites

2.5 out of 5
Price was $693, price is now $415 per person
$415
per person
Mar 11 - Mar 16
found 2 hours ago
Roundtrip non-stop flight included
Norfolk (ORF) to South Bend (SBN)
9.2/10 Wonderful! (1,002 reviews)
not bad close to school

Reviewed on Nov 27, 2025

Doubletree Hotel South Bend

Doubletree Hotel South Bend

4 out of 5
Downtown South Bend
Price was $635, price is now $447 per person
$447
per person
Mar 11 - Mar 16
found 2 hours ago
Roundtrip non-stop flight included
Norfolk (ORF) to South Bend (SBN)
7.6/10 Good! (1,001 reviews)
Everything was nice except for the resturant part because there was no heat so we had to somewhere else but besides that and the pool being closed its a 10/10 hotel really nice for a getaway trip.

Reviewed on Jan 8, 2026

The Inn at Saint Mary's

The Inn at Saint Mary's

3.5 out of 5
Price was $802, price is now $588 per person
$588
per person
Mar 11 - Mar 16
found 2 hours ago
Roundtrip non-stop flight included
Norfolk (ORF) to South Bend (SBN)
9.6/10 Exceptional! (1,064 reviews)
I used a Tesla destination charger. One port was broken and the other one was not stable. So I used other general EV chargers. They are free of charge.

Reviewed on Jan 4, 2026

Residence Inn by Marriott South Bend Mishawaka

Residence Inn by Marriott South Bend Mishawaka

3 out of 5
Price was $614, price is now $507 per person
$507
per person
Mar 11 - Mar 16
found 2 hours ago
Roundtrip non-stop flight included
Norfolk (ORF) to South Bend (SBN)
9/10 Wonderful! (423 reviews)
Always a great stay

Reviewed on Dec 10, 2025

Courtyard by Marriott South Bend Downtown

Courtyard by Marriott South Bend Downtown

3 out of 5
Downtown South Bend
Price was $742, price is now $619 per person
$619
per person
Mar 11 - Mar 16
found 2 hours ago
Roundtrip non-stop flight included
Norfolk (ORF) to South Bend (SBN)
8.8/10 Excellent! (374 reviews)
It was easy to navigate. Was on the pricier side due to the ND game. Would return. Only suggestion is change the bathrooms. The one glass door concept isn’t pleasing and tends to flood the bathroom. Also the rusty soap tray wasn’t necessary in the shower.

Reviewed on Nov 23, 2025

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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 Jan 11 to Jan 12
$122 total
Jan 11 - Jan 12
Total with taxes and fees
9.6/10 Exceptional! (1,007 reviews)
Everything. The room decor, the cleanliness and the kind staff. Breakfast was amazing and very flavorful. We will always aim to stay here, it makes us feel like home.

Reviewed on Jan 4, 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 Jan 18 to Jan 19
$123 total
Jan 18 - Jan 19
Total with taxes and fees
8.2/10 Very Good! (1,006 reviews)
Excellent staff from the desk to breakfast personal ,very good hot breakfast,clean confortable room. Nice pool with hot tub and reasonable rates for stay

Reviewed on Dec 31, 2025

Hampton Inn & Suites Middlebury
The Back Porch Haven Stay in Amish Country yet close to Notre Dame

The Back Porch Haven Stay in Amish Country yet close to Notre Dame

Middlebury IN
$310 nightly
The price is $331 total per night from Jan 9 to Jan 10
$331 total
Jan 9 - Jan 10
Total with taxes and fees
9.8/10 Exceptional! (26 reviews)
Quirky property. That isn’t a bad thing just expect to take a step back in time. Property was very clean. Beds weren’t very comfortable but they rarely are away from home. The garage door opener needs updating and can be fussy. Very quiet. Great location if doing business at Grand Design RV.

Reviewed on Dec 1, 2025

The Back Porch Haven Stay in Amish Country yet close to Notre Dame
See all 567 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 $415 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.