Middlebury Vacations from $454

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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.
SpringHill Suites by Marriott Mishawaka-University Area

SpringHill Suites by Marriott Mishawaka-University Area

3 out of 5
Price was $556, price is now $454 per person
$454
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to South Bend (SBN)
8.8/10 Excellent! (676 reviews)
Clean dewat atmosphere

Reviewed on Aug 3, 2025

Doubletree Hotel South Bend

Doubletree Hotel South Bend

4 out of 5
Downtown South Bend
Price was $1,059, price is now $793 per person
$793
per person
Nov 20 - Nov 23
found 21 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to South Bend (SBN)
7.6/10 Good! (1,006 reviews)
Things were under repair and disheveled. A lot of the amenities were unavailable and it was understaffed. We did have things addressed quickly by the staff available and they did their best to accommodate us. It’s a cool building

Reviewed on Sep 14, 2025

The Inn at Saint Mary's

The Inn at Saint Mary's

3.5 out of 5
Price was $1,434, price is now $1,159 per person
$1,159
per person
Nov 20 - Nov 23
found 21 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to South Bend (SBN)
9.4/10 Exceptional! (1,022 reviews)
Very clean but bed was kinda hard and for 170$ we had no tv and gave us no discount.

Reviewed on Sep 16, 2025

Motel 6 South Bend, IN - Mishawaka

Motel 6 South Bend, IN - Mishawaka

2 out of 5
Price was $913, price is now $747 per person
$747
per person
Nov 20 - Nov 23
found 21 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to South Bend (SBN)
7/10 Good! (1,016 reviews)
The night staff was EXCEPTIONAL and we felt very welcomed after driving 16 hours.

Reviewed on Sep 13, 2025

La Quinta Inn & Suites by Wyndham South Bend

La Quinta Inn & Suites by Wyndham South Bend

3 out of 5
Price was $1,109, price is now $909 per person
$909
per person
Nov 20 - Nov 23
found 21 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to South Bend (SBN)
7.4/10 Good! (1,004 reviews)
Reserved at the last minute when another local hotel checked us into a room with one bed instead of the two that we needed for 2 people. Vijay, who was working that night was super helpful and solicitous. The hotel was perfectly fine and walking distance to the airport. It was the staff here that made for a great stay.

Reviewed on Sep 15, 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
$98 nightly
The price is $109 total per night from Oct 5 to Oct 6
$109 total
Oct 5 - Oct 6
Total with taxes and fees
8.2/10 Very Good! (1,005 reviews)
"Clean. Friendly staff. Nice location"

Reviewed on Sep 15, 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 21 to Sep 22
$144 total
Sep 21 - Sep 22
Total with taxes and fees
9.6/10 Exceptional! (1,002 reviews)
"Spotless!"

Reviewed on Sep 14, 2025

Essenhaus Inn & Conference Center
Solar powered-Charming 1-Bedroom in Middlebury

Solar powered-Charming 1-Bedroom in Middlebury

Middlebury
$147 nightly
The price is $157 total per night from Sep 18 to Sep 19
$157 total
Sep 18 - Sep 19
Total with taxes and fees
9.6/10 Exceptional! (9 reviews)
Highly recommended!
"Beautiful and peaceful place to stay! So much attention to detail made a difference! Highly recommended!"

Reviewed on Aug 3, 2025

Solar powered-Charming 1-Bedroom in Middlebury
See all 538 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 $454 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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