Middlebury Vacations from $333

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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.
Staybridge Suites Elkhart by IHG

Staybridge Suites Elkhart by IHG

3 out of 5
Price was $405, price is now $333 per person
$333
per person
Feb 18 - Feb 21
found 10 hours ago
Roundtrip non-stop flight included
Greenville (GSP) to South Bend (SBN)
8.8/10 Excellent! (580 reviews)
Everything was good.

Reviewed on Dec 8, 2025

Ivy Court Inn & Suites

Ivy Court Inn & Suites

2.5 out of 5
Save 100% on your flight
Price was $690, price is now $402 per person
$402
per person
Feb 18 - Feb 21
found 10 hours ago
Roundtrip non-stop flight included
Greenville (GSP) to South Bend (SBN)
9.2/10 Wonderful! (1,002 reviews)
not bad close to school

Reviewed on Nov 27, 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 $1,007, price is now $697 per person
$697
per person
Feb 18 - Feb 21
found 10 hours ago
Roundtrip non-stop flight included
Greenville (GSP) to South Bend (SBN)
9.6/10 Exceptional! (1,064 reviews)
Staff was courteous. Room was clean and comfortable. Buffet breakfast was nice and had plenty to choose from.

Reviewed on Dec 17, 2025

Doubletree Hotel South Bend

Doubletree Hotel South Bend

4 out of 5
Downtown South Bend
Price was $505, price is now $356 per person
$356
per person
Feb 18 - Feb 21
found 10 hours ago
Roundtrip non-stop flight included
Greenville (GSP) to South Bend (SBN)
7.6/10 Good! (1,001 reviews)
The room was absolutely amazing, the view was breathtaking, and the atmosphere within the entire hotel made it feel as if it were a city within the city. Absolutely amazing! I wish there were a free continental breakfast as well, and a bathtub shower combo instead of a shower with a door that kept opening, but otherwise a phenomenal experience! May consider checking in again!

Reviewed on Dec 15, 2025

Residence Inn by Marriott South Bend Mishawaka

Residence Inn by Marriott South Bend Mishawaka

3 out of 5
Price was $454, price is now $377 per person
$377
per person
Jan 23 - Jan 26
found 10 hours ago
Roundtrip non-stop flight included
Greenville (GSP) to South Bend (SBN)
9/10 Wonderful! (423 reviews)
Always a great stay

Reviewed on Dec 10, 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
$110 nightly
The price is $123 total per night from Jan 4 to Jan 5
$123 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.2/10 Very Good! (1,000 reviews)
Our room was clean and very nice!

Reviewed on Dec 9, 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 Jan 4 to Jan 5
$122 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9.6/10 Exceptional! (1,003 reviews)
Shower head was terrible. Upgrade needed. Couldn’t close a curtain, because it was off the rod. Night light bulb was burned out. I left a note with housekeeping, but neglected to mention the shower head.

Reviewed on Dec 7, 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 IN
$135 nightly
The price is $144 total per night from Dec 21 to Dec 22
$144 total
Dec 21 - Dec 22
Total with taxes and fees
9.8/10 Exceptional! (41 reviews)
Very nice area in the country. It was nice to see the horses. The place was very clean. All you need to bring is food.

Reviewed on Dec 13, 2025

Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
See all 560 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 $333 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.