Madison Vacations from $773

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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.
The Surf Shanty Motel

The Surf Shanty Motel

2.5 out of 5
Save 100% on your flight
Price was $1,076, price is now $773 per person
$773
per person
Jul 10 - Jul 14
found 9 hours ago
Roundtrip flight included
New York (NYC) to Salisbury (SBY)
9.8/10 Exceptional! (317 reviews)
Room was clean. Plenty of parking. Check in was confusing but we got in. Front desk employee was helpful with our TV.

Reviewed on May 10, 2026

The Americana Hotel

The Americana Hotel

2.5 out of 5
Downtown Ocean City
Price was $1,401, price is now $1,104 per person
$1,104
per person
Jul 13 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
8.6/10 Excellent! (1,180 reviews)
The room was clean and the staff very helpful. This place is nothing fancy but comfortable and adequate.

Reviewed on May 15, 2026

Bay Club Resort by Coolvacay

Bay Club Resort by Coolvacay

3 out of 5
Midtown Ocean City
Price was $1,993, price is now $1,582 per person
$1,582
per person
Jul 13 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
8.4/10 Very Good! (39 reviews)
I loved the dock and the gorgeous sunsets .

Reviewed on Sep 7, 2025

Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5
Price was $1,876, price is now $1,500 per person
$1,500
per person
Jul 13 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
9.4/10 Exceptional! (753 reviews)
Clean room, great staff, nice bar

Reviewed on May 13, 2026

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was $1,882, price is now $1,533 per person
$1,533
per person
Aug 5 - Aug 9
found 4 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
9/10 Wonderful! (3,531 reviews)
Nice view of the boardwalk and ocean.

Reviewed on May 16, 2026

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Discover the most popular places to visit in Madison

Harriet Tubman Underground Railroad National Historical Park

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
$262 nightly
The price is $297 total per night from May 26 to May 27
$297 total
May 26 - May 27
Total with taxes and fees
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
$162 nightly
The price is $177 total per night from May 25 to May 26
$177 total
May 25 - May 26
Total with taxes and fees
8.6/10 Excellent! (1,004 reviews)
Air was very comfortable Didn't eat breakfast

Reviewed on May 15, 2026

Rod 'N' Reel Resort
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln St. Michaels MD
$603 nightly
The price is $663 total per night from May 31 to Jun 1
$663 total
May 31 - Jun 1
Total with taxes and fees
9.6/10 Exceptional! (385 reviews)
We had yet another wonderful stay, great views, very comfortable. Some areas (primarily outside) would benefit from some paint.

Reviewed on May 14, 2026

Inn at Perry Cabin
See all 573 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 from $773 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.