Middletown Vacation Packages 2026 from $568

Middletown flight + hotel vacation packages

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

Two Trees Inn

$568

per person

Oct 1 - Oct 6

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Hartford (BDL)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the hot tub and free perks like continental breakfast and free self parking.

Holiday Inn Express Southington by IHG

$616

per person

Nov 3 - Nov 10

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) 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.

Hilton Garden Inn Hartford South/Glastonbury

$850

per person

Nov 3 - Nov 10

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) 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.

Residence Inn by Marriott Southington

$738

per person

Nov 3 - Nov 10

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Hartford (BDL)

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

Avon Old Farms Hotel

$746

per person

Sep 28 - Oct 1

found 1 day ago

Roundtrip flight included

Minneapolis (MSP) to Hartford (BDL)

This hotel features an outdoor pool, a 24-hour gym, and a restaurant. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and WiFi in public areas. You'll appreciate the sauna, bar/lounge, and wedding services.

Top Middletown hotels deals

Inn at Middletown

70 Main Street Middletown CT

Free Cancellation

Reserve now, pay when you stay

$190 nightly

$215 total

Sep 7 - Sep 8

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

$127 nightly

$146 total

Sep 7 - Sep 8

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

Motel 6 New Haven - Branford, CT

320 E Main St Branford CT

Free Cancellation

$72 nightly

$83 total

Sep 1 - Sep 2

Total with taxes and fees

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

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

Free Cancellation

$83 nightly

$95 total

Aug 30 - Aug 31

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. A picnic area is also provided.

Pet friendly

Parking included

Water's Edge Resort & Spa

1525 Boston Post Road Westbrook CT

Free Cancellation

Reserve now, pay when you stay

$266 nightly

$306 total

Aug 31 - Sep 1

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.

On private beach

Pool

The Capitol Hotel

440 Asylum St Hartford CT

Free Cancellation

Reserve now, pay when you stay

$105 nightly

$121 total

Aug 30 - Aug 31

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

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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.

Stay near popular Middletown attractions

A large white building with columns and a central staircase.

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.

See properties

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 $568. 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.