Deals on vacations and trips to Middletown

Save when you book Middletown package deals

Choose two or more items and save on your trip:

Middletown flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Rodeway Inn Willington North

Rodeway Inn Willington North

2 out of 5
Price was $174, price is now $139 per person
$139
per person
Feb 26 - Mar 1
found 3 hours ago
Roundtrip flight included
Orlando (MCO) to Hartford (BDL)
This hotel features 2 restaurants and a gym. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy a meal in one of the 4 coffee shops/cafes and perks like free continental breakfast and free self parking.
Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

3 out of 5
Save 100% on your flight
Price was $267, price is now $203 per person
$203
per person
Feb 26 - Mar 1
found 3 hours ago
Roundtrip flight included
Orlando (MCO) to Hartford (BDL)
This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the in-room fitness and perks like free self parking.
Fairfield Inn & Suites Hartford Manchester

Fairfield Inn & Suites Hartford Manchester

2.5 out of 5
Save 100% on your flight
Price was $315, price is now $245 per person
$245
per person
Feb 26 - Mar 1
found 3 hours ago
Roundtrip flight included
Orlando (MCO) 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.
DoubleTree by Hilton Hartford - Bradley Airport

DoubleTree by Hilton Hartford - Bradley Airport

4 out of 5
Price was $278, price is now $229 per person
$229
per person
Feb 26 - Mar 1
found 3 hours ago
Roundtrip flight included
Orlando (MCO) 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, free WiFi in public areas, and free airport shuttle. Enjoy the 24-hour gym and perks like free self parking.
Americas Best Value Inn Torrington CT

Americas Best Value Inn Torrington CT

2.5 out of 5
Price was $244, price is now $201 per person
$201
per person
Feb 26 - Mar 1
found 3 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.

Top Middletown hotels deals

Inn at Middletown

Inn at Middletown

3.5 out of 5
70 Main Street Middletown CT
Free Cancellation
Reserve now, pay when you stay
$201 nightly
The price is $228 total per night
$228 total
Jan 12 - Jan 13
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.
New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
Free Cancellation
Reserve now, pay when you stay
$109 nightly
The price is $126 total per night
$126 total
Jan 25 - Jan 26
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.
The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St Hartford CT
Free Cancellation
Reserve now, pay when you stay
$88 nightly
The price is $102 total per night
$102 total
Jan 8 - Jan 9
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.
Hampton Inn & Suites Hartford/East Hartford

Hampton Inn & Suites Hartford/East Hartford

2.5 out of 5
351 Pitkin Steet East Hartford CT
$98 nightly
The price is $112 total per night
$112 total
Jan 30 - Jan 31
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. A 24-hour business center, a lobby fireplace, and express check-in are also on offer.
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St Southington CT
Free Cancellation
$89 nightly
The price is $102 total per night
$102 total
Feb 6 - Feb 7
Total with 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.
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
155 Temple St New Haven CT
Free Cancellation
Reserve now, pay when you stay
$149 nightly
The price is $172 total per night
$172 total
Feb 1 - Feb 2
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.
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

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

Wesleyan University

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.

Wadsworth Mansion

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.

Middlesex Hospital

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 $139. 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.

Photos of local treasures

Browse Middletown vacation photos for more inspiration

Photo by Simmie Reagor
Photo by Simmie Reagor
Photo by Tiffany Zhou
Photo by Tiffany Zhou
Photo by mark MacGregor
Photo by mark MacGregor

Explore More Ways to Travel with Travelocity