Madison Vacations from $446
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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.
The Latest Madison vacation packages
Price found within the past 48 hours. Click for updated prices.
Kimpton Schofield Hotel by IHG
Downtown Cleveland
$446
per person
Dec 5 - Dec 7
found 12 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Cleveland (CLE)
9/10 Wonderful! (1,020 reviews)
The property was in excellent shape, My 2 complaints were that the mattress was certainly due for replacement and not the same quality as a Marriott or Westin, and for the price of a room, and all of the nice amenities, they cheaped out on cheap single ply toilet paper. The Betts restaurant was exceptionally busy because of the multiple events going on that night, but the service was excellent, the food was unbelievably good and the food and drink prices were shockingly inexpensive. The next time I am in town for an event or even for a weekend getaway I would certainly return.
Reviewed on Sep 21, 2026
Landing Apartments near Rivergate Park Area
Cuyahoga Valley
$782
per person
Dec 14 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Cleveland (CLE)
9/10 Wonderful! (10 reviews)
Clean and brand new pet friendly apartment in a safe neighborhood. Also has a nice pool.
Reviewed on Sep 8, 2026
Holiday Inn Express Mentor Banquet Center by IHG
$641
per person
Dec 14 - Dec 19
found 13 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Cleveland (CLE)
8.4/10 Very Good! (483 reviews)
The only real issue we had was the elevator. We got stuck for a very brief time. We went to the desk and she told us they knew it wasn’t working properly. Probably should have had a sign to let people know. Otherwise, the hotel was fine!
Reviewed on Sep 21, 2026
ROOST Cleveland
Downtown Cleveland
$482
per person
Dec 5 - Dec 7
found 12 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Cleveland (CLE)
9.6/10 Exceptional! (814 reviews)
The desk staff were so attentive! The apartment was a really cool change of pace from typical hotel room. Great location for baseball and basketball games
Reviewed on Sep 22, 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
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.
George Haywood's Lakefront
If you're spending some time in George Haywood's Lakefront, Lake Erie is a top sight worth visiting.
Cumings Beach Park
Though Cumings Beach Park might not have many top sights, you can venture to the surrounding area to see attractions like Geneva State Park and Geneva Marina.
Madison - Lakeland
While Madison - Lakeland might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Geneva State Park and Geneva Marina.
Madison Beach
Though Madison Beach might not have many top sights, you can venture to the surrounding area to see attractions like Geneva State Park and Geneva Marina.
Stay near popular Madison attractions
Hogback Ridge
9.6/10 (5 reviews)
Hike the unique hogback formation where steep valleys flank a narrow ridge resembling a hog's spine. Explore diverse habitats via accessible boardwalks and scenic overlook decks amid seasonal wildflower displays.
Laurentia Vineyard & Winery
9.0/10 (17 reviews)
This Grand River Valley estate winery welcomes guests with a log-and-stone tasting room featuring a central fireplace. Sample their acclaimed wines while enjoying seasonal dishes on the patio overlooking the vineyards.
Grand River Cellars Winery
9.0/10 (23 reviews)
This award-winning Ohio winery showcases local Grand River Valley grapes in a rustic setting. Sample diverse wine flights on their woodland patio while enjoying live music and locally-inspired cuisine.
Chalet Debonne Vineyards
9.2/10 (44 reviews)
Debonné Vineyards, Ohio's largest estate winery, offers over 50 wines across 175 acres in the Grand River Valley. Sample wine flights in the rustic chalet while enjoying live entertainment on weekends.
Baci Winery
Savor estate-grown wines and Italian cuisine at Baci Winery, a Grand River Valley gem with vineyard panoramas. Weekend visitors can enhance their tasting experience with live music performances on the scenic grounds.
Rabbit Run Community Arts Association
10.0/10 (1 review)
One of the few remaining barn theaters in the US, Rabbit Run offers intimate performances in a 19th-century setting. Bring a picnic dinner to enjoy on the landscaped grounds before summer evening shows.
Madison Hotel Deals
Hampton Inn Madison
171 Water Tower Drive Madison OH
Fully refundableReserve now, pay when you stay
$106 nightly
$122 total
Oct 11 - Oct 12
Total with taxes and fees
Holiday Inn Express & Suites Madison by IHG
181 WATER TOWER DRIVE Madison OH
Fully refundable
$97 nightly
$112 total
Sep 28 - Sep 29
Total with taxes and fees
Lakefront Retreat w/ Private Beach. Sleeps 12
Madison OH
9.8/10 Exceptional! (129 reviews)
"Property and location are excellent—- that’s why we keep coming back year after year"
Reviewed on Aug 24, 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.
Find the Best Madison Vacation Packages
Madison Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 3,200 |
Max Temp Winter | 35ºF |
Max Temp Summer | 75ºF |
Top Sights | Chalet Debonne Vineyards, Laurentia Vineyard & Winery and Grand River Cellars Winery |
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Frequently asked questions
How much does a Madison vacation package cost?
Offering excellent value package deals from $446 on Expedia, you'll be thrilled with how little a vacation to Madison costs! Expedia's packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Madison?
If you'd like to snag a cheap Madison vacation package, consider traveling in February, November and December. You'll usually find better rates on hotels and flights during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Madison?
The ideal length for your Madison vacation depends on what you'd like to see. Usually, a few days to a week will give you enough time to check out all the leading attractions and discover some hidden treasures along the way.
How to find the best Madison package deals?
Finding a cheap Madison package deal is easy with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, add a few filters and see what's available. You can personalize your search by "Amenities," "Property type," "Traveler experience" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Madison package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are generally lower.
Is it cheaper to book a Madison vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll generally snag a better deal than booking each component separately. And you'll still enjoy the flexibility to create a personalized Madison vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Madison?
Enjoy fantastic discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for a spur-of-the-moment Madison escape.
Does Expedia offer Book Now, Pay Later Madison vacation packages?
Your Madison trip is meant to be an escape from your daily routine, not a source of money-related stress. So to allow you a bit more flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.
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- Walnut Beach Park
- Mentor Marsh - Carol H. Sweet Nature Center
- Austinburg Township Park
- Rabbit Run Community Arts Association
- Ashtabula Vacations
- Pioneer Waterland & Dry Fun Park
- Deer Lake Golf Club
- M Cellars
- South River Vineyard
- North Coast Marina
- Ashtabula Recreation Unlimited Marina
- Visit Geneva-on-the-Lake
- Geneva Vacations
- Fairport Harbor Lakefront Park Beach
- Old Firehouse Winery
- Saybrook Township Park
- Geneva State Park
- Black Brook Golf Course
- Mechanicsville Road Covered Bridge
- Allison's Mini-Golf
- Lakehouse Inn & Winery
- Headlands Beach State Park
- Chalet Debonne Vineyards
- Harpersfield Covered Bridge
- Geneva-On-The-Lake Vacations
- Fairport Harbor Marine Museum and Lighthouse
- Visit Madison
- Painesville Vacations
- Visit Geneva
- Laurentia Vineyard & Winery
- Adventure Zone
- Little Mountain Country Club
- Ferrante Winery
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
