Madison-on-the-Lake Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

Top Holiday Package Deals in Madison-on-the-Lake

Price found within the past 48 hours. Click for updated prices.
Hampton Inn Cleveland-Westlake

Hampton Inn Cleveland-Westlake

2.5 out of 5
Price was CA $909, price is now CA $857 per person
CA $857
per person
Jun 10 - Jun 12
found 14 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Cleveland (CLE)
8.2/10 Very Good! (1,000 reviews)
Everything about our stay was excellent! Room was very clean and well appointed. Staff was friendly and helpful. Breakfast was ample and diverse. A truly refreshing stay.

Reviewed on May 9, 2026

Hilton Garden Inn Cleveland Downtown

Hilton Garden Inn Cleveland Downtown

3 out of 5
Downtown Cleveland
Price was CA $1,009, price is now CA $913 per person
CA $913
per person
Jun 10 - Jun 12
found 14 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Cleveland (CLE)
7.6/10 Good! (1,008 reviews)
The location was perfect, only 8min walk from the Arena and Stadium

Reviewed on May 3, 2026

Landing Apartments near Rivergate Park Area

Landing Apartments near Rivergate Park Area

4 out of 5
Cuyahoga Valley
Price was CA $1,037, price is now CA $965 per person
CA $965
per person
Jun 10 - Jun 12
found 14 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Cleveland (CLE)
10/10 Exceptional! (3 reviews)
Hotel Kilbourne Downtown Sandusky

Hotel Kilbourne Downtown Sandusky

2.5 out of 5
Historic Downtown Sandusky
Price was CA $1,044, price is now CA $971 per person
CA $971
per person
Jun 10 - Jun 12
found 14 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Cleveland (CLE)
9/10 Wonderful! (690 reviews)
Everything was first rate

Reviewed on Mar 29, 2026

Hotel Indigo Cleveland Downtown by IHG

Hotel Indigo Cleveland Downtown by IHG

3.5 out of 5
Downtown Cleveland
Price was CA $993, price is now CA $931 per person
CA $931
per person
Jun 10 - Jun 12
found 14 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Cleveland (CLE)
8.4/10 Very Good! (1,656 reviews)
Twyla in the restaurant and Beth at the front desk are awesome employees. I wouldn’t stay anywhere else

Reviewed on May 6, 2026

Where to stay in Madison-on-the-Lake

Find the best Madison-on-the-Lake areas and neighborhoods for the activities you enjoy most. Learn more about Madison-on-the-Lake
Default Image

George Haywood's Lakefront

Though George Haywood's Lakefront might not have many top sights, you can venture to the surrounding area to see attractions like Rabbit Run Community Arts Association and beach near Cumings Beach Park.

Find hotels in George Haywood's Lakefront

Madison-on-the-Lake Hotel Deals

Madison on the Lake Home with Lake Erie views & Pool in Wine Country!

Madison on the Lake Home with Lake Erie views & Pool in Wine Country!

Madison OH
9.6/10 Exceptional! (27 reviews)
Spent a week and enjoyed my time here. The house is lovely and has all the things needed to be comfortable. Nice area & very quiet. Would return again. Host responded quickly to my questions.

Reviewed on Feb 14, 2026

Get rates
Madison on the Lake Home with Lake Erie views & Pool in Wine Country!
Lakefront Property, Family Friendly and Pets Allowed

Lakefront Property, Family Friendly and Pets Allowed

Madison OH
9.8/10 Exceptional! (120 reviews)
Stayed for several days around New Year’s with a group of family and friends. Warm and cozy home kept us safe from the snowfall coming down and provided beautiful views of the lake! Communication with host was excellent, even went out of their way to help us to successfully operate the hot tub (which ...

Reviewed on Jan 3, 2026

Get rates
Lakefront Property, Family Friendly and Pets Allowed
Red Roof Inn Cleveland - Mentor/ Willoughby

Red Roof Inn Cleveland - Mentor/ Willoughby

2 out of 5
4166 State Route 306 Willoughby OH
Fully refundableReserve now, pay when you stay
The price is CA $87 per night from May 17 to May 18
CA $87
CA $100 total
May 17 - May 18
includes taxes & fees
7.4/10 Good! (1,004 reviews)
BED BUGS! BED BUGS! BED BUGS!

Reviewed on May 5, 2026

Red Roof Inn Cleveland - Mentor/ Willoughby
See all 647 properties in Madison-on-the-Lake
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

Frequently asked questions

How much does a Madison-on-the-Lake vacation package cost?
Live it up in Madison-on-the-Lake from as low as CA $857. We offer a great selection of flights, hotels and rental cars to suit every budget and style. Score even more discounts when you add a few tours or experiences to your vacation package.
How do I get a cheap travel package to Madison-on-the-Lake?
Bundle your hotel and flight bookings, toss in extras such as a rental car or activities, and save with a Madison-on-the-Lake vacation package. You won't just land exciting discounts on your adventure — you'll have a world of choice at your fingertips too. When you book with Expedia, you can choose from more than 550 partner airlines and 1,000,000 properties all over the world. Your dream vacation begins right here, right now!
How far in advance should I book my Madison-on-the-Lake vacation?
Savvy travelers book early. Air carriers generally release flights up to a year prior to departure, and this is when you can score some rock-bottom prices. Boss just told you to take some vacation time in a few weeks? No problem! Expedia are never short on fantastic bargains to send you on the getaway of your dreams, at an affordable price.
What does an Expedia Madison-on-the-Lake travel package include?
Expedia has everything you need to organize your Madison-on-the-Lake trip, but what your package looks like is your call. Choose from any combination of rental cars, flights and hotels. Chasing a few activities to keep you on the move? Once you've made your booking, you can add them too. Whatever your style, there's a vacation package to suit your needs.
Can I choose my airline with a Madison-on-the-Lake Expedia vacation package?
You can, and with over 550 airlines to pick from worldwide, you've got lots of choice. Take a look at the available options and see which airline best fits your budget and needs.
If I'm not able to travel, can I cancel my Madison-on-the-Lake vacation package?
If your travel plans in Madison-on-the-Lake have been upended, it's a relief to know that it is possible to cancel your booking. If your booking was made in the last 24 hours, you may be able to receive a refund. If your booking was made more than 24 hours ago, your airline, hotel or car rental company may impose a fee. For more information, visit our Customer Service Portal.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.