Middlebury Vacations from $506

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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.
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
Price was $654, price is now $506 per person
$506
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)
8/10 Very Good! (1,001 reviews)
Still the same wonderful little place as the last time I stayed here!

Reviewed on Jul 11, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was $1,432, price is now $1,099 per person
$1,099
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)
No reviews

Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Price was $1,261, price is now $970 per person
$970
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)
2/10 (1 review)
The parking situation is very unclear. There is a small sign far from the lot that warns of towing but nothing in the area where you park. No significant warnings in communications with host.

Reviewed on May 25, 2026

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Price was $1,034, price is now $798 per person
$798
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)
8.6/10 Excellent! (1,040 reviews)
Room was not ready after 4 pm. But hotel is nicely maintained

Reviewed on Jul 12, 2026

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $905, price is now $713 per person
$713
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)
9.2/10 Wonderful! (1,005 reviews)
N/A

Reviewed on Jul 12, 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.
See properties

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
$144 nightly
The price is $165 total per night from Jul 26 to Jul 27
$165 total
Jul 26 - Jul 27
Total with taxes and fees
9.2/10 Wonderful! (2,226 reviews)
"The balcony view was good...the breeze and the flying seagulls were a great way to start my morning. Breakfast was available for purchase, but I did not buy anything."

Reviewed on Jul 14, 2026

New Haven Hotel
Trumbull Marriott Shelton

Trumbull Marriott Shelton

3.5 out of 5
180 Hawley Ln Trumbull CT
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $175 total per night from Jul 26 to Jul 27
$175 total
Jul 26 - Jul 27
Total with taxes and fees
7.8/10 Good! (1,016 reviews)
"Good Staff was very attentive. Checking experience was great. Checkout experience was great. Not so great It’s an older hotel. It was clean but my room did smell like cigarettes. It bothered me but not my wife so other people might not notice. There were little things like rust on the door frame ..."

Reviewed on Jul 13, 2026

Trumbull Marriott Shelton
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
$114 nightly
The price is $131 total per night from Jul 19 to Jul 20
$131 total
Jul 19 - Jul 20
Total with taxes and fees
8/10 Very Good! (1,721 reviews)
"Everything was great !! except the internet as my stay included me working from the hotel most the day."

Reviewed on Jul 13, 2026

Best Western Executive Hotel Of New Haven - West Haven
See all 1,094 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 $506 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.