Madison Vacations from $454

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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.
Hampton Inn Milford

Hampton Inn Milford

2.5 out of 5
Save 100% on your flight
Price was $581, price is now $454 per person
$454
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8/10 Very Good! (1,001 reviews)
Free breakfast. Day I checked out....they said systems were down...so no breakfast. Didn't under what that had to do with breakfast.

Reviewed on Aug 16, 2025

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Save 100% on your flight
Price was $2,637, price is now $1,607 per person
$1,607
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
No reviews
Madison Beach Hotel

Madison Beach Hotel

4 out of 5
Madison Center
Save 100% on your flight
Price was $1,356, price is now $973 per person
$973
per person
Nov 7 - Nov 12
found 9 hours ago
Roundtrip flight included
Miami (MIA) to New Haven (HVN)
9.4/10 Exceptional! (312 reviews)
The hotel is beautiful and the grounds are wonderful. The staff was top notch. We will definitely stay again.

Reviewed on Aug 18, 2025

Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
West River
Save 100% on your flight
Price was $635, price is now $491 per person
$491
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.8/10 Excellent! (862 reviews)
Booking my next stay now!

Reviewed on Aug 24, 2025

Trumbull Marriott Shelton

Trumbull Marriott Shelton

3.5 out of 5
Save 100% on your flight
Price was $672, price is now $527 per person
$527
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.2/10 Very Good! (1,009 reviews)
The place was really nice. The room was very far from the only elevator which was inconvenient. The staff wasn't polite or personable

Reviewed on Aug 17, 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
$403 nightly
The price is $463 total per night from Sep 11 to Sep 12
$463 total
Sep 11 - Sep 12
Total with taxes and fees
9.4/10 Exceptional! (312 reviews)
"The hotel is beautiful and the grounds are wonderful. The staff was top notch. We will definitely stay again."

Reviewed on Aug 18, 2025

Madison Beach 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
$72 nightly
The price is $83 total per night from Sep 1 to Sep 2
$83 total
Sep 1 - Sep 2
Total with taxes and fees
6.8/10 (1,011 reviews)
"Great location, quiet & yet right near Rt 95. Clean, nice room, polite staff!!!"

Reviewed on Aug 25, 2025

Motel 6 New Haven - Branford, CT
Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
490 Saw Mill Rd, West Haven, CT
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $120 total per night from Aug 31 to Sep 1
$120 total
Aug 31 - Sep 1
Total with taxes and fees
7.8/10 Good! (1,305 reviews)
"Staff was very friendly and knowledgeable of the area."

Reviewed on Aug 22, 2025

Best Western Executive Hotel Of New Haven - West Haven
See all 1,910 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.

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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 $454 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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