Middlebury Vacation Packages

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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.
Irish Lodge South Bend

Irish Lodge South Bend

2.5 out of 5
Price was CA $826, price is now CA $740 per person
CA $740
per person
Aug 23 - Aug 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to South Bend (SBN)
7.8/10 Good! (199 reviews)
It was a good place to stay for the night. The bed was comfortable. A nice quick breakfast with variety. I will stay again when I am in town.

Reviewed on Jul 2, 2026

The Inn at Saint Mary's

The Inn at Saint Mary's

3.5 out of 5
Price was CA $1,216, price is now CA $1,007 per person
CA $1,007
per person
Aug 23 - Aug 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to South Bend (SBN)
9.4/10 Exceptional! (1,225 reviews)
I didn't sign up for what I got. The hotel in the photos online looked beautiful and I was really looking forward to it. It may have been beautiful before, and it may be beautiful again one day, but right now it is a big construction zone. It looks like a bomb went off in the lobby. If I knew in advance what was happening, i NEVER would have booked the stay. The room was fine and mostly quiet, but the rest was not fine and not worth it.

Reviewed on Jul 3, 2026

La Quinta Suites by Wyndham South Bend Notre Dame Area

La Quinta Suites by Wyndham South Bend Notre Dame Area

3 out of 5
Price was CA $966, price is now CA $879 per person
CA $879
per person
Aug 23 - Aug 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to South Bend (SBN)
9/10 Wonderful! (1,193 reviews)
The room and the hotel in general were clean and inviting. There are things that could have been better, like trim falling off the wall, and things could have been dusted. It is apparent that efforts are made to keep things clean, but nothing beyond that. Our stay was pleasant, and the staff was wonderful.

Reviewed on Jul 2, 2026

Baymont By Wyndham South Bend

Baymont By Wyndham South Bend

2.5 out of 5
Price was CA $829, price is now CA $762 per person
CA $762
per person
Aug 23 - Aug 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to South Bend (SBN)
8.4/10 Very good! (509 reviews)
Pool was closed. Breakfast was nice with hot food.

Reviewed on Jul 1, 2026

Holiday Inn Mishawaka by IHG

Holiday Inn Mishawaka by IHG

3 out of 5
Price was CA $945, price is now CA $924 per person
CA $924
per person
Aug 23 - Aug 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to South Bend (SBN)
8.6/10 Excellent! (1,008 reviews)
Good

Reviewed on Jun 30, 2026

Ready to book your vacation to Middlebury?

 

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Middlebury Hotel Deals

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 $152 per night from Jul 5 to Jul 6
CA $152
CA $171 total
Jul 5 - Jul 6
includes taxes & fees
9.6/10 Exceptional! (1,001 reviews)
"Amazing experience !!! The staff , rooms , beds and thoughtful decor made this a special experience for me and my wife . We will definitely be back again !"

Reviewed on Jun 30, 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 CA $184 per night from Jul 19 to Jul 20
CA $184
CA $206 total
Jul 19 - Jul 20
includes taxes & fees
8.2/10 Very good! (1,003 reviews)
"Breakfast was great location great"

Reviewed on Jul 2, 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 CA $220 per night from Jul 5 to Jul 6
CA $220
CA $266 total
Jul 5 - Jul 6
includes taxes & fees
10/10 Exceptional! (58 reviews)
"Exceptionally clean and very easy check in/out process."

Reviewed on Jul 2, 2026

Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
See all 593 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

Stay near popular Middlebury attractions

Stone Lake

Commune with nature and explore the great outdoors at Stone Lake during your travels in Middlebury. While in this family-friendly area, you can enjoy the restaurants.
See properties

Frequently asked questions

How much does a Middlebury vacation package cost?
Offering excellent value package deals from CA $740 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.

Explore a world of travel with Expedia

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