Middlebury Vacations from $339

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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 $374, price is now $339 per person
$339
per person
Apr 24 - Apr 26
found 21 hours ago
Roundtrip flight included
Washington (IAD) to South Bend (SBN)
6.8/10 (804 reviews)
The room was in good condition with cleanliness. However, there were 4 of us and only two towels and no conditioner. Also, we arrived to hotel around 4pm and couldn't get into room until a little after 5pm. We were given pool access while we waited.

Reviewed on Mar 1, 2026

Larkspur Landing South Bend

Larkspur Landing South Bend

2.5 out of 5
Price was $568, price is now $488 per person
$488
per person
May 29 - May 31
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to South Bend (SBN)
7.8/10 Good! (1,001 reviews)
Courteous staff, comfortable bed.

Reviewed on Mar 1, 2026

Doubletree Hotel South Bend

Doubletree Hotel South Bend

4 out of 5
Downtown South Bend
Price was $743, price is now $660 per person
$660
per person
May 29 - May 31
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to South Bend (SBN)
7.6/10 Good! (1,001 reviews)
Under construction was annoying. The sound when taking a nap, debris in hallways.

Reviewed on Feb 27, 2026

The Inn at Saint Mary's

The Inn at Saint Mary's

3.5 out of 5
Price was $645, price is now $578 per person
$578
per person
May 29 - May 31
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to South Bend (SBN)
9.6/10 Exceptional! (1,064 reviews)
Very quick check in. Room was ready. Hotel was under construction, but still comfortable.

Reviewed on Feb 26, 2026

Four Winds Casino South Bend

Four Winds Casino South Bend

3 out of 5
Price was $753, price is now $685 per person
$685
per person
Apr 24 - Apr 26
found 21 hours ago
Roundtrip flight included
Washington (IAD) to South Bend (SBN)
9.6/10 Exceptional! (703 reviews)
It's a beautiful facility. Staff and patrons were friendly and polite. The room was clean. We enjoyed breakfast at the Edgewater Cafe. For being relatively new, the mattresses lacked supportive edges and in fact sagged where guests sit at the edges. Getting permission to check in past 9:00 p.m. was also inconvenient. Otherwise we had a nice visit.

Reviewed on Mar 1, 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 Mar 8 to Mar 9
$122 total
Mar 8 - Mar 9
Total with taxes and fees
9.6/10 Exceptional! (1,001 reviews)
yes

Reviewed on Feb 22, 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
$108 nightly
The price is $121 total per night from Mar 30 to Mar 31
$121 total
Mar 30 - Mar 31
Total with taxes and fees
8.4/10 Very Good! (1,004 reviews)
Great

Reviewed on Mar 1, 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)
Had a great time

Reviewed on Oct 28, 2025

Get rates
Amazing view of Stone Lake from top deck. Thirty five miles from Notre Dame.
See all 564 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 $339 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.