Madison Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to SAR 390 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

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 SAR 747 per night from May 6 to May 7
SAR 747
SAR 1,027 total
includes taxes & fees
6 May - 7 May
8.6/10 Excellent! (1,002 reviews)
"Great spot."

Reviewed on 8 April 2025

Hyatt Regency Chesapeake Bay
Inn at Perry Cabin
Inn at Perry Cabin
5 out of 5
308 Watkins Ln, St. Michaels, MD
The price is SAR 1,807 per night from May 11 to May 12
SAR 1,807
SAR 2,186 total
includes taxes & fees
11 May - 12 May
9.4/10 Exceptional! (340 reviews)
"Our stay here was excellent. The highlight was arguably the check-in, where we were surprised with a birthday welcome, as well as a little onesie for our soon to arrive baby girl. This was a birthday/baby moon trip and we shared this info prior to arrival, and the staff was incredible in providing ..."

Reviewed on 5 April 2025

Inn at Perry Cabin
St Michaels Inn
St Michaels Inn
2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
Fully refundableReserve now, pay when you stay
The price is SAR 453 per night from May 5 to May 6
SAR 453
SAR 498 total
includes taxes & fees
5 May - 6 May
8/10 Very Good! (1,002 reviews)
"Worthwhile"

Reviewed on 16 April 2025

St Michaels Inn
See all 498 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 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.

Discover the most popular places to visit in Madison

Cambridge

Harriet Tubman Underground Railroad National Historical Park

4.5/5(14 reviews)

You can spend time studying the exhibits at Harriet Tubman Underground Railroad National Historical Park in Madison. While you're in the area, stroll along the riverfront.

Harriet Tubman Underground Railroad National Historical Park