Middletown Vacation Packages 2026 from $589

Middletown flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Fairfield Inn & Suites Hartford Manchester

$589

per person

Jul 10 - Jul 12

found 1 day ago

Roundtrip non-stop flight included

Columbia (CAE) to Hartford (BDL)

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Holiday Inn Express Southington by IHG

$617

per person

Jun 6 - Jun 12

found 6 hours ago

Roundtrip flight included

Jacksonville (JAX) to Hartford (BDL)

This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Landing in Downtown Hartford Near Dunkin' Park

Downtown Hartford

$684

per person

Jun 6 - Jun 12

found 6 hours ago

Roundtrip flight included

Jacksonville (JAX) to Hartford (BDL)

This apartment features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, laundry facilities, and a virtual front desk are also on offer.

Hyatt Place Uncasville - Casino Area

$665

per person

Jun 6 - Jun 12

found 6 hours ago

Roundtrip flight included

Jacksonville (JAX) to Hartford (BDL)

This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy free perks like buffet breakfast and free self parking.

Delamar West Hartford

$734

per person

Jul 10 - Jul 12

found 1 day ago

Roundtrip non-stop flight included

Columbia (CAE) to Hartford (BDL)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Relax with a drink at the bar/lounge and enjoy perks like free valet parking and free WiFi. Free self parking, a 24-hour business center, and a terrace are also offered.

Top Middletown hotels deals

Inn at Middletown

70 Main Street Middletown CT

Free Cancellation

Reserve now, pay when you stay

$179 nightly

$203 total

Apr 29 - Apr 30

Total with taxes and fees

This hotel features an indoor pool, a hot tub, and a restaurant. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. Enjoy the gym and perks like free self parking.

Pool

Hot Tub

New Haven Hotel

229 George Street New Haven CT

Free Cancellation

Reserve now, pay when you stay

$112 nightly

$129 total

May 3 - May 4

Total with taxes and fees

A gym, self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services.

Pet friendly

Free WiFi

The Capitol Hotel

440 Asylum St Hartford CT

Free Cancellation

Reserve now, pay when you stay

$84 nightly

$97 total

Apr 27 - Apr 28

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free full breakfast and free WiFi. Traveling on business? Take advantage of the 2 conference rooms, business center, and express check-out. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.

Breakfast included

Pet friendly

Omni New Haven Hotel at Yale

155 Temple St New Haven CT

Free Cancellation

Reserve now, pay when you stay

$119 nightly

$137 total

May 25 - May 26

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Self parking, a coffee shop, and limo/town car service are also offered.

Pet friendly

Free WiFi

Holiday Inn Express Southington by IHG

120 Laning St Southington CT

Free Cancellation

Reserve now, pay when you stay

$100 nightly

$115 total

May 3 - May 4

Total with taxes and fees

Water's Edge Resort & Spa

1525 Boston Post Road Westbrook CT

Free Cancellation

Reserve now, pay when you stay

$264 nightly

$304 total

May 20 - May 21

Total with taxes and fees

This smoke-free resort features a private beach, a full-service spa, and 3 restaurants. Relax with beach cabanas and sun loungers, and cool off with a drink at the beachside bar. Enjoy the 2 outdoor tennis courts and perks like free valet parking and free WiFi.

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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.

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.

New England Seascape in New Haven Harbor in Connecticut at Sunrise: A tranquil beachfront along the Pardee Seawall Park

Harbor Park

Harbor Park is just one of the places to see in Middletown, so why not enjoy the other things to explore during your travels? Experience the area's festivals and entertainment venues.

Wesleyan University

Enjoy the collegiate vibe when you visit Wesleyan University, during your travels in Middletown. Experience the area's festivals or attend a sporting event.

Frequently asked questions

How much are vacation packages to Middletown?

With a Travelocity vacation package, you could paint the town red in Middletown from just $589. Activities, hotels and flights — we've got you covered. You'll save tons just by combining your bookings together. And with all that taken care of before you leave, you won't have to worry about a thing.

How long should my Middletown vacation be?

Many travelers secure a hotel for 2 nights in Middletown. But that doesn't necessarily mean you're limited to that. How long you spend here comes down to what sorts of things you want to do on your vacation. If you'd like to familiarize yourself with every inch of this awesome location, consider booking another few nights (or even longer!).

Where can I get the best vacation package deals for Middletown?

With at least 400 airline partners and 1,000,000 properties around the world, you can't beat Travelocity. Scroll through our extensive range and create the perfect Middletown vacation package. Don't you just love it when planning a trip is that easy?

Why should I book my Middletown vacation bundle with Travelocity?

Travel is all about making cherished memories and leaving all your stresses behind — which is why we have a team of experts available round-the-clock should you need them. On top of that, our Price Match Guarantee ensures you'll always get the best price available on our huge range of package deals. So what are you waiting for? There's no time like the present to secure that vacation you've always wanted.

Will I save money on my Middletown car rental if I book it with a hotel or flight?

With a Middletown vacation package, you can bundle your flight, car and hotel bookings and save some serious money. If you want to discover the best of this exciting part of the world, why not check out Times Square? This must-see sight is 90 mi from Middletown. With your own rental car, you'll be there in the blink of an eye.

Which airport is best for Middletown?

Bradley Intl. Airport (BDL) is one of the most popular airports in Middletown. It's roughly 25 mi north of the downtown area. Your other options are MacArthur Airport (ISP) (60 mi away from central Middletown) and Tweed - New Haven Regional Airport (HVN) (25 mi away from central Middletown).

What is there to do in Middletown?

While hopping off the tourist trail is no doubt rewarding, you shouldn't miss the popular sights that make a destination famous. Artfarm and General Mansfield House are a couple of them in Middletown.

Where should I stay when visiting Middletown?

If you're after somewhere to spend your nights, check out the Inn at Middletown. It's the top choice for many travelers.