Madison Vacations from $188

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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.
Towneplace Suites By Marriott Cleveland Westlake

Towneplace Suites By Marriott Cleveland Westlake

3 out of 5
Save 100% on your flight
Price was $256, price is now $188 per person
$188
per person
Jan 16 - Jan 19
found 13 hours ago
Roundtrip flight included
Boston (BOS) to Cleveland (CLE)
15.6/10 Exceptional! (454 reviews)
convenient and good value

Reviewed on Oct 16, 2025

Fidelity Hotel

Fidelity Hotel

4 out of 5
Downtown Cleveland
Save 100% on your flight
Price was $495, price is now $327 per person
$327
per person
Feb 6 - Feb 9
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Cleveland (CLE)
19.2/10 Exceptional! (471 reviews)
Loved everything about this place. Staff, vibe and location were all wonderful. Would definitely stay again!

Reviewed on Nov 18, 2025

Hampton Inn & Suites Cleveland/Independence

Hampton Inn & Suites Cleveland/Independence

2.5 out of 5
Price was $366, price is now $258 per person
$258
per person
Feb 6 - Feb 9
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Cleveland (CLE)
17.6/10 Exceptional! (1,001 reviews)
It was clean and staff were nice. One suggestion in handicap accessible rooms toilets should be handicap as well. They were too low with nothing to hold on to when lowering yourself.

Reviewed on Nov 15, 2025

Hilton Garden Inn Cleveland Downtown

Hilton Garden Inn Cleveland Downtown

3 out of 5
Downtown Cleveland
Price was $384, price is now $275 per person
$275
per person
Feb 6 - Feb 9
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Cleveland (CLE)
14.8/10 Exceptional! (1,004 reviews)
Natalie was great ! Shes the best

Reviewed on Nov 18, 2025

Hotel Indigo Cleveland Downtown by IHG

Hotel Indigo Cleveland Downtown by IHG

3.5 out of 5
Downtown Cleveland
Price was $379, price is now $272 per person
$272
per person
Feb 6 - Feb 9
found 5 hours ago
Roundtrip flight included
Boston (BOS) to Cleveland (CLE)
16.8/10 Exceptional! (1,442 reviews)
Everything was awesome and clean. Short walk to Rocket Arena. Nice atmosphere and good bar foods. The only thing that was a issue was, they lost my keys at Valet parking.

Reviewed on Nov 17, 2025

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Where to stay in Madison

Find the best Madison areas and neighborhoods for the activities you enjoy most. Learn more about Madison
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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.

Find hotels in Madison-on-the-Lake

Discover the most popular places to visit in Madison

Laurentia Vineyard & Winery

You can enjoy a tasting or tour at Laurentia Vineyard & Winery during your travels to Madison. Take in the theater scene while you're in the area.

Laurentia Vineyard & Winery

Grand River Cellars Winery

You can enjoy a tasting or tour at Grand River Cellars Winery during your travels to Madison. Wander the lakeside in this relaxing area.

Grand River Cellars Winery

Chalet Debonne Vineyards

4.5/5(6 reviews)

You can enjoy a tasting or tour at Chalet Debonne Vineyards during your travels to Madison. Wander the lakeside in this trendy area.

Chalet Debonne Vineyards

Madison Hotel Deals

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
$82 nightly
The price is $95 total per night from Dec 14 to Dec 15
$95 total
Dec 14 - Dec 15
Total with taxes and fees
9.2/10 Wonderful! (657 reviews)
The staff was professional and check in was completed under two minutes. The room is spacious and extremely clean.

Reviewed on Nov 3, 2025

Holiday Inn Express & Suites Madison by IHG
Hampton Inn Madison

Hampton Inn Madison

2.5 out of 5
171 Water Tower Drive Madison OH
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $108 total per night from Nov 30 to Dec 1
$108 total
Nov 30 - Dec 1
Total with taxes and fees
9.6/10 Exceptional! (766 reviews)
Breakfast was good, room was clean and comfortable.

Reviewed on Nov 9, 2025

Hampton Inn Madison
The Caboose

The Caboose

Madison OH
9.6/10 Exceptional! (5 reviews)
The Caboose is adorable. It was a fun and unique getaway for our anniversary. Host was very accommodating. The nature trails were an unexpected treat as were the goats.

Reviewed on Sep 21, 2025

Get rates
The Caboose
See all 674 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.

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 $188 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.