Middletown Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Simmie Reagor

Top hotels in Middletown

The Capitol Hotel
The Capitol Hotel
3 out of 5
440 Asylum St, Hartford, CT
Fully refundableReserve now, pay when you stay
The price is 2.677.347 ₫ per night from 2 Jul to 3 Jul
2.677.347 ₫
3.078.949 ₫ total
2 Jul - 3 Jul
includes taxes & fees
7.4/10 Good! (1,002 reviews)
"It's not luxurious BUT it is upgraded with modern conveniences and is CLEAN. I had a good night's rest on a comfortable bed and a nice hot shower. Parking is a little scary to navigate at first underground, but it was secure and I appreciate that because I returned back to my room after 2a.m."

Reviewed on 26 Jun 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
The price is 3.859.451 ₫ per night from 6 Jul to 7 Jul
3.859.451 ₫
4.438.368 ₫ total
6 Jul - 7 Jul
includes taxes & fees
8.8/10 Excellent! (1,603 reviews)
"Great place and the staff is top notch! It is located in an area with lots of restaurants and bars nearby. Not far from the Yale campus and all of the stores to shop at. I’d definitely stay again."

Reviewed on 25 Jun 2025

New Haven Hotel
Hampton Inn & Suites Hartford/East Hartford
Hampton Inn & Suites Hartford/East Hartford
2.5 out of 5
351 Pitkin Steet, East Hartford, CT
The price is 2.883.498 ₫ per night from 20 Jul to 21 Jul
2.883.498 ₫
3.316.023 ₫ total
20 Jul - 21 Jul
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
"Clean property and as others have noted, very friendly staff ! Breakfast was nice too. Will happily stay here again."

Reviewed on 28 Jun 2025

Hampton Inn & Suites Hartford/East Hartford
See all 1,167 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.

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?

  1. 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.
  2. 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.
  3. 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.
  4. Combine your airfare and accommodation: Once you've nailed down your trip dates and duration, lock in the ideal Middletown holiday package for you.

Popular places to visit

Harbor Park

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

Dooley Pond Public Access

Explore the great outdoors at Dooley Pond Public Access, a lovely green space in Middletown. Experience the entertainment venues and festivals in this family-friendly area.

Dooley Pond Public Access

Smith Park

Smith 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 festivals and entertainment venues in this family-friendly area.

Smith Park