Middlebury Vacations from $493

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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.
Hotel O Daylight Inn Elkhart I-90, In

Hotel O Daylight Inn Elkhart I-90, In

2.5 out of 5
Price was $526, price is now $493 per person
$493
per person
Dec 17 - Dec 20
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to South Bend (SBN)
3.6/10 (183 reviews)
We were welcomed by a pungent smell when we opened the door. The sheets and bedspread were dirty. There was a huge stain on the lampshade. There were dead bugs along the floor board of the bathroom. I guess an upside were they were dead. The fire alarm was chirping from the battery being low and the front desk was not helpful in wanting to replace it. It was so bad we choose to leave without staying. I thought I could sleep anywhere for 5 hours but I was wrong!

Reviewed on Nov 10, 2026

Days Inn by Wyndham South Bend / Notre Dame

Days Inn by Wyndham South Bend / Notre Dame

2 out of 5
Price was $954, price is now $893 per person
$893
per person
Dec 17 - Dec 20
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to South Bend (SBN)
7/10 Good! (1,000 reviews)
Raised the rates for the football game. Don’t offer breakfast

Reviewed on Nov 11, 2026

Indy Escape Sauna Hot Tub Firepit Games

Indy Escape Sauna Hot Tub Firepit Games

2 out of 5
Price was $2,416, price is now $2,294 per person
$2,294
per person
Dec 17 - Dec 20
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to South Bend (SBN)
No reviews

Sunset Dunes Vacation Villas

Sunset Dunes Vacation Villas

3 out of 5
Price was $613, price is now $591 per person
$591
per person
Dec 17 - Dec 20
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to South Bend (SBN)
9.4/10 Exceptional! (40 reviews)
Location was great! 10 minute walk to the lake and easy access off the highway.

Reviewed on Nov 10, 2026

Van Buren Hotel

Van Buren Hotel

4 out of 5
Price was $668, price is now $650 per person
$650
per person
Dec 17 - Dec 20
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to South Bend (SBN)
9.2/10 Wonderful! (1,567 reviews)

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Stay near popular Middlebury attractions

A calm lake with three white geese swimming near the shore, surrounded by rocks and trees.

Stone Lake

This spring-fed Indiana lake offers pristine waters for fishing enthusiasts seeking bass and bluegill. Enjoy a peaceful morning paddle across its reflective surface where motorboats maintain respectful speeds.
See properties

Middlebury Hotel Deals

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
$119 nightly
The price is $133 total per night from Nov 15 to Nov 16
$133 total
Nov 15 - Nov 16
Total with taxes and fees
9.6/10 Exceptional! (1,002 reviews)
"Great place clean and perfect location."

Reviewed on Nov 12, 2026

Essenhaus Inn & Conference Center
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
$114 nightly
The price is $128 total per night from Nov 22 to Nov 23
$128 total
Nov 22 - Nov 23
Total with taxes and fees
8.2/10 Very Good! (1,000 reviews)
"Was not informed that the pool, fitness room and breakfast area's were ALL under construction and not available for use. The bag breakfast was sad, with soggy bagels. Out side lightening in the parking lot was dangerously poor, half the hacker lot had no lights."

Reviewed on Nov 5, 2026

Hampton Inn & Suites Middlebury
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

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

Middlebury IN
$184 nightly
The price is $197 total per night from Nov 15 to Nov 16
$197 total
Nov 15 - Nov 16
Total with taxes and fees
10/10 Exceptional! (77 reviews)
"Cozy and quaint getaway for relaxing and a quiet night's sleep after shopping and shows in Amish Country."

Reviewed on Nov 8, 2026

Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
See all 605 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 $493 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.