Middlebury Vacations

Book a Hotel + Flight or Car together to unlock savings

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    Better together
    Save up to NT$5,067 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Find the Best Middlebury Vacation Packages

Middlebury Hotel Deals

New Haven Hotel
New Haven Hotel
3.5 out of 5
229 George Street, New Haven, CT
Fully refundableReserve now, pay when you stay
The price is NT$4,204 per night from Jul 2 to Jul 3
NT$4,204
NT$4,835 total
Jul 2 - Jul 3
includes taxes & fees
8.8/10 Excellent! (1,612 reviews)
"Great place and the staff is top notch! It is located in an area with lots of restaurants and bars nearby. Not far from the Yale campus and all of the stores to shop at. I’d definitely stay again."

Reviewed on 2025/6/25

New Haven Hotel
Clarion Inn
Clarion Inn
3 out of 5
201 Washington Avenue, North Haven, CT
Fully refundableReserve now, pay when you stay
The price is NT$2,960 per night from Jul 23 to Jul 24
NT$2,960
NT$3,405 total
Jul 23 - Jul 24
includes taxes & fees
7.4/10 Good! (1,008 reviews)
"A great stay for our family weekend event. Carpet in the rooms need to be steamed cleaned."

Reviewed on 2025/6/23

Clarion Inn
Courtyard by Marriott Waterbury Downtown
Courtyard by Marriott Waterbury Downtown
3 out of 5
63 Grand St, Waterbury, CT
Fully refundableReserve now, pay when you stay
The price is NT$2,605 per night from Jun 29 to Jun 30
NT$2,605
NT$2,996 total
Jun 29 - Jun 30
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
"Very comfortable room"

Reviewed on 2025/6/24

Courtyard by Marriott Waterbury Downtown
See all 957 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.

Frequently asked questions

How much does a Middlebury vacation package cost?
You can grab a vacation package to this top destination on Expedia. However, how much your vacation to Middlebury costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Middlebury?
You can usually find lower rates and better availability in January, February and March. Explore our cheap Middlebury vacation packages and you could land some great off-season deals.
How many days is enough for Middlebury?
The ideal duration of your Middlebury vacation depends on what you'd like to see and do. Generally, a few days to a week will give you plenty of time to check out all the leading sights and discover some hidden treasures along the way.
Is it worth booking a vacation package to Middlebury?
From top attractions such as Middlebury Center Historic District and Quassy Amusement Park to its terrific golfing, a Middlebury vacation delivers big on experiences. With so much to do and see, it's time to find out for yourself why Middlebury is such a good vacation destination.
How to find the best Middlebury package deals?
Landing a cheap Middlebury package deal is a breeze with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, add some filters and see what's available. You can tweak your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Middlebury package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Middlebury vacation as a package?
You can enjoy significant savings on your next Middlebury getaway by booking a customized vacation package. Click on the "Package" heading, then select your destination and travel dates to view the best flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Middlebury?
If you have your Middlebury vacation dates finalized, book as early as you can to score some terrific deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Middlebury?

  1. Choose when to get away: Check your calendar and get packing. Your preferred season and the type of activities on offer will also help you decide when to vacation in Middlebury.
  2. Plan your budget wisely: On top of the price of your accommodations, you should factor in other expenses too. These include food, transportation and flights. Also, set aside some extra funds for unexpected expenses that could arise during your trip to Middlebury.
  3. Work out your trip length: Think about how long you'd like to spend exploring Middlebury. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Bundle your accommodations and airfare: Once you've settled on your trip dates and duration, lock in the ideal 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.