Middletown Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Tiffany Zhou
    deals illustration
    Better together
    Save up to ￥45,448 when you book a flight and hotel together*
    stays illustration
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration
    Rest easy
    Plan, book, and manage your trip all in one place

Find the Best Middletown Vacation Packages

Middletown Hotel Deals

Inn at Middletown
Inn at Middletown
3.5 out of 5
70 Main Street, Middletown, CT
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (474 reviews)
"Helpful staff, cute hotel. Restaurant was closed in the AM for staffing or other probs… so had to find other breakfast but there are options walking distance."

Reviewed on May 29, 2025

Get rates
Inn at 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 ￥14,782 per night from Jul 1 to Jul 2
￥14,782
￥16,999 total
Jul 1 - Jul 2
includes taxes & fees
7.4/10 Good! (1,000 reviews)
"near downtown, you can walk to down town and most corporate locations"

Reviewed on Jun 12, 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 ￥20,083 per night from Jun 22 to Jun 23
￥20,083
￥23,095 total
Jun 22 - Jun 23
includes taxes & fees
8.8/10 Excellent! (1,592 reviews)
Great stay in New Haven
"Spacious, comfortable room, great beds and shower. Friendly staff. Parking."

Reviewed on Jun 13, 2025

New Haven Hotel
See all 1,165 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 vacation 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 vacation 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 vacation 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 vacations 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 vacation package to Middletown?
Well known for its family-friendly attractions, festivals and history, a Middletown vacation 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 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.
How to plan a trip to Middletown?

  1. Choose when to go: Check your schedule and get packing. Your favorite 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 accommodations: Once you’ve nailed down your trip dates and duration, lock in the ideal Middletown vacation package for you.

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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.