Middlebury Vacations from $476

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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.
Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $582, price is now $476 per person
$476
per person
Sep 4 - Sep 7
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
9.2/10 Wonderful! (1,008 reviews)
I loved the location and the character of this property! Every person I encountered on the staff went above and beyond. I'm from the south so I appreciate the friendliness of these folks. I was greeted every time I came and went, which was a lot, and they truly seemed to care about my stay. The only negative I have is that they don't have a full-service restaurant on site. I stayed at the property for almost a week. It would have been nice to be able to eat in a night or two. Also, guests need to know that there is no parking. I was worried about that at first, but it turned out to be just fine. The Yale garage at Chapel and York was convenient, reasonably priced and safe, but I was nervous when I first realized that parking at this hotel is not an option. Overall, I enjoyed my stay and will come back if I am in the area again.

Reviewed on Jul 23, 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 $1,590, price is now $1,187 per person
$1,187
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Tampa (TPA) 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

Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
The Hill
Save 100% on your flight
Price was $785, price is now $607 per person
$607
per person
Sep 4 - Sep 7
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
9.2/10 Wonderful! (32 reviews)
Everything about the property & staff was AMAZING! Zero complaints, would 100% stay there again if in the area. Thank you!

Reviewed on Jul 24, 2026

Luxury Furnished Apartments by Hyatus Downtown at Yale

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 out of 5
The Hill
Save 100% on your flight
Price was $897, price is now $709 per person
$709
per person
Sep 4 - Sep 7
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
9.6/10 Exceptional! (85 reviews)
I had an amazing stay at the Hyatus. The property was exceptionally clean and well maintained, which made me feel comfortable from the moment I arrived. The location was perfect—convenient to everything I needed while still being quiet and peaceful, making it easy to relax after a busy week. Overall, it was a wonderful experience, and I would absolutely stay here again. Highly recommend!

Reviewed on Jul 6, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was $1,379, price is now $1,122 per person
$1,122
per person
Aug 28 - Aug 31
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
No reviews

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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

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St Southington CT
Fully refundable
$91 nightly
The price is $104 total per night from Aug 2 to Aug 3
$104 total
Aug 2 - Aug 3
Total with taxes and fees
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
$152 nightly
The price is $175 total per night from Aug 2 to Aug 3
$175 total
Aug 2 - Aug 3
Total with taxes and fees
7.8/10 Good! (1,006 reviews)
"Comfortable bed, helpful staff, always a good stay when I come for a convention each year."

Reviewed on Jul 25, 2026

Trumbull Marriott Shelton
New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
$133 nightly
The price is $153 total per night from Aug 2 to Aug 3
$153 total
Aug 2 - Aug 3
Total with taxes and fees
9.2/10 Wonderful! (2,252 reviews)
"The staff was very friendly and helpful with recommendations for where to eat in the nearby area."

Reviewed on Jul 26, 2026

New Haven Hotel
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 $476 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.