Madison Vacation Packages 2026 from $423

Madison flight + hotel vacation packages

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

Pier Blue Inn Old Saybrook - Essex

Saybrook Manor

$423

per person

Jun 19 - Jun 21

found 22 hours ago

Roundtrip flight included

Fort Myers (RSW) to New Haven (HVN)

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 and barbecue grills are also provided.

Beechmont - Perfect for Family Retreat!

North End

Save 100% on your flight

$2,540

per person

Jul 1 - Jul 8

found 1 day ago

Roundtrip flight included

Miami (MIA) to New Haven (HVN)

This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a communal living room are also on offer.

Madison Beach Hotel

Madison Center

Save 100% on your flight

$1,048

per person

Jun 19 - Jun 21

found 22 hours ago

Roundtrip flight included

Fort Myers (RSW) to New Haven (HVN)

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.

Hyatus Luxury Residences City Crossing

The Hill

Save 100% on your flight

$1,367

per person

May 15 - May 17

found 1 day ago

Roundtrip flight included

Fort Lauderdale (FLL) to New Haven (HVN)

This aparthotel features a 24-hour gym and a seasonal outdoor pool. Traveling for business? Take advantage of the free WiFi in public areas, laundry service, and conference center. Enjoy the a rooftop terrace and perks like free self parking and a free area shuttle.

Clarion Inn North Haven - New Haven North

$562

per person

Jun 11 - Jun 15

found 1 day ago

Roundtrip flight included

Tampa (TPA) to New Haven (HVN)

A restaurant and a 24-hour gym are featured at this hotel. 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.

Top Madison hotels deals

Madison Beach Hotel

94 West Wharf Road Madison CT

$286 nightly

$329 total

Apr 27 - Apr 28

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

New Haven Hotel

229 George Street New Haven CT

Free Cancellation

Reserve now, pay when you stay

$107 nightly

$123 total

Apr 29 - Apr 30

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

Holiday Inn Express Southington by IHG

120 Laning St Southington CT

Free Cancellation

Reserve now, pay when you stay

$100 nightly

$115 total

Apr 19 - Apr 20

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

Omni New Haven Hotel at Yale

155 Temple St New Haven CT

Free Cancellation

Reserve now, pay when you stay

$161 nightly

$185 total

Apr 27 - Apr 28

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.

Pet friendly

Free WiFi

Water's Edge Resort & Spa

1525 Boston Post Road Westbrook CT

Free Cancellation

Reserve now, pay when you stay

$266 nightly

$305 total

Apr 22 - Apr 23

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

Sound View Greenport

58775 County Rd 48 Greenport NY

$228 nightly

$260 total

May 3 - May 4

Total with taxes and fees

A private beach and a restaurant are featured at this smoke-free hotel. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like continental breakfast and WiFi in public areas.

On private beach

Pool

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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

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.

A silhouette of a man standing on a jetty looking at the sunset.

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 $423. 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.