Madison Vacations from $656
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The Latest Madison vacation packages
Price found within the past 48 hours. Click for updated prices.
Julian Price House
Fisher Park
$656
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
10/10 Exceptional! (155 reviews)
The Julian Price House is amazing and surprising place to stay in the heart of Greensboro. It felt like being in another world.
Reviewed on Aug 12, 2026
King Beds Hot Tub Arcade Grill & Firepit
$1,388
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
9.4/10 Exceptional! (3 reviews)
Loved this little house and all the attention to detail! Would definitely return.
Reviewed on Jun 17, 2026
Pandora's Manor Bed & Breakfast
West High Avenue Historic District
$1,135
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
10/10 Exceptional! (1 review)
Exceptionally beautiful property and exceptional customer service. Graciously accommodated a change in plans, excellent communication throughout, friendly welcome and went the extra mile in all ways to make our very quick trip memorable!
Reviewed on Feb 20, 2026
Madison Hotel Deals
Sheraton Greensboro at Four Seasons
3121 West Gate City Boulevard Greensboro NC
Fully refundableReserve now, pay when you stay
$101 nightly
$114 total
Aug 23 - Aug 24
Total with taxes and fees
9/10 Wonderful! (1,499 reviews)
"We had a good stay!"
Reviewed on Aug 19, 2026
Fairview Inn Airport
6452 Burnt Poplar Rd Greensboro NC
Fully refundableReserve now, pay when you stay
$61 nightly
$69 total
Aug 20 - Aug 21
Total with taxes and fees
Embassy Suites by Hilton Greensboro Airport
204 Centreport Dr Greensboro NC
Fully refundableReserve now, pay when you stay
$96 nightly
$109 total
Aug 30 - Aug 31
Total with taxes and fees
8.2/10 Very Good! (1,167 reviews)
"Check in was unacceptable. We booked a double suite. When we got there, they only had a King suite left. How does that happen when I had reservations? The room had a moldy shower. Only one washcloth. No shampoo and two towels for five people. I was extremely disappointed."
Reviewed on Aug 18, 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 |
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 $656 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.
