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.
Hilton Garden Inn Cleveland Downtown
Downtown Cleveland
Price was CA $1,304, price is now CA $1,052 per person
CA $1,052
per person
May 18 - May 22
found 17 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Cleveland (CLE)
7.6/10 Good! (1,008 reviews)
For baseball fan, this is the perfect place to stay. Good price. Walkable thru all Cleveland.
Reviewed on Apr 8, 2026
The Westin Cleveland Downtown
Downtown Cleveland
Price was CA $2,080, price is now CA $1,651 per person
CA $1,651
per person
May 18 - May 22
found 17 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Cleveland (CLE)
8.6/10 Excellent! (2,104 reviews)
Yes, diffently a place i will return to on my next overnight stay in Cleveland. Staff was AWESOME, very polite and helpful with questions and directions. I mean everybody, from the valet people, housekeeping to registration. Absolutely no issues. Thanks job well done.
Reviewed on Apr 7, 2026
Kimpton Schofield Hotel by IHG
Downtown Cleveland
Price was CA $1,508, price is now CA $1,225 per person
CA $1,225
per person
May 18 - May 22
found 17 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Cleveland (CLE)
8.8/10 Excellent! (1,001 reviews)
The staff was very welcoming and helpful.
Reviewed on Apr 4, 2026
Holiday Inn Cleveland Clinic by IHG
Fairfax
Price was CA $1,363, price is now CA $1,141 per person
CA $1,141
per person
May 18 - May 22
found 17 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Cleveland (CLE)
8.8/10 Excellent! (1,305 reviews)
Outstanding property convenient to Cleveland Clinic. Will stay here again.
Reviewed on Apr 7, 2026
Hilton Cleveland Downtown
Downtown Cleveland
Price was CA $2,019, price is now CA $1,704 per person
CA $1,704
per person
May 18 - May 22
found 17 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Cleveland (CLE)
9.2/10 Wonderful! (1,355 reviews)
Nice hotel, the room was clean enough. We had the breakfast buffet, which was pretty good. The staff at the Noshery was phenomenal, front desk staff was awesome too. I would definitely stay here again.
Reviewed on Apr 4, 2026
Where to stay in Madison
Find the best Madison areas and neighborhoods for the activities you enjoy most. Learn more about Madison
Madison-on-the-Lake
1 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.
Madison Hotel Deals
Hampton Inn Madison
171 Water Tower Drive Madison OH
Fully refundableReserve now, pay when you stay
The price is CA $141 per night from Apr 16 to Apr 17
CA $141
CA $162 total
Apr 16 - Apr 17
includes taxes & fees
9.6/10 Exceptional! (803 reviews)
Front desk staff was knowledgeable and helpful. Super clean rooms, fantastic breakfast
Reviewed on Apr 7, 2026
Holiday Inn Express & Suites Madison by IHG
181 WATER TOWER DRIVE Madison OH
The price is CA $134 per night from Apr 16 to Apr 17
CA $134
CA $155 total
Apr 16 - Apr 17
includes taxes & fees
9.4/10 Exceptional! (702 reviews)
Had to leave before 7 so didn’t get to try breakfast. The ice machine on the 3 rd floor was out of order which was an inconvenience. overall it was ok. for the price I had to pay for one night I expected more. It appeared the rates were really inflated for the night I stayed.
Reviewed on Mar 30, 2026
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
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.
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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.
