Middlebury Holidays
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- Better togetherSave up to S$1,300 when you book a flight and hotel together*
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Top hotels in Middlebury
Essenhaus Inn & Conference Center
240 Hwy 20 Middlebury IN
Fully refundableReserve now, pay when you stay
S$153
16 Aug - 17 Aug
includes taxes & fees
9.6/10 Exceptional! (1,018 reviews)
"Great stay! Super helpful at check-in, room was excellent clean and check-out was super easy. Would stay here again without hesitation!"
Reviewed on 9 Aug, 2026
Hampton Inn & Suites Middlebury
105 Crystal Heights Blvd Middlebury IN
S$168
24 Aug - 25 Aug
includes taxes & fees
Farmstead Inn & Conference Center
370 S Van Buren St Shipshewana IN
Fully refundableReserve now, pay when you stay
S$193
23 Aug - 24 Aug
includes taxes & fees
9.6/10 Exceptional! (1,121 reviews)
"First time staying here. Spacious room and great walk- shower. Everyone at the front desk polite and helpful.close to town and places to eat ."
Reviewed on 8 Aug, 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.
Stay near popular Middlebury attractions
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.
Deutsch Kase Haus
9.2/10 (39 reviews)
This family-owned cheese factory showcased award-winning Colby and Colby-Jack varieties through viewing windows. Visitors could sample fresh cheese curds and browse Amish-made products in its rustic setting.
Meadow Valley Golf Club
Set amid Indiana's Amish countryside, Meadow Valley Golf Club challenges players with undulating greens and strategic water hazards. Reserve an early tee time to experience the tranquil beauty of this top-ranked course.
East Lake
Commune with nature and explore the great outdoors at East Lake during your travels in Middlebury. While in this family-friendly area, you can enjoy the restaurants.
Hunter Lake
Hunter Lake offers a peaceful retreat for fishing and boating, surrounded by lush Indiana greenery. Pack a picnic to enjoy by the tranquil shoreline while watching local wildlife in their natural habitat.
Middlebury Public Library
The Middlebury Public Library offers more than books—it's a community hub with unique lending items like telescopes and museum passes. Browse their collection or join one of their engaging programmes for all ages.
Middlebury Community Historical
You can spend an afternoon browsing the exhibits at Middlebury Community Historical during your trip to Middlebury. While in this family-friendly area, you can enjoy the restaurants.
Memorial Park
Memorial Park honours veterans with its WWII memorial, band shell, and charming gazebo. Enjoy the serene grounds during community festivals or bring a picnic to experience small-town Indiana at its finest.
Frequently asked questions
How much does a Middlebury holiday package cost?
You can pick up a holiday package to this destination on Expedia. However, how much your holiday 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 score a cheap Middlebury holiday package, consider planning a trip in January, February and November. You'll generally find better rates on airfares and hotels during these quieter months — ideal for budget-conscious travellers.
How many days is enough for Middlebury?
The ideal length for your Middlebury holiday depends on what you'd like to see. Generally, a handful of days to a week will give you time to check out all the main sights and discover some hidden gems 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 holiday package well in advance.
Is it cheaper to book a Middlebury holiday as a package?
You can enjoy significant savings on your next Middlebury getaway by booking a tailored holiday 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 holiday 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.
How to plan a trip to Middlebury?
- Choose the ideal time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to visit Middlebury.
- Calculate your budget: Make sure you have enough money to pay for everything from transportation and food to activities and airfares. Your accommodation will likely be the largest expense during your trip to Middlebury.
- Decide how long to go for: Now that you know more about Middlebury, you can work out the ideal length of your break. Create a draft plan and allocate enough time to cover everything you want to see.
- Bundle your airfare and accommodation: Once you've settled on your dates and duration, lock in the perfect Middlebury holiday package for you.
* 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.
