Madison Vacation Packages

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Your Madison Vacation

The easiest way to experience this exciting city is with a custom-made Madison vacation package. Base yourself in the neighborhood of Downtown Cambridge, which is good for bars and pubs, culture and cafes or go someplace else — our packages are all about you. There's plenty to put on your must-see list during a trip to Madison, beginning with leading attractions such as Harriet Tubman Underground Railroad National Historical Park and Spocott Windmill. Whatever your travel plans or budget, organizing your ultimate tailored Madison vacation is easy with Expedia.

Top Madison Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was CA $1,418, price is now CA $1,251 per person
CA $1,251
per person
Dec 27 - Jan 1
just found
Roundtrip non-stop flight included
Montreal (YUL) to Salisbury (SBY)
9/10 Wonderful! (3,946 reviews)
It was a good stay.

Reviewed on Oct 26, 2026

Beach Walk

Beach Walk

2 out of 5
Downtown Ocean City
Save 100% on your flight
Price was CA $4,720, price is now CA $3,326 per person
CA $3,326
per person
Dec 27 - Jan 1
just found
Roundtrip non-stop flight included
Montreal (YUL) to Salisbury (SBY)
7.6/10 Good! (126 reviews)
We never slept here. The room was incredibly dirty. Stained sheets, stained carpet, god only knows what on the walls in the bathroom. The table and chairs were a table that folded out from the wall with a stick underneath. The chairs were two rusty folding chairs. The blinds in the window were busted up and only covered half the window. I honestly don’t know how they’ve not been shut down. We quickly found another hotel.

Reviewed on Oct 13, 2026

Miramar Condominiums

Miramar Condominiums

2 out of 5
Downtown Ocean City
Price was CA $2,149, price is now CA $1,875 per person
CA $1,875
per person
Dec 27 - Jan 1
just found
Roundtrip non-stop flight included
Montreal (YUL) to Salisbury (SBY)
9.4/10 Exceptional! (34 reviews)

Bethany Beach Ocean Suites Residence Inn by Marriott

Bethany Beach Ocean Suites Residence Inn by Marriott

3 out of 5
Downtown Bethany Beach
Price was CA $1,790, price is now CA $1,597 per person
CA $1,597
per person
Dec 27 - Jan 1
just found
Roundtrip non-stop flight included
Montreal (YUL) to Salisbury (SBY)
9/10 Wonderful! (873 reviews)
Our experience as a whole was excellent. The hotel is beautiful and location is excellent. The hotel restaurant was excellent. Very delicious crab cake! That being said, the hotel is starting to show wear. Our bathroom door was warped from water damage. The sink was clogged. The bathroom mirror lighting needed replaced. I did call the front desk and maintenance came right away. The sink was fixed. They could not fix the lighting as they did not have the parts. The main part of our suite had cobwebs. I know it’s off season, but I would think this is the time to have the property maintenance done before the busy season starts. It’s a great hotel and I will go back.

Reviewed on Oct 26, 2026

Ready to book your vacation to Madison?

 

Choose your dates

Madison Hotel Deals

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 CA $184 per night from Nov 17 to Nov 18
CA $184
CA $205 total
Nov 17 - Nov 18
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
"I hadn't been here in many years, and was pleasantly surprised at all the upgrades that have been made! Truly a luxurious stay and amenities"

Reviewed on Oct 26, 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 CA $108 per night from Nov 26 to Nov 27
CA $108
CA $118 total
Nov 26 - Nov 27
includes taxes & fees
8/10 Very good! (1,012 reviews)
"Especially given the price, a disappointing experience. First among the issues were paper thin walls, where we could clearly hear the conversations in neighboring rooms. In addition a lot of signs of deferred maintenance or repairs using low cost/low quality options."

Reviewed on Oct 26, 2026

St Michaels Inn
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 CA $202 per night from Nov 23 to Nov 24
CA $202
CA $269 total
Nov 23 - Nov 24
includes taxes & fees
8.8/10 Excellent! (1,009 reviews)
"Everything was awesome"

Reviewed on Oct 26, 2026

Hyatt Regency Chesapeake Bay
See all 569 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular Madison attractions

Harriet Tubman Underground Railroad National Historical Park

9.6/10 (95 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.
See properties

Frequently asked questions

How much does a Madison vacation package cost?
You can pick up a vacation package to this top destination from CA $1,251 on Expedia. However, how much your vacation to Madison costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Madison?
January, February and November are the best times to search for cheap Madison vacation packages. Opting to travel in quieter periods means you can generally find better prices on accommodations and flights.
How many days is enough for Madison?
Generally, a handful of days is enough to go to the top attractions during your Madison vacation. But if you prefer to have time to kick back or take day tours, consider extending your itinerary.
How to find the best Madison package deals?
Begin your search for a Madison package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Madison package deal right away, just switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Madison getaway off to a flying start.
Is it cheaper to book a Madison vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking accommodations and flights individually. Better still, you can personalize your Madison trip to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Madison?
If you have your Madison vacation dates confirmed, book as soon as you can to grab some awesome deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for impromptu escapes.
How to plan a trip to Madison?

  1. Choose your dates: The things you plan to do in Madison and your favourite season will help you decide when to go.
  2. Figure out your budget: Make sure you have enough money to pay for everything from meals and transportation to flights and activities. Your hotel will likely be the largest expense during your trip to Madison.
  3. Decide how long to go away for: Now that you know more about Madison, you can figure out the perfect length of your break. Pull together a rough plan and give yourself enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, flights, car rental and more into a tailored Madison vacation package.

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