Madison Vacations from $392

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The Latest Madison vacation packages

Price found within the past 48 hours. Click for updated prices.
Dailey Renewal Retreat Bed & Breakfast

Dailey Renewal Retreat Bed & Breakfast

3 out of 5
Lindley Park
Price was $491, price is now $392 per person
$392
per person
Mar 19 - Mar 22
found 1 day ago
Roundtrip flight included
New York (NYC) to Greensboro (GSO)
9/10 Wonderful! (207 reviews)
This place will always be near and dear to my heart. The breakfast was absolutely delicious, the atmosphere was so cozy and loving I did not want to leave. It was a pleasure to meet Miss Jean Dailey and I hope to come back some time soon. Plus, the house is surrounded by some VERY delicious options for food. If you’re looking for a home-away-from-home getaway, that actually isn’t in the middle of nowhere, I highly recommend!

Reviewed on Aug 5, 2025

Quality Inn And Suites

Quality Inn And Suites

2.5 out of 5
Price was $797, price is now $624 per person
$624
per person
Apr 23 - Apr 27
found 20 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Greensboro (GSO)
6.2/10 (77 reviews)
Clean rooms and friendly staff

Reviewed on Dec 25, 2025

The Historic Magnolia House

The Historic Magnolia House

3.5 out of 5
Price was $592, price is now $465 per person
$465
per person
Mar 19 - Mar 22
found 1 day ago
Roundtrip flight included
New York (NYC) to Greensboro (GSO)
6/10 (2 reviews)
O.Henry Hotel

O.Henry Hotel

4 out of 5
Price was $885, price is now $747 per person
$747
per person
Apr 9 - Apr 12
found 9 hours ago
Roundtrip flight included
Detroit (DTW) to Greensboro (GSO)
9.8/10 Exceptional! (724 reviews)
Green Valley Grill is fantastic, the hotel has charm, love it!

Reviewed on Jan 18, 2026

Proximity Hotel

Proximity Hotel

4 out of 5
Price was $801, price is now $682 per person
$682
per person
Apr 9 - Apr 12
found 9 hours ago
Roundtrip flight included
Detroit (DTW) to Greensboro (GSO)
9.6/10 Exceptional! (879 reviews)
Great hotel, exceptional service, great restaurant. Will stay here agin when in the area without hesitation

Reviewed on Jan 23, 2026

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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
$130 nightly
The price is $146 total per night from Feb 1 to Feb 2
$146 total
Feb 1 - Feb 2
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 $392 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.