Madison Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Madison

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 S$364 per night from 25 Aug to 26 Aug
S$364
25 Aug - 26 Aug
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
"Amazing experience! This was our third visit here and it’s just the best spot with the best views—we will keep coming back. The staff could not be more warm and welcoming—everyone is so friendly and helpful. Rooms are super clean and comfortable. Good food and drinks if you don’t want to leave the ..."

Reviewed on 4 Aug, 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 S$204 per night from 1 Sept to 2 Sept
S$204
1 Sept - 2 Sept
includes taxes & fees
7.8/10 Good! (855 reviews)
"The inn is pretty and not far from the boardwalk area in Solomons Island. It was quiet and had few guests during the midweek. The continental breakfast was good and the staff is friendly and helpful. But a few issues were odd: they had to hunt up a remote for our TV and the phone in our room lit ..."

Reviewed on 7 Aug, 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 S$137 per night from 1 Sept to 2 Sept
S$137
1 Sept - 2 Sept
includes taxes & fees
8/10 Very Good! (1,002 reviews)
"Wonderful greeting and assistance from front desk. Quiet room and considerate and welcoming staff. Breakfast is provided as a courtesy and was mainly fruit (orange and apples) yogurt, french toast and powdered eggs. Coffee and juice. Just enough to get your day going. We felt safe and comfortable. ..."

Reviewed on 7 Aug, 2025

St Michaels Inn
See all 517 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 holiday package cost?
You can pick up a holiday package to this popular destination on Expedia. But how much your holiday 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 holiday packages. Travelling in quieter periods means you can generally find lower prices on accommodation and flights.
How many days is enough for Madison?
With a well-organised 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 holiday 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 holiday package as soon as possible.
Is it cheaper to book a Madison holiday as a package?
Expedia holiday 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 holiday by choosing your favourite type of stay, airline and car class.
When to book a holiday 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 holiday 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.