Middletown Vacation Packages 2025 from $327

Middletown flight + hotel vacation packages

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

Americas Best Value Inn Torrington CT

Save 100% on your flight

per person

Aug 28 - Sep 1

found 20 hours ago

Roundtrip flight included

Orlando (MCO) to Hartford (BDL)

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. There's a gym on site, and a 24-hour front desk and a garden are also provided.

Solano Inn

Save 100% on your flight

per person

Aug 28 - Sep 1

found 20 hours ago

Roundtrip flight included

Orlando (MCO) to Hartford (BDL)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A picnic area, express check-out, and laundry facilities are also on offer.

DoubleTree by Hilton Hartford Downtown

Downtown Hartford

per person

Jul 24 - Jul 27

found 16 hours ago

Roundtrip flight included

Atlanta (ATL) to Hartford (BDL)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Self parking, a coffee shop, and a snack bar/deli are also offered.

Delamar West Hartford

Save 100% on your flight

per person

Jul 24 - Jul 27

found 16 hours ago

Roundtrip flight included

Atlanta (ATL) 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.

Hilton Garden Inn Hartford South/Glastonbury

per person

Jul 24 - Jul 27

found 16 hours ago

Roundtrip flight included

Atlanta (ATL) to Hartford (BDL)

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

Top Middletown hotels deals

Inn at Middletown

70 Main Street, Middletown, CT

Free Cancellation

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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

The Capitol Hotel

440 Asylum St, Hartford, CT

Free Cancellation

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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

New Haven Hotel

229 George Street, New Haven, CT

Free Cancellation

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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

Clarion Inn

201 Washington Avenue, North Haven, CT

Free Cancellation

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

Pool

Breakfast included

Motel 6 New Haven - Branford, CT

320 E Main St, Branford, CT

Free Cancellation

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A restaurant, free self parking, and a 24-hour front desk are among this motel's amenities. WiFi in public areas is free. A snack bar/deli is also provided.

Pet friendly

Parking included

Courtyard by Marriott Waterbury Downtown

63 Grand St, Waterbury, CT

Free Cancellation

Reserve now, pay when you stay

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This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Self parking, a 24-hour business center, and a coffee shop are also offered.

Free WiFi

Restaurant

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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

Wesleyan University

4/5(89 reviews)

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

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.

Harbor Park

4/5(5 reviews)

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.

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 $327. 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.