Middletown Vacations from $296

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Your Middletown Vacation

With all the details planned before you head off, our Middletown vacation packages mean you can focus more on having a good time. Whether you're staying in the neighborhood 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, organizing your ultimate tailored Middletown vacation is a breeze with Expedia.

The Latest Middletown vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Vernon - Manchester by IHG
Inn at Middletown
The Goodwin Hotel
Delamar West Hartford
Candlewood Suites Windsor Locks Bradley Arpt by IHG
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Discover the most popular places to visit in Middletown

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
$161 nightly
The price is $182 total per night from Dec 2 to Dec 3
$182 total
Dec 2 - Dec 3
Total with taxes and fees
8.8/10 Excellent! (532 reviews)
Parking is hard to accommodate guests.

Reviewed on Nov 19, 2025

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
$89 nightly
The price is $102 total per night from Nov 26 to Nov 27
$102 total
Nov 26 - Nov 27
Total with taxes and fees
7.4/10 Good! (1,086 reviews)
Clean rooms, convenient location, friendly staff and great price

Reviewed on Nov 22, 2025

The Capitol Hotel
Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
320 E Main St Branford CT
Fully refundable
$74 nightly
The price is $85 total per night from Nov 30 to Dec 1
$85 total
Nov 30 - Dec 1
Total with taxes and fees
7/10 Good! (1,008 reviews)
Stay here because it’s clean and the price is right for the money you can’t beat it plus you have excellent food at Capones restaurant 100 feet away for your convenience

Reviewed on Nov 25, 2025

Motel 6 New Haven - Branford, CT
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.

Find the Best Middletown Vacation Packages

Things to do in and around Middletown

Middletown, Connecticut, is perfect for a culture-themed, outdoor, or romantic vacation. Visitors can enjoy a variety of activities such as exploring educational attractions, playing a round of golf at local courses, and attending vibrant music concerts. Whether you're looking for a golf getaway, a romantic retreat, or day tours, Middletown offers a wonderful mix of experiences to make your vacation memorable.

Shopping

Middletown offers great shopping options like Cromwell Commons Shopping Center, just 4 miles away, featuring entertainment and family-friendly vibes. Brickyard Shopping Center, 7 miles away, has a mix of business and city energy. If you're up for a drive, visit Sundial Herb Garden, located 10 miles from Middletown.

Recreation

At TPC River Highlands, enjoy a round of golf surrounded by beautiful landscapes, perfect for relaxation and outdoor fun. The Van Vleck Observatory offers family-friendly stargazing experiences, while Artfarm provides a charming venue for theater, blending culture and entertainment for a delightful evening out.

Adventure

At Brownstone Exploration & Discovery Park, located 0.9 miles from Middletown, you can enjoy thrilling water sports and rock climbing in a vibrant family atmosphere. Powder Ridge Mountain Park and Resort, 6 miles away, offers exhilarating skiing experiences. For a peaceful outdoor escape, visit Cromwell Meadows Wildlife Management Area, 2 miles from Middletown.

Nightlife

Middletown's nightlife offers a vibrant mix of bars and live music. Visit the Buttonwood Tree for eclectic performances and enjoy cocktails at the Midnight Cafe. For a laid-back vibe, head to the Italian Club for a friendly atmosphere and great food, making it a perfect night out.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in Middletown

Middletown, Connecticut, offers a delightful blend of culture and outdoor activities, perfect for romantic getaways or family experiences. Explore local attractions like state parks, urban parks, and historic colleges to immerse yourself in the area's rich heritage. Don't miss the chance to relax at the beach in Middletown, adding a touch of seaside charm to your vacation. Enjoy the vibrant mix of nature and culture that this charming town has to offer.

  • Wesleyan University: Experience the rich history and vibrant culture of Wesleyan University, a historic institution nestled in the heart of Middletown. The campus features stunning architecture, art galleries, and a lively atmosphere that attracts students and visitors alike.
  • Wadsworth Mansion: Step into elegance at Wadsworth Mansion, a beautiful event venue that exudes sophistication. With its grand architecture and lush gardens, it’s perfect for business events and offers a glimpse into the area's rich history.
  • Harbor Park: Enjoy family-friendly activities at Harbor Park, an urban oasis along the waterfront. This park is ideal for outdoor fun, featuring walking paths, picnic areas, and picturesque views of the Connecticut River.

Best time to go to Middletown

The best time to visit Middletown is dependant on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January29.1°F (-1.6°C)Light RainMostly SunnyAverageSlightly Low
February30.6°F (-0.8°C)Light RainMostly SunnyAverageSlightly Low
March37.8°F (3.2°C)Light RainMostly SunnyAverageAverage
April48.7°F (9.3°C)Light RainMostly SunnyAverageAverage
May59.2°F (15.1°C)Light RainMostly SunnyAverageSlightly High
June67.5°F (19.7°C)Light RainMostly SunnySlightly HighSlightly High
July74.3°F (23.5°C)Light RainMostly SunnySlightly HighAverage
August72.5°F (22.5°C)Light RainMostly SunnyAverageAverage
September65.5°F (18.6°C)Light RainMostly SunnySlightly HighAverage
October54.9°F (12.7°C)Light RainMostly SunnySlightly LowSlightly High
November43.3°F (6.3°C)Light RainMostly SunnySlightly LowAverage
December35.2°F (1.8°C)Light RainMostly SunnySlightly LowSlightly Low

Tips to save on your trip to Middletown

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling to Middletown during the low season (December to February) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Middletown Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Bradley Intl. Airport (BDL)
Population
46,800
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Brownstone Exploration & Discovery Park, Goodspeed Opera House and Dinosaur State Park

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Frequently asked questions

How much does a Middletown vacation package cost?
You'll find cheap prices from $296 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?
You're likely to find reduced prices and greater availability in November, December and January. Check out our cheap Middletown vacation packages and you could score some great off-season discounts.
How many days is enough for Middletown?
We recommend booking a Middletown vacation for at least 2 days. This will give you plenty of time to tick off popular sights such as Van Vleck Observatory and Wesleyan University, as well as explore neighborhoods like Main Street Historic District and Washington Street Historic District. You could even slot in a day trip beyond Middletown.
Is it worth booking a vacation package to Middletown?
Popular for its family-friendly attractions, festivals and history, a Middletown vacation offers something for everyone. Be sure to visit main sights like Artfarm and Kidcity Children's Museum, and consider renting a car for day trips to discover 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.
Does Expedia offer Book Now, Pay Later Middletown vacation packages?
Your Middletown getaway should be a relaxing escape from your busy life, not a source of money worries. So to give you a little more flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.

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