Middlebury Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AEDĀ 5,000 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

Find the Best Middlebury Vacation Packages

Middlebury Hotel Deals

Essenhaus Inn & Conference Center

Essenhaus Inn & Conference Center

3.5 out of 5
240 Hwy 20 Middlebury IN
The price is AEDĀ 393 per night from Aug 9 to Aug 10
AEDĀ 393
AEDĀ 441 total
9 Aug - 10 Aug
includes taxes & fees
9.6/10 Exceptional! (1,011 reviews)
"The dinner reservation was clutch. Breakfast awesome. The resort, fantastic as always"

Reviewed on 26 July 2026

Essenhaus Inn & Conference Center
Hampton Inn & Suites Middlebury

Hampton Inn & Suites Middlebury

2.5 out of 5
105 Crystal Heights Blvd Middlebury IN
The price is AEDĀ 388 per night from Aug 24 to Aug 25
AEDĀ 388
AEDĀ 434 total
24 Aug - 25 Aug
includes taxes & fees
8.2/10 Very Good! (1,004 reviews)
"The "heated pool" surely was not heated!The pool was very cold! Stayed for 2 days and housekeeping did not do such a good job vacuuming the 2nd day. The breakfast was good. Did not have an alarm clock in the room as usually hotels do.The front desk employees were very nice and friendly. Definitely ..."

Reviewed on 27 July 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
The price is AEDĀ 569 per night from Aug 2 to Aug 3
AEDĀ 569
AEDĀ 700 total
2 Aug - 3 Aug
includes taxes & fees
10/10 Exceptional! (60 reviews)
"Loved the little house conveniently located just outside the main drag about 12 minutes away."

Reviewed on 20 July 2026

Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
See all 592 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.

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.
See properties

Frequently asked questions

How much does a Middlebury vacation package cost?
Offering excellent value package deals on Expedia, you'll be pleasantly surprised at how much a vacation to Middlebury costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Middlebury?
January, February and November are great times to search for cheap Middlebury vacation packages. Choosing to travel in quieter months means you can generally find lower prices on flights and accommodations.
How to find the best Middlebury package deals?
Landing a cheap Middlebury package deal is easy with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your budget range, apply a few filters and browse what's available. You can tailor your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most wallet-friendly Middlebury package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are generally lower.
Is it cheaper to book a Middlebury vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking flights and hotels separately. Better still, you can tailor your Middlebury getaway to match your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Middlebury?
If you're planning an impromptu Middlebury getaway, check out our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can land amazing deals on your hotels and flights by booking well in advance.
How to plan a trip to Middlebury?

  1. Choose when to travel: Check your calendar and get packing. Your preferred time of year and the type of activities available will also help you decide when to visit Middlebury.
  2. Set your budget: Consider expenses such as food, flights and transportation when working out how much to save for your trip to Middlebury. Then, choose a property that works with your budget, whether that's a wallet-friendly option or a high-end getaway.
  3. Set the duration of your trip: Start by listing all the sights and activities you'd like to get to in Middlebury. Then, estimate how long you'll need at each, along with any travel time.
  4. Combine your accommodations and airfare: After you've nailed down your dates and duration, lock in the right Middlebury vacation package for you.