Middletown Vacation Packages

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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.

Top Middletown Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Motel 6 Windsor Locks, CT - Hartford

Motel 6 Windsor Locks, CT - Hartford

2 out of 5
per person
Sep 3 - Sep 5
found 9 hours ago
Roundtrip flight included
Calgary (YYC) to Hartford (BDL)
6.6/10 (1,018 reviews)
The place looks great, the areas very cleaned, great place to stay.

Reviewed on Jul. 31, 2025

Fairfield Inn & Suites Hartford Manchester

Fairfield Inn & Suites Hartford Manchester

2.5 out of 5
per person
Sep 3 - Sep 5
found 9 hours ago
Roundtrip flight included
Calgary (YYC) to Hartford (BDL)
8.6/10 Excellent! (998 reviews)
Will difinitely going back

Reviewed on Aug. 1, 2025

Comfort Inn Wethersfield - Hartford

Comfort Inn Wethersfield - Hartford

2.5 out of 5
per person
Sep 3 - Sep 5
found 9 hours ago
Roundtrip flight included
Calgary (YYC) to Hartford (BDL)
6/10 (1,002 reviews)
I like the professionalism of the staff

Reviewed on Aug. 4, 2025

Howard Johnson by Wyndham Hartford South – Rocky Hill

Howard Johnson by Wyndham Hartford South – Rocky Hill

2 out of 5
per person
Sep 3 - Sep 5
found 9 hours ago
Roundtrip flight included
Calgary (YYC) to Hartford (BDL)
8.2/10 Very Good! (1,001 reviews)
Nice remodeled hotel. Meets all the needs and beds were comfy.

Reviewed on Jul. 21, 2025

Ramada by Wyndham Hartford North / Bradley Airport

Ramada by Wyndham Hartford North / Bradley Airport

2.5 out of 5
per person
Sep 3 - Sep 5
found 9 hours ago
Roundtrip flight included
Calgary (YYC) to Hartford (BDL)
6.6/10 (794 reviews)
Looks abandoned from outside. Lobby very nice, has pool. Hallways dark, carpet desperately needs vacuum. Baseboards gross. Bathroom: showerhead, good pressure but bestfor somone under 5ft tall. Toilet from kindergarten. Stained ceiling. Room: bed averge, shhets clean. Looks like they tried to upgrade, but bug patch in ceiling and on wall. Sliding glass doors are green, curtains filthy. Outside: garbage, dirty diapers, cigarette butts, plastic bottles...lawn not mowed. Door has cobwebs and cracked glass...dumpster full and overflowing. Will not stay.there again. Have pictures.

Reviewed on Aug. 2, 2025

Ready to book your vacation to Middletown?

 

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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
The price is CA $258 per night from Aug 5 to Aug 6
CA $258
CA $324 total
Aug 5 - Aug 6
includes taxes & fees
8.8/10 Excellent! (495 reviews)
Good location
"Very nice hotel in great location"

Reviewed on Jul. 30, 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
The price is CA $105 per night from Aug 24 to Aug 25
CA $105
CA $121 total
Aug 24 - Aug 25
includes taxes & fees
7.4/10 Good! (1,009 reviews)
"I like the area as being across from the Capitol. Great hotel to stay at especially if your attending any activity across the way. Staff was also very nice and helpful."

Reviewed on Aug. 3, 2025

The Capitol 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 CA $219 per night from Aug 24 to Aug 25
CA $219
CA $252 total
Aug 24 - Aug 25
includes taxes & fees
8.2/10 Very Good! (1,011 reviews)
"Nice hotel and great location."

Reviewed on Aug. 4, 2025

Omni New Haven Hotel at Yale
See all 1,156 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 Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Middletown vacation package cost?
You can grab a vacation package to this destination from CA $819 on Expedia. However, how much your vacation to Middletown costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Middletown?
December, January and February are great times to look for cheap Middletown vacation packages. Choosing to travel in less busy periods means you'll typically find reduced prices on hotels and flights.
How many days is enough for Middletown?
To get the most out of your Middletown vacation, we recommend staying for 2 days. Split your time between discovering Dinosaur State Park, Lake Beseck Beach and other well-known attractions, as well as exploring neighbourhoods like Main Street Historic District and Washington Street Historic District. If you've got some spare time, add a day trip or tour to your Middletown vacation itinerary.
Is it worth booking a vacation package to Middletown?
Whether you're looking to explore top sights such as Artfarm and General Mansfield House on your Middletown vacation, or coming for its great family-friendly attractions, festivals and history, there's something for everyone here. With so much to see and do, you'll soon learn why so many people think Middletown is a good vacation destination.
How to find the best Middletown package deals?
Use Expedia's handy filters to find some fabulous Middletown package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Middletown package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Middletown vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component separately. And you'll still enjoy the flexibility to create a tailored Middletown vacation by choosing your favourite airline, accommodation type and car class.
When to book a vacation package to Middletown?
Score fantastic discounts by booking your flights ahead of time with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for a spur-of-the-moment Middletown escape.
How to plan a trip to Middletown?

  1. Pick your travel dates: The things you plan to do in Middletown and your preferred season can help you decide when to travel.
  2. Set a budget: Consider expenses such as flights, transportation and food when working out how much to save for your trip to Middletown. Then, pick a property that fits your budget, whether that's an affordable option or a deluxe retreat.
  3. Decide how long to go away for: Now that you know more about Middletown, you can work out the ideal length of your break. Put together a draft itinerary and give yourself enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a tailored Middletown vacation package.

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