Madison Vacation Packages 2026 from $649

Madison flight + hotel vacation packages

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

Quality Suites Stratford

$649

per person

Oct 9 - Oct 12

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to New Haven (HVN)

A golf course and a gym are featured at this smoke-free hotel. 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.

Beechmont - Perfect for Family Retreat!

North End

$1,021

per person

Aug 29 - Aug 31

found 22 hours ago

Roundtrip flight included

Los Angeles (LAX) 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.

Top Madison hotels deals

Madison Beach Hotel

94 West Wharf Road Madison CT

$479 nightly

$551 total

Aug 23 - Aug 24

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

$72 nightly

$83 total

Aug 2 - Aug 3

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

Holiday Inn Express Southington by IHG

120 Laning St Southington CT

Free Cancellation

$91 nightly

$104 total

Aug 2 - Aug 3

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

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT

Free Cancellation

$100 nightly

$115 total

Jul 30 - Jul 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

New Haven Hotel

229 George Street New Haven CT

Free Cancellation

Reserve now, pay when you stay

$135 nightly

$155 total

Aug 9 - Aug 10

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

Sound View Greenport

58775 County Rd 48 Greenport NY

$388 nightly

$443 total

Aug 18 - Aug 19

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.

Stay near popular Madison attractions

A rural landscape with a large fallen tree in the foreground, fields, and a forest in the background.

Hammonasset Beach State Park

8.8/10 (137 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.

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Frequently asked questions

How much are vacation packages to Madison?

Travelocity provides flight and hotel vacation packages starting as low as $649. 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.