Middletown Vacations from $568

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Your Middletown Vacation

With all the details planned before you head off, our Middletown vacation packages mean you can focus more on having a good time. Whether you're staying in the neighborhood of Main Street Historic District, which is good for history, or someplace else in town, this interesting city offers a wealth of discoveries. Wesleyan University, Brownstone Exploration & Discovery Park and TPC River Highlands are just a few of the sights you'll want to explore during your trip to Middletown. No matter your travel plans or budget, organizing your ultimate tailored Middletown vacation is a breeze with Expedia.

The Latest Middletown vacation packages

Price found within the past 48 hours. Click for updated prices.
Best Western Manchester

Best Western Manchester

2.5 out of 5
per person
Aug 10 - Aug 17
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
8.6/10 Excellent! (132 reviews)
It was super late when we checked in but everything was clean and nice room. Very comfortable.

Reviewed on Jul 2, 2025

Hilton Garden Inn Hartford South/Glastonbury

Hilton Garden Inn Hartford South/Glastonbury

3 out of 5
Save 100% on your flight
per person
Aug 10 - Aug 17
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
8.6/10 Excellent! (948 reviews)
The property is kind of old but it was clean and well maintained, the area was quiet with easy parking. The staff was friendly and professional.

Reviewed on Jun 30, 2025

Holiday Inn Express Vernon - Manchester by IHG

Holiday Inn Express Vernon - Manchester by IHG

2.5 out of 5
per person
Aug 10 - Aug 17
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
8.4/10 Very Good! (997 reviews)
The hotel could use updating, the rooms were neat and clean but they showed their age a bit. The handicapped shower did not have a transfer bench or seat.

Reviewed on Jul 3, 2025

DoubleTree by Hilton Hartford Downtown

DoubleTree by Hilton Hartford Downtown

4 out of 5
Downtown Hartford
Save 100% on your flight
per person
Aug 10 - Aug 17
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
7.6/10 Good! (1,001 reviews)
Went for a festival and it was perfect walking distance to the park and the cleaning staff was amazing

Reviewed on Jul 4, 2025

DoubleTree by Hilton Hartford - Bradley Airport

DoubleTree by Hilton Hartford - Bradley Airport

4 out of 5
per person
Aug 10 - Aug 17
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Hartford (BDL)
8/10 Very Good! (1,004 reviews)
I wish the room was more updated and cleaner. There was hair all in my bathroom. It was a good stay though

Reviewed on Jun 30, 2025

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Discover the most popular places to visit in Middletown

Wesleyan University

4/5(89 reviews)

Enjoy the collegiate vibe when you visit Wesleyan University, during your travels in Middletown. Experience the area's festivals or attend a sporting event.

Wesleyan University

Wadsworth Mansion

Learn about the local history of Middletown when you take a trip to Wadsworth Mansion. Experience the area's entertainment venues and festivals.

Wadsworth Mansion

Harbor Park

4/5(5 reviews)

Harbor Park is just one of the places to see in Middletown, so why not enjoy the other things to explore during your travels? Experience the area's festivals and entertainment venues.

Harbor Park

Middletown Hotel Deals

The Capitol Hotel
The Capitol Hotel
3 out of 5
440 Asylum St, Hartford, CT
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $118 total per night from Jul 13 to Jul 14
$118 total
Jul 13 - Jul 14
Total includes taxes and fees
7.4/10 Good! (1,001 reviews)
"For me the hotel was fine, the staff friendly, the room clean, the price reasonable but the big advantage was how close it was to the Mark Twain home and museum which I enjoy visiting."

Reviewed on Jul 3, 2025

The Capitol Hotel
New Haven Hotel
New Haven Hotel
3.5 out of 5
229 George Street, New Haven, CT
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $155 total per night from Jul 21 to Jul 22
$155 total
Jul 21 - Jul 22
Total includes taxes and fees
8.8/10 Excellent! (1,627 reviews)
"The property was very nice with great customer service.We stayed on a Friday night and we could hear the music from the night club behind the hotel late into the night. Other than that I have no complaints about the property."

Reviewed on Jul 3, 2025

New Haven Hotel
Clarion Inn
Clarion Inn
3 out of 5
201 Washington Avenue, North Haven, CT
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $116 total per night from Aug 3 to Aug 4
$116 total
Aug 3 - Aug 4
Total includes taxes and fees
7.4/10 Good! (1,013 reviews)
"It had a good vibe walking in, the only thing I disliked was the Queen size bed was definitely a full size bed, but was marked as a queen size bed."

Reviewed on Jul 1, 2025

Clarion Inn
See all 1,171 properties in Middletown
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 Middletown Vacation Packages

Middletown Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Bradley Intl. Airport (BDL)
Population
46,800
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Brownstone Exploration & Discovery Park, Goodspeed Opera House and Dinosaur State Park

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Frequently asked questions

How much does a Middletown vacation package cost?
You'll find cheap prices from $568 on Expedia for your Middletown getaway. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your vacation to Middletown costs.
What are the cheapest months to go to Middletown?
You're likely to find reduced prices and greater availability in November, December and January. Check out our cheap Middletown vacation packages and you could score some great off-season discounts.
How many days is enough for Middletown?
We recommend booking a Middletown vacation for at least 2 days. This will give you plenty of time to tick off popular sights such as Van Vleck Observatory and Wesleyan University, as well as explore neighborhoods like Main Street Historic District and Washington Street Historic District. You could even slot in a day trip beyond Middletown.
Is it worth booking a vacation package to Middletown?
Popular for its family-friendly attractions, festivals and history, a Middletown vacation offers something for everyone. Be sure to visit main sights like Artfarm and Kidcity Children's Museum, and consider renting a car for day trips to discover even more.
How to find the best Middletown package deals?
Begin your search for a Middletown package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select some filters, like "Property type" and "Popular locations," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Middletown package deal right away, simply switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Middletown escape underway.
Is it cheaper to book a Middletown vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll typically land a better deal than booking each component individually. And you'll still get the freedom to create a customized Middletown vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Middletown?
Enjoy fantastic discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for an impromptu Middletown escape.
Does Expedia offer Book Now, Pay Later Middletown vacation packages?
Your Middletown getaway should be a relaxing escape from your busy life, not a source of money worries. So to give you a little more flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.