Madison Vacations

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Your Madison Vacation

The easiest way to experience this exciting city is with a custom-made Madison vacation package. Base yourself in the neighborhood of Downtown Cambridge, which is good for bars and pubs, culture and cafes or go someplace else — our packages are all about you. There's plenty to put on your must-see list during a trip to Madison, beginning with leading attractions such as Harriet Tubman Underground Railroad National Historical Park and Spocott Windmill. Whatever your travel plans or budget, organizing your ultimate tailored Madison vacation is easy with Expedia.

Discover the most popular places to visit in Madison

Cambridge

Harriet Tubman Underground Railroad National Historical Park

Learn about one of the key figures in the historic freedom of enslaved people in this park and visitor center.

Harriet Tubman Underground Railroad National Historical Park

Madison Hotel Deals

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd Cambridge MD
Fully refundableReserve now, pay when you stay
$203 nightly
The price is $231 total per night from Jan 19 to Jan 20
$231 total
Jan 19 - Jan 20
Total with taxes and fees
8.6/10 Excellent! (1,007 reviews)
Great rooms, amenities, staff

Reviewed on Dec 29, 2025

Hyatt Regency Chesapeake Bay
Rod 'N' Reel Resort

Rod 'N' Reel Resort

4 out of 5
4165 Mears Ave Chesapeake Beach MD
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $113 total per night from Jan 19 to Jan 20
$113 total
Jan 19 - Jan 20
Total with taxes and fees
8.4/10 Very Good! (1,000 reviews)
Clean room

Reviewed on Jan 4, 2026

Rod 'N' Reel Resort
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

3 out of 5
22769 Three Notch Rd California MD
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $109 total per night from Feb 2 to Feb 3
$109 total
Feb 2 - Feb 3
Total with taxes and fees
7.6/10 Good! (1,000 reviews)
Very nice clean comfortable rooms. The gentlemen that does the breakfast did a great job. Plenty of food, clean atmosphere and well stocked.

Reviewed on Jan 4, 2026

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
See all 548 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
Top Sights
Bill Burton Fishing Pier State Park, Cove Point Lighthouse and Choptank River Lighthouse

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Frequently asked questions

How much does a Madison vacation package cost?
You can pick up a vacation package to this popular destination on Expedia. But 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?
If you're looking to snag a cheap Madison vacation package, consider traveling in November, December and January. You're likely to find lower prices on flights and hotels during these months — ideal for travelers wishing to save money.
How many days is enough for Madison?
The ideal duration for your Madison vacation depends on what you'd like to see. Generally, a handful of days to a week will give you enough time to tick off all the major attractions and explore some hidden spots along the way.
How to find the best Madison package deals?
Use Expedia's handy filters to find some unbeatable Madison package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or browse for Madison package deals in the off-season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a Madison vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll usually score a better deal than booking each component individually. And you'll still have the flexibility to create a tailored Madison vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Madison?
If you're considering an impromptu Madison trip, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score amazing deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Madison vacation packages?
If you're anything like us, you love discovering new places but don't love the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the total cost of your Madison vacation across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.