Middlebury Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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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.

Ready to book your vacation to Middlebury?

 

Choose your dates

Middlebury Hotel Deals

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
The price is CA $150 per night from Aug 17 to Aug 18
CA $150
CA $168 total
Aug 17 - Aug 18
includes taxes & fees
8.2/10 Very Good! (1,007 reviews)
"Easy to find. Nice area."

Reviewed on Aug. 3, 2025

Hampton Inn & Suites Middlebury
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
The price is CA $148 per night from Aug 10 to Aug 11
CA $148
CA $165 total
Aug 10 - Aug 11
includes taxes & fees
9.6/10 Exceptional! (1,006 reviews)
"Staff were amazing. When I booked with Expedia the room said it had a balcony which was why I chose that room. When we were given room it did not have one. I spoke with ladies at desk and they said that was Expedia error but they worked their magic and moved us to a balcony room. So kind and accommodating. ..."

Reviewed on Aug. 4, 2025

Essenhaus Inn & Conference Center
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury

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

2 out of 5
Middlebury
The price is CA $158 per night from Sep 7 to Sep 8
CA $158
CA $198 total
Sep 7 - Sep 8
includes taxes & fees
10/10 Exceptional! (22 reviews)
Birthday/concert getaway weekend
"This quaint little cottage is perfect for a quiet stay in the country. I can't say enough about it. Mike and his wife is the best!!!"

Reviewed on Aug. 2, 2025

Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
See all 530 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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 many days is enough for Middlebury?
With a well-planned schedule, you can easily tick off the main Middlebury attractions in a few days. But if you prefer to discover lesser-known spots or take day trips, think about booking your Middlebury vacation for longer.
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 travelling 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.