Middlebury Vacations from $1,873

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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.
Remodeled Home 1 Mile From Notre Dame 1150

Remodeled Home 1 Mile From Notre Dame 1150

2 out of 5
Save 100% on your flight
Price was $2,347, price is now $1,873 per person
$1,873
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to South Bend (SBN)
No reviews
Brand New Luxury Townhouse Steps To Notre Dame Fire Place Fire pit 1418

Brand New Luxury Townhouse Steps To Notre Dame Fire Place Fire pit 1418

2 out of 5
Wooded Estates
Save 100% on your flight
Price was $6,138, price is now $4,753 per person
$4,753
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Harrisburg (MDT) to South Bend (SBN)
No reviews
10 min Walk to ND Stadium 1820

10 min Walk to ND Stadium 1820

2 out of 5
Save 100% on your flight
Price was $2,660, price is now $2,109 per person
$2,109
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to South Bend (SBN)
No reviews
2 Blocks to ND 4 Bedroom 2 Bath Home 1217

2 Blocks to ND 4 Bedroom 2 Bath Home 1217

2 out of 5
Wooded Estates
Save 100% on your flight
Price was $2,431, price is now $1,945 per person
$1,945
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Harrisburg (MDT) to South Bend (SBN)
No reviews
Modern Home Just 10 Mins to Notre Dame 18384

Modern Home Just 10 Mins to Notre Dame 18384

2 out of 5
Save 100% on your flight
Price was $2,431, price is now $1,945 per person
$1,945
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Harrisburg (MDT) to South Bend (SBN)
No reviews
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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
$106 nightly
The price is $118 total per night from Sep 14 to Sep 15
$118 total
Sep 14 - Sep 15
Total with taxes and fees
8.2/10 Very Good! (1,003 reviews)
"We were surprised with an upgrade room that included a jacuzzi tub for 2, unfortunately the room had a foul odor coming from the drain. The mgr did come to make the air freshener in the room was working, which it was but the odor was still there. They didn’t offer us a different room(I didn’t ask ..."

Reviewed on Aug 22, 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
$129 nightly
The price is $144 total per night from Sep 7 to Sep 8
$144 total
Sep 7 - Sep 8
Total with taxes and fees
9.6/10 Exceptional! (1,005 reviews)
Favorite place to stay!
"Our favorite place to stay when we visit the area, and we have stayed at several. Everyone is friendly and helpful. Rooms are comfortable, breakfast is good."

Reviewed on Aug 24, 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 Aug 28 to Aug 29
$144 total
Aug 28 - Aug 29
Total with taxes and fees
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
See all 521 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.

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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 $1,873 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.