Madison Holidays

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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$544 per night from 5 Aug to 6 Aug
S$544
5 Aug - 6 Aug
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
"Only thing was for older and senior people the toilet was to low the the floor, they need to be higher."

Reviewed on 4 Jul, 2026

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
The price is S$263 per night from 8 Jul to 9 Jul
S$263
8 Jul - 9 Jul
includes taxes & fees
8.6/10 Excellent! (1,008 reviews)
"Clean room, good shower, comfortable bed. Amenities were severely lacking. Casino was a joke, and not many other things to do other than eat and drink. No real beach or place to sit by the water, just the dock. Overpriced drinks and food. Surrounding area is not visitor friendly. Might as well own ..."

Reviewed on 5 Jul, 2026

Rod 'N' Reel Resort
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 S$137 per night from 5 Aug to 6 Aug
S$137
5 Aug - 6 Aug
includes taxes & fees
8.2/10 Very good! (1,005 reviews)
"The inn is quant and a little dated, but the rooms are clean and comfortable. Depending on which room you are assigned, the parking is right outside the door. All the staff were very friendly and helpful. The breakfast area is very nice and the breakfast selections are good. It is close to town but ..."

Reviewed on 5 Jul, 2026

St Michaels Inn
See all 575 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.

Stay near popular Madison attractions

Harriet Tubman Underground Railroad National Historical Park

9.6/10 (95 reviews)
You can spend an afternoon browsing the exhibits at Harriet Tubman Underground Railroad National Historical Park during your travels in Madison. While you're in the area, stroll along the riverfront.
See properties

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.

Explore a world of travel with Expedia

* 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.