Middlebury Vacations from $337

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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.
Hilton Vacation Club Varsity Club South Bend, IN

Hilton Vacation Club Varsity Club South Bend, IN

3 out of 5
Price was $407, price is now $337 per person
$337
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
Knoxville (TYS) to South Bend (SBN)
19.2/10 Exceptional! (1,003 reviews)
I did not get the breakfast. Only thing I would suggest is maybe a wall clock in the Hot Tub room. Nice facility.

Reviewed on Nov 21, 2025

Doubletree Hotel South Bend

Doubletree Hotel South Bend

4 out of 5
Downtown South Bend
Price was $537, price is now $363 per person
$363
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
Knoxville (TYS) to South Bend (SBN)
15.2/10 Exceptional! (1,001 reviews)
Staff was excellent

Reviewed on Nov 12, 2025

Morris Inn

Morris Inn

4 out of 5
Price was $722, price is now $528 per person
$528
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
Knoxville (TYS) to South Bend (SBN)
20/10 Exceptional! (1,001 reviews)
The lobby was crowded with students, there was never anywhere to sit despite being paid customers. While I understand the Mo Inn lobby is considered the campus living room, but it is extremely disrespectful to not consider paying guests as part of this "living room" experience. It is highly unlikely I will stay at the Mo Inn in the future.

Reviewed on Nov 17, 2025

The Inn at Saint Mary's

The Inn at Saint Mary's

3.5 out of 5
Price was $660, price is now $519 per person
$519
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
Knoxville (TYS) to South Bend (SBN)
19.2/10 Exceptional! (1,064 reviews)
Room was very clean and staff was welcoming and cheerful!

Reviewed on Nov 21, 2025

Embassy Suites by Hilton South Bend at Notre Dame

Embassy Suites by Hilton South Bend at Notre Dame

3.5 out of 5
Price was $931, price is now $735 per person
$735
per person
Jan 23 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
Knoxville (TYS) to South Bend (SBN)
18.4/10 Exceptional! (679 reviews)
Clean, safe and great location.

Reviewed on Oct 29, 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

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 $337 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.