Madison Vacations

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    Better together

    Save up to ₩234,741 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Find the Best Madison Vacation Packages

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
The price is ₩287,776 per night from Aug 25 to Aug 26
₩287,776
₩392,875 total
Aug 25 - Aug 26
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
A Gem by the Bay
"Facility is magnificent; very family and child-oriented; good programming for children."

Reviewed on Aug 11, 2025

Hyatt Regency Chesapeake Bay
Solomons Inn Resort & Marina

Solomons Inn Resort & Marina

2.5 out of 5
155 Holiday Dr. P.O. Box 1099, Solomons, MD
Fully refundableReserve now, pay when you stay
The price is ₩198,749 per night from Sep 1 to Sep 2
₩198,749
₩220,624 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (867 reviews)
"The hotel was newly renovated and the rooms were very nice and beds very comfortable. The pool was amazing and the staff was very friendly and helpful. Will be back."

Reviewed on Aug 12, 2025

Solomons Inn Resort & Marina
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
Fully refundable
The price is ₩139,694 per night from Sep 1 to Sep 2
₩139,694
₩153,666 total
Sep 1 - Sep 2
includes taxes & fees
8/10 Very Good! (1,001 reviews)
"Very nice stay"

Reviewed on Aug 13, 2025

St Michaels Inn
See all 510 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.

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?
January, February and November are great times to look for cheap Madison vacation packages. Traveling in quieter periods means you can generally find lower prices on accommodations and flights.
How many days is enough for Madison?
With a well-organized itinerary, you can easily visit the main Madison sights in a handful of days. But if you'd like to discover hidden spots or take day trips, think about booking your Madison vacation for longer.
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.
How to plan a trip to Madison?

  1. Choose the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to travel to Madison.
  2. Set your budget: Factor in costs such as food, flights and transportation when working out how much to put aside for your trip to Madison. Then, pick a hotel that fits your budget, whether that's an affordable stay or a more upscale getaway.
  3. Decide your trip length: Consider how long you'd like to spend exploring Madison. Plan your days so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to choose a Madison vacation package that brings all your bookings together.

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