Middlebury Vacations from $633

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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.
Doubletree Hotel South Bend

Doubletree Hotel South Bend

4 out of 5
Downtown South Bend
Price was $840, price is now $633 per person
$633
per person
Dec 26 - Dec 31
found 19 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to South Bend (SBN)
7.6/10 Good! (1,015 reviews)
Room was OK but the fitness center needs a major renovation- smelled as if a homeless person was living there for weeks.

Reviewed on Oct 20, 2025

Ivy Court Inn & Suites

Ivy Court Inn & Suites

2.5 out of 5
Price was $871, price is now $646 per person
$646
per person
Dec 26 - Dec 31
found 19 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to South Bend (SBN)
9.2/10 Wonderful! (1,011 reviews)
Perfect stay if you want to be close to ND. Breakfast was outstanding!

Reviewed on Oct 14, 2025

The Inn at Saint Mary's

The Inn at Saint Mary's

3.5 out of 5
Save 100% on your flight
Price was $1,711, price is now $1,334 per person
$1,334
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip flight included
Detroit (DTT) to South Bend (SBN)
9.4/10 Exceptional! (1,025 reviews)
My daughter and I had a great stay! The room was clean. The building/area was quiet. And breakfast was great!

Reviewed on Oct 19, 2025

La Quinta Inn & Suites by Wyndham South Bend

La Quinta Inn & Suites by Wyndham South Bend

3 out of 5
Price was $841, price is now $660 per person
$660
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip flight included
Detroit (DTT) to South Bend (SBN)
7.4/10 Good! (1,003 reviews)
An overall very decent hotel that was perfect for game weekend! Breakfast was perfect!

Reviewed on Oct 21, 2025

Larkspur Landing South Bend

Larkspur Landing South Bend

2.5 out of 5
Price was $908, price is now $718 per person
$718
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip flight included
Detroit (DTT) to South Bend (SBN)
7.8/10 Good! (1,015 reviews)
Great stay for a ND game. Hotel is in process of renovations, but rooms are large and hotel was quiet. Staff provided excellent service and attitude. I would recommend and stay again if I'm ever in South Bend.

Reviewed on Oct 13, 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

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
$95 nightly
The price is $107 total per night from Nov 2 to Nov 3
$107 total
Nov 2 - Nov 3
Total with taxes and fees
8.2/10 Very Good! (1,010 reviews)
The room was mostly clean, however on the lower part of the mirror frame in the bathroom i noticed dried crusty stuff, not sure it was, but it didn't look good. We also had a wasp in our room that was unexpected and kinda upsetting

Reviewed on Oct 18, 2025

Hampton Inn & Suites Middlebury
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 Nov 16 to Nov 17
$122 total
Nov 16 - Nov 17
Total with taxes and fees
9.6/10 Exceptional! (1,024 reviews)
Clean and quiet room! Breakfast was very good. Staff very nice!

Reviewed on Oct 20, 2025

Essenhaus Inn & Conference Center
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

2 out of 5
Middlebury
$135 nightly
The price is $144 total per night from Oct 26 to Oct 27
$144 total
Oct 26 - Oct 27
Total with taxes and fees
9.8/10 Exceptional! (38 reviews)
Very nice place a little into the countryside. Will definitely stay again next time I’m in the area.

Reviewed on Oct 20, 2025

Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
See all 544 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 $633 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.