Madison Vacation Packages

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Your Madison Vacation

Say goodbye to planning worries and hello to a Madison vacation package. With the finer details organized before you take off, you can focus on discovering the best of this city, starting with Fairport Harbor, which is good for watersports, views and nature. If your trip to Madison includes a little sightseeing, hit up much-loved attractions like Chalet Debonne Vineyards, Grand River Cellars Winery and Laurentia Vineyard & Winery. Don't delay visiting this destination any longer. The perfect Madison vacation is just a few clicks away with Expedia.

Top Madison Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Cedar Stables Inn and Suites

Cedar Stables Inn and Suites

2.5 out of 5
Price was CA $1,225, price is now CA $1,016 per person
CA $1,016
per person
Sep 11 - Sep 14
found 1 hour ago
Roundtrip flight included
Toronto (YYZ) to Cleveland (CLE)
8.8/10 Excellent! (526 reviews)
Checking in wasn't too bad once we figured out where to go. The shower stopped up the first night so I called the front desk and was told 'I will let maintenance know" We never saw them or heard from them. So the next morning, I let housekeeping know about it being stopped up again and was told again....I will let maintenance know. Still nothing from anyone. I wasnt even able to take a shower because it was not draining at all. After being at Cedar Point all day, you really need to be able to shower.

Reviewed on Jul 6, 2026

The Inn at Fulton

The Inn at Fulton

2 out of 5
Price was CA $1,364, price is now CA $1,125 per person
CA $1,125
per person
Sep 11 - Sep 14
found 1 hour ago
Roundtrip flight included
Toronto (YYZ) to Cleveland (CLE)
8.2/10 Very good! (37 reviews)
We would absolutely stay here again. It was a great location close to great restaurant options and pretty views of the downtown and water. In the reviews I read the biggest complaint was the noise level. You could clear as day hear any conversations of other rooms if you were in the hallway. Once inside our rooms it wasn’t as bad but we are pretty easy sleepers and other guests were very respectful.

Reviewed on Mar 21, 2026

Hotel Kilbourne Downtown Sandusky

Hotel Kilbourne Downtown Sandusky

2.5 out of 5
Historic Downtown Sandusky
Price was CA $1,510, price is now CA $1,250 per person
CA $1,250
per person
Sep 11 - Sep 14
found 1 hour ago
Roundtrip flight included
Toronto (YYZ) to Cleveland (CLE)
9/10 Wonderful! (708 reviews)
Great vibes, conveniently located, good food and drinks options

Reviewed on Jul 9, 2026

The Westin Cleveland Downtown

The Westin Cleveland Downtown

4 out of 5
Downtown Cleveland
Price was CA $2,023, price is now CA $1,694 per person
CA $1,694
per person
Sep 18 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Cleveland (CLE)
8.8/10 Excellent! (2,253 reviews)
The staff was friendly and helpful. The room was clean and fresh!

Reviewed on Jul 10, 2026

Quality Lodge

Quality Lodge

2.5 out of 5
Price was CA $1,209, price is now CA $1,017 per person
CA $1,017
per person
Sep 11 - Sep 14
found 1 hour ago
Roundtrip flight included
Toronto (YYZ) to Cleveland (CLE)
7.8/10 Good! (347 reviews)
This area is nothing like the pictures, just was not what we were expecting.

Reviewed on Jun 14, 2026

Where to stay in Madison

Find the best Madison areas and neighborhoods for the activities you enjoy most. Learn more about Madison
A sunset over the ocean with clouds reflecting the sun's light.

Madison-on-the-Lake

2 out of top 10 points of interest in this area

While visiting Madison-on-the-Lake, you might make a stop by sights like Lake Erie and Rabbit Run Community Arts Association.

Find hotels in Madison-on-the-Lake

Ready to book your vacation to Madison?

 

Choose your dates

Madison Hotel Deals

Hampton Inn Madison

Hampton Inn Madison

2.5 out of 5
171 Water Tower Drive Madison OH
Fully refundableReserve now, pay when you stay
The price is CA $185 per night from Jul 19 to Jul 20
CA $185
CA $213 total
Jul 19 - Jul 20
includes taxes & fees
Hampton Inn Madison
Holiday Inn Express & Suites Madison by IHG

Holiday Inn Express & Suites Madison by IHG

2.5 out of 5
181 WATER TOWER DRIVE Madison OH
Fully refundable
The price is CA $156 per night from Jul 30 to Jul 31
CA $156
CA $180 total
Jul 30 - Jul 31
includes taxes & fees
9.4/10 Exceptional! (736 reviews)
"We stayed at this location because of the wineries nearby. Both the hotel website and the Debonne winery website advertised free shuttles to and from the winery. The website was clear that the shuttles were daily and complimentary. When we got there we were told first that there weren’t shuttles, ..."

Reviewed on Jul 7, 2026

Holiday Inn Express & Suites Madison by IHG
Charming 2-bedroom house in delightful Madison with AC

Charming 2-bedroom house in delightful Madison with AC

Madison OH
The price is CA $383 per night from Jul 21 to Jul 22
CA $383
CA $453 total
Jul 21 - Jul 22
includes taxes & fees
8/10 Very good! (1 review)
"Homey with a short drive to beach acess and a nice winery. Owner helpful"

Reviewed on Jul 6, 2026

Charming 2-bedroom house in delightful Madison with AC
See all 684 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
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Stay near popular Madison attractions

Hogback Ridge

9.6/10 (5 reviews)
Explore the great outdoors at Hogback Ridge, a lovely green space in Madison. Take in the theater scene while you're in the area.
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 $1,016 on Expedia. But how much your vacation to Madison costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Madison?
You can typically find reduced prices and better availability in February, April and November. Check out our cheap Madison vacation packages and you could get some great off-season deals.
How many days is enough for Madison?
Generally, a handful of days is enough to go to the major sights during your Madison vacation. However, if you want to have more time to rest or go on day tours, think about extending your itinerary.
How to find the best Madison package deals?
Finding a cheap Madison package deal is a cinch with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your budget, apply some filters and browse what's available. You can customize your search by "Amenities," "Property type," "Traveller experience" and more. Order the results by "Price: low to high" to view the most affordable Madison package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Madison vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and hotels separately. Better still, you can customize your Madison escape to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Madison?
If you've got your Madison vacation dates locked in, book as early as you can to bag some unbeatable deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for impromptu escapes.
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. Plan your budget wisely: In addition to the cost of your hotel, you should factor in other expenses. These include flights, transportation and food. Also, set aside some extra funds for unexpected expenses that may come up during your trip to Madison.
  3. Decide your trip length: Think about how much time you want to spend discovering Madison. Plan your days so you can get to all the activities and attractions you're interested in at a leisurely pace.
  4. Combine your airfare and accommodations: After you've nailed down your dates and duration, book the perfect Madison vacation package for you.

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