Madison Vacations from $416

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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.

The Latest Madison vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
Save 100% on your flight
Price was $625, price is now $416 per person
$416
per person
Feb 14 - Feb 21
found 15 hours ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
8.6/10 Excellent! (1,149 reviews)
Staff is friendly room is clean.

Reviewed on Nov 30, 2025

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Save 100% on your flight
Price was $2,762, price is now $1,620 per person
$1,620
per person
Jan 1 - Jan 6
found 8 hours ago
Roundtrip flight included
Los Angeles (LAX) to New Haven (HVN)
No reviews
Residence Inn by Marriott Southington

Residence Inn by Marriott Southington

3 out of 5
Save 100% on your flight
Price was $746, price is now $499 per person
$499
per person
Feb 14 - Feb 21
found 15 hours ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
8.6/10 Excellent! (581 reviews)
Room was clean, staff was super friendly. Only problem was the nozzle on the bath tub it was dripping the entire stay

Reviewed on Nov 30, 2025

Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
Price was $682, price is now $508 per person
$508
per person
Feb 14 - Feb 21
found 15 hours ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
8.8/10 Excellent! (1,004 reviews)
This hotel was clean which was great because I booked the wrong hotel I thought this was the one I stayed at before but it was the Marriott across from it. I was glad that it ended up being clean or I probably would’ve asked to cancel my reservation because this is the second Hilton. I’ve stayed in and they are so dated. It’s sad like spend some money and fix them up because you would think you’re booking at a Hilton and it should be nice and literally they’re old and rundown and it’s very sad. The only reason why I gave a four star for cleanliness was because it was clean. If you are looking for a nice bougie hotel room and hotel, this is not the place book across the street at the Marriott or the Hyatt.

Reviewed on Nov 24, 2025

Residence Inn by Marriott Hartford/Windsor

Residence Inn by Marriott Hartford/Windsor

3 out of 5
Price was $626, price is now $472 per person
$472
per person
Feb 14 - Feb 21
found 15 hours ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
8.2/10 Very Good! (656 reviews)
The room was clean spacious just what we needed for pur family for Thanksgiving. Made our day extra special

Reviewed on Dec 1, 2025

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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
Fully refundableReserve now, pay when you stay
$245 nightly
The price is $282 total per night from Dec 7 to Dec 8
$282 total
Dec 7 - Dec 8
Total with taxes and fees
9.4/10 Exceptional! (338 reviews)
Great 1st wedding anniversary experience!

Reviewed on Nov 13, 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
$74 nightly
The price is $85 total per night from Dec 25 to Dec 26
$85 total
Dec 25 - Dec 26
Total with taxes and fees
9/10 Wonderful! (1,907 reviews)
Convenient location for visiting Yale. The hotel lobby area is nice for spending time outside of room when travelling with a family oe friends.

Reviewed on Nov 29, 2025

New Haven Hotel
Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
320 E Main St Branford CT
Fully refundable
$74 nightly
The price is $85 total per night from Dec 5 to Dec 6
$85 total
Dec 5 - Dec 6
Total with taxes and fees
7/10 Good! (1,008 reviews)
Stay here because it’s clean and the price is right for the money you can’t beat it plus you have excellent food at Capones restaurant 100 feet away for your convenience

Reviewed on Nov 25, 2025

Motel 6 New Haven - Branford, CT
See all 1,928 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 from $416 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.