Madison Vacations from $864

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The Latest Madison vacation packages

Price found within the past 48 hours. Click for updated prices.
Lantern Motel

Lantern Motel

2 out of 5
Price was $924, price is now $864 per person
$864
per person
Dec 29 - Jan 4
found 11 hours ago
Roundtrip non-stop flight included
St. Louis (STL) to Watertown (ATY)
8.8/10 Excellent! (42 reviews)
Nice people…room spacious.

Reviewed on Sep 27, 2025

Grandstay Hotel and Suites Milbank

Grandstay Hotel and Suites Milbank

2.5 out of 5
Price was $1,178, price is now $1,052 per person
$1,052
per person
Dec 29 - Jan 4
found 11 hours ago
Roundtrip non-stop flight included
St. Louis (STL) to Watertown (ATY)
9.4/10 Exceptional! (256 reviews)
Great service, easy check in and check out, quiet, close to restaurant.

Reviewed on Oct 22, 2025

Holiday Inn Express & Suites Watertown by IHG

Holiday Inn Express & Suites Watertown by IHG

2.5 out of 5
Price was $1,067, price is now $972 per person
$972
per person
Dec 29 - Jan 4
found 11 hours ago
Roundtrip non-stop flight included
St. Louis (STL) to Watertown (ATY)
9.6/10 Exceptional! (213 reviews)
Polite staff and quick check in and out.

Reviewed on Sep 29, 2025

Country Inn & Suites by Radisson, Watertown, SD

Country Inn & Suites by Radisson, Watertown, SD

2.5 out of 5
Price was $988, price is now $920 per person
$920
per person
Dec 29 - Jan 4
found 11 hours ago
Roundtrip non-stop flight included
St. Louis (STL) to Watertown (ATY)
8.8/10 Excellent! (927 reviews)
Staff was really nice and room was clean

Reviewed on Oct 18, 2025

Dakota Sioux Casino & Hotel

Dakota Sioux Casino & Hotel

2.5 out of 5
Price was $939, price is now $875 per person
$875
per person
Dec 29 - Jan 4
found 11 hours ago
Roundtrip non-stop flight included
St. Louis (STL) to Watertown (ATY)
8/10 Very Good! (28 reviews)
Roo.s are kinda old

Reviewed on Oct 8, 2025

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Madison Hotel Deals

Cornfield Country House

Cornfield Country House

Hantho Township
10/10 Exceptional! (3 reviews)
Very well kept and spacious. Responsive host as well.

Reviewed on Jul 20, 2025

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Cornfield Country House
Cornfield Country House 1/2

Cornfield Country House 1/2

Hantho Township
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Cornfield Country House 1/2
3-bedroom apartment downtown Madison

3-bedroom apartment downtown Madison

Madison, MN
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3-bedroom apartment downtown Madison
See all 45 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
1,450
Max Temp Winter
20ºF
Max Temp Summer
80ºF

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Frequently asked questions

How much does a Madison vacation package cost?
Offering great value package deals from $864 on Expedia, you'll be surprised at how little a vacation to Madison costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Madison?
If you're hoping to book a cheap Madison vacation package, consider planning a trip in November, December and January. You're likely to find lower rates on airfares and hotels during these months — ideal for a budget-friendly break.
How many days is enough for Madison?
The ideal duration of your Madison vacation depends on what you'd like to do and see. Typically, a few days to a week will give you enough time to tick off all the top sights and explore some hidden treasures along the way.
How to find the best Madison package deals?
Use Expedia's filters to find some terrific Madison package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or look for Madison package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.
Is it cheaper to book a Madison vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging stays and flights individually. Better still, you can personalize your Madison trip to fit your exact needs. 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're planning a spontaneous Madison adventure, check out our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can score incredible deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Madison vacation packages?
Jet off on your perfect trip to Madison with our Book Now, Pay Later vacations. There's no need to scrimp and save or wait for the next payday — we've partnered with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans allow you to spread the cost across 3, 6 or 12 months. With no late payment fees or hidden charges, it's easy to stick to your budget and snap up cheap deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.