Madison Vacations from $562
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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.
The Latest Madison vacation packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Hotel & Suites Harrington-Dover area, DE by IHG
$584
per person
Dec 27 - Jan 2
found 11 hours ago
Roundtrip flight included
San Juan (SJU) to Salisbury (SBY)
9/10 Wonderful! (1,005 reviews)
Room was mostly clean but definitely had a pet odor in it. We had to burn candles to lessen the odor when we were in the room. Had an issue when we had to extend our trip a day because we had used Expedia. We were able to get another reservation and spoke directly to the front desk about staying in the same room and not being disturbed. (This was a working trip and we had been up almost 26 hours which is why we wanted everything set when we got to the hotel to sleep) We were guaranteed everything was set. The next morning housekeeping knocked on our door (waking us up) and then about 30 minutes later the front desk called, waking us up a second time. They apologized, but that isn’t much of a consolation when all you needed was sleep.
Parking was great, and staff were nice. The breakfast was also good.
Reviewed on Oct 4, 2026
Stay near popular Madison attractions
Harriet Tubman Underground Railroad National Historical Park
9.6/10 (95 reviews)
Learn about one of the key figures in the historic freedom of enslaved people in this park and visitor center.
Madison Hotel Deals
St Michaels Inn
1228 S Talbot Street St. Michaels MD
Fully refundableReserve now, pay when you stay
$95 nightly
$105 total
Nov 1 - Nov 2
Total with taxes and fees
8/10 Very Good! (1,004 reviews)
"We travel to St micheals md, several times a year, during the oyster season. Usually we stay at hotels in easton, so this time we tried the st micheals inn. It's closer to the Cheasapeake Landing restaurant. We were placed in a room opposite the main street, which made for a very quiet evening. Much ..."
Reviewed on Oct 10, 2026
Rod 'N' Reel Resort
4165 Mears Ave Chesapeake Beach MD
Fully refundableReserve now, pay when you stay
$132 nightly
$146 total
Oct 21 - Oct 22
Total with taxes and fees
8.6/10 Excellent! (1,006 reviews)
"Beautiful facility with a lot of potential, but the service was just okay. The staff seemed somewhat disengaged, The bathroom also could have been cleaner, particularly around the sink. Overall, a nice setting, but the service and cleanliness could be better."
Reviewed on Oct 11, 2026
avid hotel California - Lexington Park by IHG
23274 Three Notch Road California MD
Fully refundable
$97 nightly
$108 total
Oct 28 - Oct 29
Total with taxes and fees
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 from $562 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.
