Middlebury Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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.
The Inn at Saint Mary's
CA $1,338
per person
Oct 2 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to South Bend (SBN)
9.4/10 Exceptional! (1,290 reviews)
The room was beautiful and the towels and toilet paper had that extra special touch. The hotel was under construction and I did go to the Bistro next door to get something to eat.
I would stay there again, specially if I had a car to get around.
The staff was extremely nice and I got a shuttle ride to and from the Airport.
Reviewed on Aug 19, 2026
Ready to book your vacation to Middlebury?
Middlebury Hotel Deals
Essenhaus Inn & Conference Center
240 Hwy 20 Middlebury IN
Fully refundableReserve now, pay when you stay
CA $149
CA $166 total
Sep 13 - Sep 14
includes taxes & fees
9.6/10 Exceptional! (1,014 reviews)
"all was nice"
Reviewed on Aug 19, 2026
Hampton Inn & Suites Middlebury
105 Crystal Heights Blvd Middlebury IN
CA $164
CA $183 total
Sep 3 - Sep 4
includes taxes & fees
8.2/10 Very good! (1,004 reviews)
"Front desk staff and housekeeping staff very friendly. The breakfast had a nice variety of food options. Enjoyed the hot tub. The room and bed was comfortable. We would stay here again"
Reviewed on Aug 17, 2026
Charming 2-bedroom cottage with WiFi, AC in peaceful Middlebury
Middlebury IN
CA $215
CA $262 total
Aug 23 - Aug 24
includes taxes & fees
10/10 Exceptional! (66 reviews)
"Charming little home. Very clean and comfortable. Central to all the things we wanted to do. We would definitely stay here again."
Reviewed on Aug 17, 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
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.
Deutsch Kase Haus
9.2/10 (39 reviews)
Enjoy an outing to Deutsch Kase Haus during your stay in Middlebury. While in this relaxing area, find time to visit its shops.
Meadow Valley Golf Club
Enjoy a round of golf in Middlebury at Meadow Valley Golf Club. While in this family-friendly area, you can enjoy the restaurants.
Middlebury Public Library
After visiting Middlebury Public Library, make a plan to see the other sights and activities in Middlebury. While in this family-friendly area, you can enjoy the restaurants.
Trout Lake
Commune with nature and explore the great outdoors at Trout Lake during your travels in Middlebury. While in this family-friendly area, you can enjoy the restaurants.
Corson Riverwoods County Park
After visiting Corson Riverwoods County Park, make a plan to see the other sights and activities in Middlebury. While in this family-friendly area, you can enjoy the restaurants.
Hunter Lake
Commune with nature and explore the great outdoors at Hunter Lake during your travels in Middlebury. While in this family-friendly area, you can enjoy the restaurants.
Middlebury Community Historical
You can spend an afternoon studying the exhibits at Middlebury Community Historical in Middlebury. While in this family-friendly area, you can enjoy the restaurants.
Frequently asked questions
How much does a Middlebury vacation package cost?
Offering excellent value package deals from CA $1,171 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?
- 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.
- 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.
- 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.
- 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.
