Middletown Holidays

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Photo by Tiffany Zhou

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    Save up to £335 when you book a flight and hotel together*
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    Packages with flights are ATOL protected

Your Middletown Holiday

With all the details planned before you head off, our Middletown holiday packages mean you can focus more on having a good time. Whether you're staying in the neighbourhood of Main Street Historic District, which is good for history, or someplace else in town, this interesting city offers a wealth of discoveries. Wesleyan University, Brownstone Exploration & Discovery Park and TPC River Highlands are just a few of the sights you'll want to explore during your trip to Middletown. No matter your travel plans or budget, organising your ultimate tailored Middletown holiday is a breeze with Expedia.

Middletown Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Bradley Intl. Airport (BDL)
Population
46,800
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Brownstone Exploration & Discovery Park, Dinosaur State Park and Powder Ridge Mountain Park and Resort

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
8.8/10 Excellent! (486 reviews)
"Pool deck area was a little dirty."

Reviewed on 11 Jul 2025

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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 £71 per night from 17 Jul to 18 Jul
£71
17 Jul - 18 Jul
includes taxes & fees
7.4/10 Good! (1,029 reviews)
"The equipment in the fitness room was broken throughout the duration of our stay."

Reviewed on 10 Jul 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 £124 per night from 20 Jul to 21 Jul
£124
20 Jul - 21 Jul
includes taxes & fees
8.8/10 Excellent! (1,648 reviews)
"Very clean and spacious rooms"

Reviewed on 12 Jul 2025

New Haven Hotel
See all 1,176 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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Popular places to visit

Wadsworth Mansion

Learn about the local history of Middletown when you take a trip to Wadsworth Mansion. Experience the area's entertainment venues and festivals.

Wadsworth Mansion

Frequently asked questions

How much does a Middletown travel package cost?
From as low as . Yes, you read that correctly. Our Middletown travel packages are the easiest way to stretch your budget. Bundle your flights, hotels and rental car and discover this top destination.
If I'm not able to travel, can I cancel my Middletown travel package?
If your travel plans in Middletown have been upended, it's comforting to know that it's possible to cancel or amend your booking. If your booking was made within the last 24 hours, you may be eligible for a refund. If your booking is older than that, your airline, hotel or car rental company may impose a fee. To learn more, check our Customer Service Portal.
How do I get a cheap travel package to Middletown?
It's easy. Just bundle everything together. Flights, hotels and rental cars --- combine whatever you need into a Middletown travel package and save. Score even more bargains when you include extras such as tours or experiences to your booking. But that's not the only impressive part. You have the flexibility to put together your trip your way. We offer more than 550 partner airlines and 1,000,000 properties globally, so that everyone has an opportunity to travel and fulfil those holiday fantasies.
Does Expedia offer Book Now, Pay Later Middletown holidays?
Expedia has teamed up with online lender Klarna to make your next getaway easier on your budget. Paying in instalments means you can spread the costs of your next big holiday, leaving you with more cash to splash while you're away. Klarna has several payment plans to pick from, so you're sure to find something that fits into your budget. Take a look at these flexible payment options:

  • Pay monthly holidays: Realise your holiday dreams sooner with Klarna's easy monthly instalment plans. If making small repayments each month works for you, pick this option at checkout.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna allows you to pay for your trip in multiple transactions.
  • Low deposit holidays: When you want to grab an incredible deal but don't have the full amount yet, Klarna's low deposit holiday plan will help you lock it in.

Where should I stay in Middletown?
With so much to explore in Middletown, it'd be convenient for you to lock in a hotel near its attractions. Wesleyan University, Brownstone Exploration & Discovery Park and Wadsworth Mansion are some fascinating ones to add to your itinerary.
What are the top hotels in Middletown?
If it's your first time staying in Middletown, secure a room at Hilton Stamford Hotel & Executive Meeting Centre or Howard Johnson by Wyndham Mystic. Both have good amenities and are favourites among lots of travellers.
How far in advance should I book my Middletown holiday?
Reserving your tickets early with Expedia means one less thing to worry about. Most air carriers advertise tickets up to 12 months prior to take off. Generally, this is the cheapest time to book. If circumstances have left you booking late, discount tickets to Middletown sometimes emerge just weeks before departure.
What does an Expedia Middletown travel package include?
It comes down to what you want. If you're travelling solo, you might decide to combine flights and hotels. Taking the whole family to Middletown? A travel package including hotels, rental cars and flights might suit you better. Expedia gives you the freedom to build your own travel package.
What should I know before booking a Middletown travel package?
An Expedia travel package can be customized for your circumstances and is a simple way to make your budget go further. How much you include is up to you. Hotels, rental cars and flights --- come up with a combination that works with your plans.
Can I choose my airline with a Middletown Expedia travel package?
Yes --- that's one of the best things about an Expedia package. You're in control. We have access to more than 550 airline partners all over the world, so you have lots of choice when organising your Middletown trip.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.