Madison Vacations

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Your Madison Vacation

Reserve a Madison vacation package that includes everything you need and no unnecessary extras. Great for walking, hiking and views, think about basing yourself in the neighborhood of Essex Village. Hammonasset Beach State Park, Hammonasset Beach and Meigs Point Nature Center are just a few of the many sights worth checking out during your trip to Madison. That dream Madison vacation is a few clicks away. Explore airfares, hotels and more on Expedia for a trip that's tailored just for you.

Discover the most popular places to visit in Madison

Looks a little like out of Africa

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 State Park

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.

North Madison Shopping Center

Meigs Point Nature Center

Enjoy the collegiate vibe at Meigs Point Nature Center during your stay in Madison. While you're in the area, stroll along the beautiful beaches.

Meigs Point Nature Center

Madison Hotel Deals

Madison Beach Hotel

Madison Beach Hotel

4 out of 5
94 West Wharf Road Madison CT
$244 nightly
The price is $281 total per night from Jan 1 to Jan 2
$281 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
9.4/10 Exceptional! (340 reviews)
Great overall service.

Reviewed on Dec 12, 2025

Madison Beach Hotel
New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
$97 nightly
The price is $112 total per night from Dec 28 to Dec 29
$112 total
Dec 28 - Dec 29
Total with taxes and fees
9/10 Wonderful! (1,924 reviews)
Very clean, convenient parking across the street from the hotel. The staff were very friendly and helpful.

Reviewed on Dec 14, 2025

New Haven Hotel
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
20 Dwight Street New Haven CT
Fully refundable
$110 nightly
The price is $127 total per night from Jan 11 to Jan 12
$127 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
8.6/10 Excellent! (992 reviews)
Yes very nice

Reviewed on Dec 14, 2025

Cambria Hotel New Haven University Area
See all 1,938 properties in Madison
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.

Find the Best Madison Vacation Packages

Madison Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Tweed - New Haven Regional Airport (HVN)
Population
19,100
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Hammonasset Beach State Park, Hammonasset Beach and Stony Creek Museum

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Frequently asked questions

How much does a Madison vacation package cost?
You can grab a vacation package to this top destination on Expedia. However, how much your vacation to Madison costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Madison?
November, December and January are great times to search for cheap Madison vacation packages. Traveling in less busy periods means you'll typically find lower prices on flights and hotels.
How many days is enough for Madison?
You can see all the major attractions in Madison in a few days, including the must-see Allis-Bushnell House and Museum. If you're looking for a longer Madison vacation, check out which kind of excursions and activities are available nearby.
Is it worth booking a vacation package to Madison?
Well known for its cafes, dining and a host of other highlights, you can be assured Madison is a good vacation destination. Some of the top attractions to stick on your to-do list? Don't miss Hammonasset Beach State Park and Scranton Memorial Library during your Madison vacation.
How to find the best Madison package deals?
Use Expedia's filters to find some of the best Madison package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or look for Madison package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Madison vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll typically snag a better deal than booking each component individually. And you'll still get the freedom to create a personalized Madison vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Madison?
Score incredible bargains by reserving your flights in advance with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for a spur-of-the-moment Madison getaway.
Does Expedia offer Book Now, Pay Later Madison vacation packages?
Your Madison break should be an escape from your busy life, not a source of money worries. So to allow you more flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.