Middlebury Vacations from $206

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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.
Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

3 out of 5
Price was $280, price is now $206 per person
$206
per person
Dec 6 - Dec 9
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)
8.2/10 Very Good! (1,009 reviews)
Clean, right off the highway. Pleasant and helpful staff.

Reviewed on Oct 22, 2025

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Save 100% on your flight
Price was $387, price is now $263 per person
$263
per person
Dec 6 - Dec 9
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)
9.2/10 Wonderful! (889 reviews)
The bar downstairs is so fun, and their pizza night provided us with the best pizza in New Haven (better than the famous spots we all know). The bartenders made our trip, and showed us the warmth of the people of New Haven. Do not skip the bar! Even if you do not drink, the games are great and the food is even better.

Reviewed on Oct 17, 2025

Madison Beach Hotel

Madison Beach Hotel

4 out of 5
Madison Center
Save 100% on your flight
Price was $738, price is now $518 per person
$518
per person
Dec 6 - Dec 9
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)
9.4/10 Exceptional! (323 reviews)
Beautiful beach property that gives you such a feeling of luxury all around you. Staff has been great, very clean hallways and entire property. Balcony is beautiful!

Reviewed on Oct 14, 2025

New Haven Hotel

New Haven Hotel

3.5 out of 5
Downtown New Haven
Save 100% on your flight
Price was $336, price is now $250 per person
$250
per person
Dec 6 - Dec 9
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)
9/10 Wonderful! (1,842 reviews)
Stephanie at the desk was so helpful and went above and beyond to enhance our stay. We appreciated the proximity to Yale within a 15-minute walk. So grateful for the laundry room! It was clean, secure, and directions easy to follow. This is our 4th stop on our Ivy League tour and the best accommodations so far.

Reviewed on Oct 21, 2025

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
Old Saybrook Center
Save 100% on your flight
Price was $979, price is now $744 per person
$744
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
9.4/10 Exceptional! (1,011 reviews)
Every aspect of this hotel was spotless

Reviewed on Oct 21, 2025

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Discover the most popular places to visit in Middlebury

Quassy Amusement Park

4.5/5(13 reviews)

Bring the kiddos to Quassy Amusement Park and have a fun-filled day at this theme park in Middlebury. Attend a sporting event in this family-friendly area.

Quassy Amusement Park

Middlebury Hotel Deals

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St, Southington, CT
Fully refundable
$98 nightly
The price is $113 total per night from Nov 16 to Nov 17
$113 total
Nov 16 - Nov 17
Total with taxes and fees
8.6/10 Excellent! (1,139 reviews)
"The room was clean and staff was friendly. We enjoyed the queen beds."

Reviewed on Oct 19, 2025

Holiday Inn Express Southington by IHG
Trumbull Marriott Shelton

Trumbull Marriott Shelton

3.5 out of 5
180 Hawley Ln, Trumbull, CT
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $160 total per night from Nov 2 to Nov 3
$160 total
Nov 2 - Nov 3
Total with taxes and fees
8/10 Very Good! (1,000 reviews)
"Nice facility overall. A few minor issues in the room that were quickly corrected."

Reviewed on Oct 16, 2025

Trumbull Marriott Shelton
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
155 Temple St, New Haven, CT
Fully refundableReserve now, pay when you stay
$167 nightly
The price is $192 total per night from Nov 15 to Nov 16
$192 total
Nov 15 - Nov 16
Total with taxes and fees
8.4/10 Very Good! (1,022 reviews)
"Perfect overall"

Reviewed on Oct 18, 2025

Omni New Haven Hotel at Yale
See all 945 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 $206 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.