Middletown Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Middletown

Inn at Middletown

Inn at Middletown

3.5 out of 5
70 Main Street Middletown CT
Fully refundableReserve now, pay when you stay
The price is 5.647.666 ₫ per night from 20 Jul to 21 Jul
5.647.666 ₫
7.019.935 ₫ total
20 Jul - 21 Jul
includes taxes & fees
9/10 Wonderful! (625 reviews)
"The staff is what puts this hotel the best. Mason at the front desk and Lisa in the restaurant. Would stay again if we are in the area."

Reviewed on 15 Jul 2026

Inn at Middletown
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 3.394.507 ₫ per night from 9 Aug to 10 Aug
3.394.507 ₫
3.903.683 ₫ total
9 Aug - 10 Aug
includes taxes & fees
9.2/10 Wonderful! (2,209 reviews)
"Very clean, spacious room! Included mini fridge, safe, ironing board, hair dryer, and robe (!). There was in-room coffee and also large pots of drip coffee in the lobby. I would stay here again if I am ever in New Haven."

Reviewed on 16 Jul 2026

New Haven Hotel
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Fully refundable
The price is 2.404.524 ₫ per night from 19 Jul to 20 Jul
2.404.524 ₫
2.765.281 ₫ total
19 Jul - 20 Jul
includes taxes & fees
8/10 Very good! (1,000 reviews)
"Still the same wonderful little place as the last time I stayed here!"

Reviewed on 11 Jul 2026

Pier Blue Inn Old Saybrook - Essex
See all 1,305 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.

Stay near popular Middletown attractions

A large white building with columns and a central staircase.

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.
See properties

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.

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