Middlebury Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Middlebury Hotel Deals
Essenhaus Inn & Conference Center
240 Hwy 20 Middlebury IN
Fully refundableReserve now, pay when you stay
The price is CA $148 per night from May 31 to Jun 1
CA $148
CA $166 total
May 31 - Jun 1
includes taxes & fees
9.6/10 Exceptional! (1,004 reviews)
"Very clean and neat facility. Room was excellent with good air conditioning and clean bathroom. Quality of the bathroom and fixtures was excellent. Restaurant on property was also outstanding."
Reviewed on May 21, 2026
Hampton Inn & Suites Middlebury
105 Crystal Heights Blvd Middlebury IN
The price is CA $174 per night from May 31 to Jun 1
CA $174
CA $195 total
May 31 - Jun 1
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
"Location is excellent!"
Reviewed on May 23, 2026
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
Middlebury IN
The price is CA $214 per night from May 28 to May 29
CA $214
CA $262 total
May 28 - May 29
includes taxes & fees
10/10 Exceptional! (51 reviews)
"This home was even more than we expected. It was clean, nicely decorated, such a cozy and welcoming feel. The kitchen was very well stocked with small appliances and anything you would need. The host greeted us shortly after we arrived and he was very pleasant and answered any questions we had. I ..."
Reviewed on May 18, 2026
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.
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.
