Madison Holidays

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    Better together

    Save up to NZ$616 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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    Plan, book, and manage your trip all in one place

Madison Holiday

Our pick of the best 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 NZ$486 per night from 25 Aug to 26 Aug
NZ$486
25 Aug - 26 Aug
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
"Great stay at the Hyatt! Beautiful location and property, staff incredible! Only lost a star because drinks/food a bit overpriced and not 5 star."

Reviewed on 18 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 NZ$237 per night from 3 Sept to 4 Sept
NZ$237
3 Sept - 4 Sept
includes taxes & fees
7.8/10 Good! (876 reviews)
Amazing service and staff!
"Super comfortable bed! Haven’t sleep that well in a hotel for a while! The service and friendliness from all staff was AMAZING! Everyone was so kind. Our kids loved the pool as well. Wish we had a longer stay."

Reviewed on 18 Aug. 2025

Solomons Inn Resort & Marina
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln, St. Michaels, MD
The price is NZ$1,179 per night from 22 Sept to 23 Sept
NZ$1,179
22 Sept - 23 Sept
includes taxes & fees
9.4/10 Exceptional! (359 reviews)
"IPC is a "hidden gem." It was great, from "soup to nuts." Especially the staff, who were all friendly, polite, knowledgeable, flexible, and helpful. Thanks to all of them on our behalf, please: staff are what make all the difference at any resort. (SPA treatments are a must.) Just one suggestion: ..."

Reviewed on 14 Aug. 2025

Inn at Perry Cabin
See all 519 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.