Middletown Vacation Packages 2025/2026 from $417

Middletown flight + hotel vacation packages

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

Best Western Hartford Hotel & Suites

South Meadows

$417

per person

Oct 23 - Oct 26

found 9 hours ago

Roundtrip flight included

San Juan (SJU) to Hartford (BDL)

This hotel features a gym and a seasonal outdoor pool. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. A 24-hour business center, a terrace, and a garden are also on offer.

DoubleTree by Hilton Hartford Downtown

Downtown Hartford

Save 100% on your flight

$722

per person

Oct 23 - Oct 26

found 9 hours ago

Roundtrip flight included

San Juan (SJU) 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.

Holiday Inn Express Vernon - Manchester by IHG

$462

per person

Oct 23 - Oct 26

found 9 hours ago

Roundtrip flight included

San Juan (SJU) 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.

Fairfield Inn & Suites Hartford Manchester

$464

per person

Oct 23 - Oct 26

found 9 hours ago

Roundtrip flight included

San Juan (SJU) 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.

Courtyard by Marriott Hartford Manchester

$445

per person

Oct 23 - Oct 26

found 9 hours ago

Roundtrip flight included

San Juan (SJU) 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 gym and conveniences like a 24-hour front desk and laundry facilities.

Top Middletown hotels deals

Inn at Middletown

70 Main Street, Middletown, CT

Free Cancellation

Reserve now, pay when you stay

$244 nightly

$278 total

Aug 21 - Aug 22

Total includes 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

The Capitol Hotel

440 Asylum St, Hartford, CT

Free Cancellation

Reserve now, pay when you stay

$84 nightly

$97 total

Aug 21 - Aug 22

Total includes 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

$159 nightly

$183 total

Sep 2 - Sep 3

Total includes taxes and fees

This smoke-free hotel features 2 restaurants, a bar/lounge, and a 24-hour gym. 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

Motel 6 New Haven - Branford, CT

320 E Main St, Branford, CT

Free Cancellation

$73 nightly

$84 total

Sep 3 - Sep 4

Total includes 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

Holiday Inn Express Southington by IHG

120 Laning St, Southington, CT

Free Cancellation

$104 nightly

$120 total

Aug 31 - Sep 1

Total includes taxes and fees

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.

Pool

Breakfast included

New Haven Hotel

229 George Street, New Haven, CT

Free Cancellation

Reserve now, pay when you stay

$135 nightly

$155 total

Sep 1 - Sep 2

Total includes 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

Don't see what you're looking for?

See all available properties in Middletown

View all properties

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.

Middlesex Hospital

Though Middlesex Hospital might be what brings you to town, perhaps you'll have a chance to explore more of Middletown while you are here.

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 $417. 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.