Middletown Vacations from $499
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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.
Holiday Inn Express Hartford South - Rocky Hill by IHG
Price was $664, price is now $499 per person
$499
per person
Dec 23 - Dec 30
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Hartford (BDL)
8.6/10 Excellent! (1,003 reviews)
We had a wonderful 4-night stay. The ENTIRE staff were happy and busy doing their job well. Management must be superb because the employees appear to enjoy their jobs…they act like one big family. I’ve never seen a hotel with this much cohesiveness. They take pride in all they do including constantly maintaining the property. Staff were always visible. We’ve stayed in hundreds of hotels and this one stands out as a true gem. Well done!
Reviewed on Oct 9, 2025
Hilton Garden Inn Hartford South/Glastonbury
Save 100% on your flight
Price was $839, price is now $598 per person
$598
per person
Dec 23 - Dec 30
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Hartford (BDL)
8.6/10 Excellent! (988 reviews)
Just what we needed staff was great and the bed were comfortable.
Reviewed on Sep 20, 2025
Howard Johnson by Wyndham Hartford South – Rocky Hill
Price was $647, price is now $526 per person
$526
per person
Dec 23 - Dec 30
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Hartford (BDL)
8.2/10 Very Good! (1,002 reviews)
Room was clean and recently updated, linens changed every day, staff was very courteous and extremely helpful
Reviewed on Oct 5, 2025
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.
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.
Kidcity Children's Museum
You can take time to visit Kidcity Children's Museum during your travels to Washington Street Historic District. Experience the festivals and entertainment venues in this family-friendly area.
Middletown Hotel Deals
Inn at Middletown
70 Main Street, Middletown, CT
Fully refundableReserve now, pay when you stay
$219 nightly
The price is $249 total per night from Oct 13 to Oct 14
$249 total
Oct 13 - Oct 14
Total with taxes and fees
8.8/10 Excellent! (509 reviews)
"The Inn is a neat property but feels a bit old and stuffy. Our room had a lot of small flies in the bathroom and the fan did not seem to work at all. It was really hard to connect with the hotel via phone - took numerous phone calls. The hotel does not seem staffed appropriately as the front desk ..."
Reviewed on Oct 8, 2025
The Capitol Hotel
440 Asylum St, Hartford, CT
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $118 total per night from Oct 12 to Oct 13
$118 total
Oct 12 - Oct 13
Total with taxes and fees
7.4/10 Good! (1,011 reviews)
"Friendly staff!"
Reviewed on Oct 7, 2025
Omni New Haven Hotel at Yale
155 Temple St, New Haven, CT
Fully refundableReserve now, pay when you stay
$167 nightly
The price is $192 total per night from Oct 26 to Oct 27
$192 total
Oct 26 - Oct 27
Total with taxes and fees
8.4/10 Very Good! (1,005 reviews)
"We have a lovely stay at the Omni New Haven. The room was clean and quiet with a super comfy bed and pillows. The staff were friendly and helpful. If you are visiting Yale, it's right on the campus. Very walkable!"
Reviewed on Oct 6, 2025
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.
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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- Main Street Historic District Hotels
- Cabin Rentals in Main Street Historic District
- 5 Star Hotels in Main Street Historic District
- Hotels near Kidcity Children's Museum
- Washington Street Historic District Hotels
- Apartments in Washington Street Historic District
- Hotels near Wesleyan University
- Hotels near Harbor Park
- Hotels near Van Vleck Observatory
- Portland Hotels
- Cabin Rentals in Portland
- Motels in Portland
- B&B in Portland
- Hotels near Brownstone Exploration & Discovery Park
- Hotels near Artfarm
- Hotels near Connecticut River State Wildlife Area
- Cromwell Hotels
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- Hotels near Wadsworth Mansion
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- Hotels near Wadsworth Falls State Park
- Hotels near Arrigoni Winery
- Rockfall Hotels
- Hotels near Smith Park
- Hotels near Dooley Pond Public Access
- Main Street Historic District Vacations
- Kidcity Children's Museum
- General Mansfield House
- Harbor Park
- Visit Main Street Historic District
- Van Vleck Observatory
- Brownstone Exploration & Discovery Park
- Visit Portland
- Connecticut River State Wildlife Area
- Cromwell Meadows Wildlife Management Area
- Wadsworth Mansion
- Cromwell Vacations
- Middletown Nature Gardens
- Visit Cromwell
- Arrigoni Winery
- Rockfall Vacations
- Ron McCutcheon Park
- Smith Park
- Dooley Pond Public Access
- Visit Rockfall
- River Highlands State Park
- Cromwell Commons Shopping Center
- Dart Island State Park
- Car rentals near Main Street Historic District
- Car rentals near Washington Street Historic District
- Car rentals near Wesleyan University
- Car rentals near Portland
- Firefly Rental Cars in Portland
- Car rentals near Cromwell
- Hertz Rental Cars in Cromwell
- Car rentals near Middletown Nature Gardens
- Car rentals near Rockfall
- Car rentals near Cromwell Commons Shopping Center
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.