Madison Vacation Packages 2025/2026 from $249

Madison flight + hotel vacation packages

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

Motel 6 Southington, CT - Hartford

$249

per person

Nov 14 - Nov 17

found 11 hours ago

Roundtrip flight included

Orlando (MCO) to New Haven (HVN)

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A snack bar/deli is provided and the front desk is staffed around-the-clock.

Holiday Inn Express Southington by IHG

$257

per person

Nov 14 - Nov 17

found 11 hours ago

Roundtrip flight included

Orlando (MCO) to New Haven (HVN)

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.

Courtyard by Marriott Southington

$291

per person

Nov 14 - Nov 17

found 11 hours ago

Roundtrip flight included

Orlando (MCO) to New Haven (HVN)

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a garden, and dry cleaning are also offered.

Hilton Garden Inn Hartford North/Bradley Int'l Airport

$511

per person

Oct 16 - Oct 20

found 1 day ago

Roundtrip flight included

Washington (IAD) to New Haven (HVN)

This hotel features a restaurant, a 24-hour gym, 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 free perks like free self parking and an area shuttle.

Residence Inn by Marriott Southington

$306

per person

Nov 14 - Nov 17

found 11 hours ago

Roundtrip flight included

Orlando (MCO) to New Haven (HVN)

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.

Top Madison hotels deals

Madison Beach Hotel

94 West Wharf Road, Madison, CT

$427 nightly

$491 total

Sep 4 - Sep 5

Total with taxes and fees

This smoke-free hotel features a private beach, a full-service spa, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Enjoy the gym and perks like free WiFi.

On private beach

Spa

Motel 6 New Haven - Branford, CT

320 E Main St, Branford, CT

Free Cancellation

$74 nightly

$85 total

Aug 27 - Aug 28

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

Best Western Executive Hotel Of New Haven - West Haven

490 Saw Mill Rd, West Haven, CT

Free Cancellation

Reserve now, pay when you stay

$105 nightly

$120 total

Aug 25 - Aug 26

Total with taxes and fees

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

Pool

Breakfast included

Omni New Haven Hotel at Yale

155 Temple St, New Haven, CT

Free Cancellation

Reserve now, pay when you stay

$143 nightly

$165 total

Sep 21 - Sep 22

Total with 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

Cambria Hotel New Haven University Area

20 Dwight Street, New Haven, CT

Free Cancellation

Reserve now, pay when you stay

$118 nightly

$136 total

Sep 4 - Sep 5

Total with taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a lobby fireplace, and a computer station are also offered.

Pet friendly

Free WiFi

Holiday Inn Express Southington by IHG

120 Laning St, Southington, CT

Free Cancellation

$108 nightly

$124 total

Aug 24 - Aug 25

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.

Pool

Breakfast included

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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

Hammonasset Beach State Park

4.5/5(84 reviews)

You can take time to visit Hammonasset Beach State Park during your travels to Madison. While you're in the area, stroll along the beautiful beaches.

Hammonasset Beach

Why not spend a lazy afternoon at Hammonasset Beach during your trip to Madison? While you're in the area, stroll along the beaches.

North Madison Shopping Center

You can search for that perfect souvenir at North Madison Shopping Center during your trip to Madison. While you're in the area, wander around the natural setting.

Frequently asked questions

How much are vacation packages to Madison?

Travelocity provides flight and hotel vacation packages starting as low as $249. With such amazing bargains, you'll be exploring all of Madison in no time.

How long should my Madison vacation be?

Around 2 nights is the average amount of time travelers vacation in Madison. But how long is right for you all depends on how many magical memories you want to create. Why not stay a couple of extra days and discover some hidden treasures?

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

Picking up the perfect package deal to Madison couldn't be easier with Travelocity. With around 400 partner airlines and 1,000,000 properties worldwide, you're flush with choice when it comes to picking your flights and hotels.

Why should I book my Madison vacation bundle via Travelocity?

From our 24/7 customer support to our range of amazing destinations, we're committed to giving you the vacation of a lifetime. All you'll have to do is to click and book — our Price Match Guarantee will make sure you lock in the best price.

Can I save on my Madison car rental if I combine it with my hotel or flight?

With a Madison vacation package, you can bundle your hotel, car and flight bookings and save loads. If you'd love to discover the best of this impressive location, why not make a beeline for Times Square? This renowned attraction is 85 mi from Madison. With a rental car, you'll be there in a flash.

Which airport is best for Madison?

Bradley Intl. Airport (BDL) is one of the top airports for Madison. You'll find it 45 mi north of the buzzing city center. Your other choices are MacArthur Airport (ISP) (45 mi away from central Madison) and Tweed - New Haven Regional Airport (HVN) (17 mi away from central Madison).

What is there to do in Madison?

While veering off the tourist trail is rewarding, you really shouldn't miss the popular attractions that make a place famous. Hammonasset Beach State Park and Hammonasset Beach are just two of them in Madison.

Where should I stay when visiting Madison?

If you're searching for someplace comfortable to base yourself, consider the The Homestead. It's the top pick for many travelers.