Madison Vacations from $678

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The Latest Madison vacation packages

Price found within the past 48 hours. Click for updated prices.
The Historic Magnolia House

The Historic Magnolia House

3.5 out of 5
Price was $897, price is now $678 per person
$678
per person
Apr 16 - Apr 21
found 23 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Greensboro (GSO)
6/10 (2 reviews)
Hawthorne Inn and Conference Center

Hawthorne Inn and Conference Center

3 out of 5
Price was $1,070, price is now $804 per person
$804
per person
Apr 19 - Apr 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
8.4/10 Very Good! (1,007 reviews)
Room was clean,staff was excellent. Everything was great.

Reviewed on Jan 22, 2026

Kernersville Hot Tub Pool Arcade Gym Wifi Coffee

Kernersville Hot Tub Pool Arcade Gym Wifi Coffee

3 out of 5
Save 100% on your flight
Price was $3,730, price is now $2,877 per person
$2,877
per person
Apr 16 - Apr 21
found 1 day ago
Roundtrip flight included
New York (NYC) to Greensboro (GSO)
6/10 (4 reviews)
Heated Pool King Bed Jacuzzi Bath Arcade

Heated Pool King Bed Jacuzzi Bath Arcade

4 out of 5
Save 100% on your flight
Price was $1,679, price is now $1,301 per person
$1,301
per person
Apr 16 - Apr 21
found 1 day ago
Roundtrip flight included
New York (NYC) to Greensboro (GSO)
8/10 Very Good! (1 review)
The house was very clean, comfortable, and nicely maintained, which we really appreciated during our stay. However, there were two downsides to be aware of. First, after booking, the owner asked us to pay an extra money for cleaning fee, even though it was not clearly listed in the Expedia booking details. I chose not to argue since I didn’t want to ruin our family trip, but future guests should expect additional charges. Second, privacy was an issue the owner lives in the basement, and it felt uncomfortable at times, especially with my child playing and moving around. Overall, it’s a nice property, but keep in mind the extra costs and limited privacy.

Reviewed on Sep 30, 2025

Winston Sleeps 16 - 2 Kitchens Hot Tub

Winston Sleeps 16 - 2 Kitchens Hot Tub

3.5 out of 5
Save 100% on your flight
Price was $1,442, price is now $1,123 per person
$1,123
per person
Apr 16 - Apr 21
found 1 day ago
Roundtrip flight included
New York (NYC) to Greensboro (GSO)
No reviews
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Madison Hotel Deals

Sheraton Greensboro at Four Seasons

Sheraton Greensboro at Four Seasons

3.5 out of 5
3121 West Gate City Boulevard Greensboro NC
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $114 total per night from Feb 3 to Feb 4
$114 total
Feb 3 - Feb 4
Total with taxes and fees
8.8/10 Excellent! (1,285 reviews)
My stay was pleasant and my room was very clean. This hotel needs more elevators to accommodate all of its guest. We had to wait 10 minutes for an elevator. Once we got one we had to pack 11-12 people on it.

Reviewed on Jan 21, 2026

Sheraton Greensboro at Four Seasons
DoubleTree by Hilton Greensboro Airport

DoubleTree by Hilton Greensboro Airport

4 out of 5
6426 Burnt Poplar Road Greensboro NC
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $92 total per night from Feb 8 to Feb 9
$92 total
Feb 8 - Feb 9
Total with taxes and fees
8.8/10 Excellent! (961 reviews)
Excellent experience.

Reviewed on Jan 24, 2026

DoubleTree by Hilton Greensboro Airport
Hotel Denim

Hotel Denim

3.5 out of 5
1517 Westover Terrace Greensboro NC
Fully refundableReserve now, pay when you stay
$121 nightly
The price is $136 total per night from Jan 29 to Jan 30
$136 total
Jan 29 - Jan 30
Total with taxes and fees
9/10 Wonderful! (1,013 reviews)
The room and public areas were very clean. The staff were friendly and welcoming. Parking lot was well lighted and in view of the lobby check in desk. Planning on staying again.

Reviewed on Jan 20, 2026

Hotel Denim
See all 853 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
Closest Airport
Piedmont Triad Intl. Airport (GSO)
Population
2,200
Max Temp Winter
50ºF
Max Temp Summer
90ºF

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Frequently asked questions

How much does a Madison vacation package cost?
Offering excellent value package deals from $678 on Expedia, you'll be surprised at how little a vacation to Madison costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Madison?
You're likely to find lower rates and better availability in August, September and October. Browse our cheap Madison vacation packages and you could score some excellent off-season deals.
How many days is enough for Madison?
With a well-organized travel plan, you can easily visit the main Madison attractions in a handful of days. But if you'd like to explore off the beaten track or go on day tours, think about booking your Madison vacation for longer.
How to find the best Madison package deals?
Use Expedia's filters to help you find some great Madison package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking 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 score even better discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Madison vacation as a package?
You can enjoy significant savings on your Madison getaway by booking a personalized vacation package. Check the "Package" heading, then enter your travel dates and destination to browse the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Madison?
If you're considering an impromptu Madison trip, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can land sensational deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Madison vacation packages?
If you're like us, you love traveling but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the cost of your Madison trip over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure great vacation packages with payment plans as soon as you spot them.

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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.