Middlebury Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    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.

Top Middlebury Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Baymont by Wyndham Elkhart

Baymont by Wyndham Elkhart

2.5 out of 5
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to South Bend (SBN)
7.2/10 Good! (1,001 reviews)
Was nice and a good price will stay again

Reviewed on Jul. 21, 2025

Baymont by Wyndham Mishawaka South Bend Area

Baymont by Wyndham Mishawaka South Bend Area

2.5 out of 5
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to South Bend (SBN)
7.2/10 Good! (1,001 reviews)
We came for the pool and it was smaller but everyone had a good time.

Reviewed on Jul. 21, 2025

Brand New Luxury Townhouse Steps To Notre Dame Fire Place Fire pit 1418

Brand New Luxury Townhouse Steps To Notre Dame Fire Place Fire pit 1418

2 out of 5
Wooded Estates
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to South Bend (SBN)
No reviews
Historic Renovated Home Steps to Notre Dame 103

Historic Renovated Home Steps to Notre Dame 103

2 out of 5
Northshore Triangle
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to South Bend (SBN)
No reviews
Remodeled Home 1 Mile From Notre Dame 1150

Remodeled Home 1 Mile From Notre Dame 1150

2 out of 5
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to South Bend (SBN)
No reviews

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 $149 per night from Aug 3 to Aug 4
CA $149
CA $167 total
Aug 3 - Aug 4
includes taxes & fees
8.2/10 Very Good! (1,010 reviews)
"The two guys who were on duty at the front desk when we checked in were wonderful. They were welcoming and helpful. Both had a sense of humor which made the experience even more pleasant. Later, when we left for the evening, they both stepped outside with us to guide us with directions to our destination. ..."

Reviewed on Jul. 20, 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 $146 per night from Jul 27 to Jul 28
CA $146
CA $164 total
Jul 27 - Jul 28
includes taxes & fees
9.6/10 Exceptional! (1,013 reviews)
"Everything was great!!"

Reviewed on Jul. 24, 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 $157 per night from Jul 27 to Jul 28
CA $157
CA $197 total
Jul 27 - Jul 28
includes taxes & fees
10/10 Exceptional! (21 reviews)
"Quiet, clean and cozy place. Perfect for our girls’ getaway! Owners were very friendly, responsive and great communication. This is a rural area, so you have to drive to get to the towns in the area but all within 15 minutes. The 2nd bathroom shower is small, but clean and nice. The cottage has AC ..."

Reviewed on Jul. 16, 2025

Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
See all 534 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 from CA $1,003 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.