Middletown Holidays

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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 S$356 per night from 31 Mar to 1 Apr
S$356
includes taxes & fees
31 Mar - 1 Apr
9/10 Wonderful! (452 reviews)
Middletown Gem
"The Inn is quaint, cozy and inviting. The front desk staff were extremely friendly and helpful. Especially enjoyed dining in the Tavern...all the wait staff awesome! Highly recommend staying!!!"

Reviewed on 3 Mar,2025

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 S$182 per night from 6 Apr to 7 Apr
S$182
includes taxes & fees
6 Apr - 7 Apr
8.8/10 Excellent! (1,475 reviews)
"Close to Yale theater. Reasonably priced."

Reviewed on 27 Mar,2025

New Haven Hotel
Omni New Haven Hotel at Yale
Omni New Haven Hotel at Yale
4 out of 5
155 Temple St, New Haven, CT
Fully refundableReserve now, pay when you stay
The price is S$221 per night from 28 Apr to 29 Apr
S$221
includes taxes & fees
28 Apr - 29 Apr
8.2/10 Very Good! (1,002 reviews)
"The front desk associate, Kevin, was awesome!"

Reviewed on 25 Mar,2025

Omni New Haven Hotel at Yale
See all 1,157 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

Ron McCutcheon Park

Explore the great outdoors at Ron McCutcheon Park, a lovely green space in Middletown. Experience the entertainment venues and festivals in this family-friendly area.

Ron McCutcheon Park

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.