Middletown Holidays
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Top hotels in Middletown
Inn at Middletown
70 Main Street Middletown CT
Fully refundableReserve now, pay when you stay
Rp3.421.906
Rp4.293.132 total
10 Aug - 11 Aug
includes taxes & fees
9/10 Wonderful! (635 reviews)
"Everyone there was so nice and helpful. The restaurant was fantastic. So glad we picked this place to stay. Highly recommended"
Reviewed on 8 Aug 2026
Motel 6 New Haven - Branford, CT
320 E Main St Branford CT
Fully refundable
Rp1.131.269
Rp1.318.830 total
3 Sept - 4 Sept
includes taxes & fees
7.2/10 Good! (1,019 reviews)
"Everything was great"
Reviewed on 8 Aug 2026
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Fully refundable
Rp1.757.664
Rp2.021.287 total
10 Aug - 11 Aug
includes taxes & fees
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.
Stay near popular Middletown attractions
Wadsworth Mansion
This Beaux-Arts masterpiece invites you into the grandeur of early 20th century American aristocracy. Wander through elegant interiors on Wednesday tours, then explore picturesque trails and gardens.
Harbor Park
8.0/10 (5 reviews)
Harbour Park offers tranquil riverside paths along the Connecticut River with perfect sunset views. Enjoy a picnic while watching boats pass by, or time your visit for the annual rowing races and Fourth of July fireworks.
Wesleyan University
8.6/10 (189 reviews)
Wesleyan University's historic 316-acre campus blends 19th-century architecture with cutting-edge facilities. Experience the vibrant intellectual community that has defined this liberal arts institution since 1831.
General Mansfield House
This stately Federal-style mansion showcases Middletown's Civil War heritage through period rooms and rare artefacts. Explore historical exhibits, then stroll gardens featuring a magnificent 150-year-old ginkgo tree.
Dooley Pond Public Access
Dooley Pond offers a serene freshwater fishing haven where anglers pursue largemouth bass and yellow perch. Launch your small boat from this peaceful access point and enjoy Connecticut's natural tranquility.
Middletown Nature Gardens
Wander through 18 acres of diverse Connecticut ecosystems, from woodlands to a rare red maple swamp. The 200-year-old "Bee Tree" sugar maple stands as a living monument to the garden's natural heritage.
Ron McCutcheon Park
This lakeside sanctuary honours Ron McCutcheon, who taught generations of local children to swim. Enjoy the sandy beach, picnic under pavilions, or explore walking trails through the 25-acre wildlife preserve.
Kidcity Children's Museum
10.0/10 (1 review)
This artist-crafted museum features three floors of imaginative play spaces designed for children ages 1-7. Explore medieval villages, fishing ships, and space-age adventures in detailed settings that spark creativity.
Frequently asked questions
How much does a Middletown holiday package cost?
You'll find cheap prices 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 holiday to Middletown costs.
What are the cheapest months to go to Middletown?
December, January and February are the best times to look for cheap Middletown holiday packages. Opting to travel in less busy months means you'll typically find better prices on hotels and flights.
How many days is enough for Middletown?
Middletown holidays can be short or long, but to really sink your teeth into this destination, we'd suggest 2 days is about right. This will mean you can fit in major attractions like Van Vleck Observatory and General Mansfield House and track down some hidden gems. Don't skip cool areas such as Main Street Historic District and Washington Street Historic District either. If you're clever with your time, you can even schedule a day trip outside of Middletown too.
Is it worth booking a holiday package to Middletown?
Well known for its family-friendly attractions, festivals and history, a Middletown holiday offers something for everyone. Be sure to check out major sights like Artfarm and General Mansfield House, and consider renting a car for day trips to experience 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 holiday as a package?
Expedia holiday 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 customised Middletown holiday by choosing your preferred type of stay, airline and car class.
When to book a holiday 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.
How to plan a trip to Middletown?
- Choose when to go: Check your schedule and get packing. Your favourite season and the activities available will also help you decide when to escape to Middletown.
- Calculate your budget: Ensure you have enough money to pay for everything from transportation and dining out to activities and airfares. Your hotel will likely be the biggest expense during your trip to Middletown.
- Decide how long to go for: Now that you're up to speed on Middletown, you can figure out the perfect length of your break. Pull together a draft plan and give yourself enough time to cover everything you want to see.
- Combine your airfare and accommodation: Once you've nailed down your trip dates and duration, lock in the ideal Middletown holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
