Middlebury Vacations from $474

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Your Middlebury Vacation

You'll find plenty to like about Middlebury, from its rich history to its cultural experiences. When you're ready to say hello to this fascinating city, our Middlebury vacation packages are calling your name. A trip to Middlebury is a terrific opportunity to sightsee. Be sure to visit popular attractions like Quassy Amusement Park, Palace Theatre and Brass Mill Center. No matter your travel plans or budget, organizing your ultimate tailored Middlebury vacation is a breeze with Expedia.

The Latest Middlebury vacation packages

Price found within the past 48 hours. Click for updated prices.
Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
Price was $539, price is now $474 per person
$474
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip flight included
Miami (MIA) to New Haven (HVN)
8.2/10 Very Good! (1,883 reviews)

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was $1,827, price is now $1,360 per person
$1,360
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip flight included
Miami (MIA) to New Haven (HVN)
No reviews

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Price was $649, price is now $546 per person
$546
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip flight included
Miami (MIA) to New Haven (HVN)
8.6/10 Excellent! (1,105 reviews)

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $671, price is now $592 per person
$592
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip flight included
Miami (MIA) to New Haven (HVN)
9.2/10 Wonderful! (1,002 reviews)

Hilton Garden Inn Milford

Hilton Garden Inn Milford

3 out of 5
Price was $650, price is now $585 per person
$585
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip flight included
Miami (MIA) to New Haven (HVN)
8.8/10 Excellent! (1,004 reviews)
Easy check in, good price,clean room,nice lobby with a bar on site if you would like a drink. Very friendly and attentive staff and a delicious breakfast for a reasonable price. Pool was great and gym is small but has everything you would need to get in a good workout to start your day .

Reviewed on Nov 2, 2026

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Stay near popular Middlebury attractions

Quassy Amusement Park

8.2/10 (21 reviews)
This century-old Connecticut park balances nostalgia with modern thrills, featuring the award-winning Wooden Warrior coaster and lakeside beach. Rent a waterpark cabana for a premium experience during hot summer days.
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Middlebury Hotel Deals

New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
$135 nightly
The price is $155 total per night from Nov 25 to Nov 26
$155 total
Nov 25 - Nov 26
Total with taxes and fees
New Haven Hotel
Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
490 Saw Mill Rd West Haven CT
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $126 total per night from Nov 22 to Nov 23
$126 total
Nov 22 - Nov 23
Total with taxes and fees
Best Western Executive Hotel Of New Haven - West Haven
Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
190 Old Gate Lane Milford CT
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $131 total per night from Nov 21 to Nov 22
$131 total
Nov 21 - Nov 22
Total with taxes and fees
Hyatt Place Milford / New Haven
See all 1,106 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.

Find the Best Middlebury Vacation Packages

Middlebury Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Tweed - New Haven Regional Airport (HVN)
Population
7,000
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Quassy Amusement Park, Palace Theatre and Mount Southington Ski Area

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Frequently asked questions

How much does a Middlebury vacation package cost?
You can grab a vacation package to this top destination from $474 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're likely to find lower prices and better availability in December, January and February. Take a look at our cheap Middlebury vacation packages and you could get some excellent off-season deals.
How many days is enough for Middlebury?
With a well-planned schedule, you can easily visit the most popular Middlebury sights in a handful of days. But if you want to venture off the beaten track or take day trips, consider booking your Middlebury vacation for longer.
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.
Does Expedia offer Book Now, Pay Later Middlebury vacation packages?
If you're anything like us, you love jet-setting around the world but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the overall cost of your Middlebury vacation across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure great vacation packages with payment plans as soon as you spot them.

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