
Middlebury Holidays
Photo by Ann Sair
- Plan, book, travel with confidence
Better together
Save up to S$134 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Top hotels in Middlebury

Hampton Inn & Suites Middlebury
105 Crystal Heights Blvd, Middlebury, IN
Fully refundableReserve now, pay when you stay
The price is S$151 per night from 3 Aug to 4 Aug
S$151
3 Aug - 4 Aug
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
Just average
"The TV was hard to work at first The bed and pillows were terrible The sound from above us was awful"
Reviewed on 6 Jul, 2025

Essenhaus Inn & Conference Center
240 Hwy 20, Middlebury, IN
Fully refundableReserve now, pay when you stay
9.6/10 Exceptional! (1,003 reviews)
"We were not able to make phone calls on our cell phones in the room. We both got messages that we could only make emergency calls. I went outside through the pool area early this morning in order to make a call. Breakfast food items were good, but we were disappointed that there was not a hot egg ..."
Reviewed on 3 Jul, 2025

Farmstead Inn & Conference Center
370 S Van Buren St, Shipshewana, IN
Fully refundableReserve now, pay when you stay
9.6/10 Exceptional! (1,003 reviews)
"Very clean facility. Delicious breakfast. Would definitely stay here again!"
Reviewed on 4 Jul, 2025
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.
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.