Middlebury Vacations from $424

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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 $577, price is now $424 per person
$424
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Nashville (BNA) to New Haven (HVN)
8/10 Very Good! (1,000 reviews)
Convenient, very outdated

Reviewed on Jun 22, 2026

Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Save 100% on your flight
Price was $1,378, price is now $988 per person
$988
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to New Haven (HVN)
2/10 (1 review)
New Haven Hotel

New Haven Hotel

3.5 out of 5
Downtown New Haven
Price was $577, price is now $435 per person
$435
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Nashville (BNA) to New Haven (HVN)
9.2/10 Wonderful! (2,194 reviews)
Excellent staff & great location - close to many different restaurants & the hospital. Also the hotel has a parking garage across the street which is wonderful

Reviewed on Jun 28, 2026

Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
The Hill
Save 100% on your flight
Price was $982, price is now $767 per person
$767
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Nashville (BNA) to New Haven (HVN)
9.2/10 Wonderful! (31 reviews)
Great stay with many amenities to enjoy within the building!

Reviewed on Apr 3, 2026

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $579, price is now $462 per person
$462
per person
Aug 7 - Aug 10
found 1 day ago
Roundtrip flight included
Nashville (BNA) to New Haven (HVN)
9.2/10 Wonderful! (995 reviews)
Beautiful, old building. Every thing was great from the room to the staff to breakfast. Cofee was awesome.

Reviewed on Jun 26, 2026

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Stay near popular Middlebury attractions

Quassy Amusement Park

8.2/5 (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
$106 nightly
The price is $121 total per night from Jul 5 to Jul 6
$121 total
Jul 5 - Jul 6
Total with taxes and fees
9.2/10 Wonderful! (2,208 reviews)
"Management was very rude but the staff were great and helpful."

Reviewed on Jun 29, 2026

New Haven Hotel
Hilton Garden Inn Milford

Hilton Garden Inn Milford

3 out of 5
291 Old Gate Lane Milford CT
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $128 total per night from Jul 5 to Jul 6
$128 total
Jul 5 - Jul 6
Total with taxes and fees
8.6/10 Excellent! (1,012 reviews)
"Was good I really didn’t have no complaints at all"

Reviewed on Jun 29, 2026

Hilton Garden Inn Milford
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
$103 nightly
The price is $119 total per night from Jul 1 to Jul 2
$119 total
Jul 1 - Jul 2
Total with taxes and fees
8/10 Very Good! (1,688 reviews)
"Great, safe stay! I’ve been several times when when my husband had Yale hospital stays."

Reviewed on Jun 29, 2026

Best Western Executive Hotel Of New Haven - West Haven
See all 1,096 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 $424 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.