Madison Vacations from $527

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The Latest Madison vacation packages

Price found within the past 48 hours. Click for updated prices.
Microtel Inn by Wyndham Greensboro

Microtel Inn by Wyndham Greensboro

2 out of 5
Price was $626, price is now $527 per person
$527
per person
Jul 27 - Aug 2
found 20 hours ago
Roundtrip flight included
New York (NYC) to Greensboro (GSO)
7.4/10 Good! (1,003 reviews)
The place was nice and everything was really nice and 100% clean. This is way I always go there.and the staff is really nice as well and really helpful.

Reviewed on Jun 8, 2026

O.Henry Hotel

O.Henry Hotel

4 out of 5
Save 100% on your flight
Price was $1,407, price is now $1,055 per person
$1,055
per person
Jul 27 - Aug 2
found 20 hours ago
Roundtrip flight included
New York (NYC) to Greensboro (GSO)
9.8/10 Exceptional! (807 reviews)
breakfast wasn’t that great

Reviewed on Jun 3, 2026

Proximity Hotel

Proximity Hotel

4 out of 5
Price was $743, price is now $641 per person
$641
per person
Aug 14 - Aug 16
just found
Roundtrip flight included
New York (NYC) to Greensboro (GSO)
9.8/10 Exceptional! (1,002 reviews)
The staff was extremely pleasant and professional. We were greeted warmly! The room was not as clean it should be. The curtains had stains on them.

Reviewed on Jun 8, 2026

Julian Price House

Julian Price House

3 out of 5
Fisher Park
Price was $680, price is now $593 per person
$593
per person
Aug 14 - Aug 16
just found
Roundtrip flight included
New York (NYC) to Greensboro (GSO)
10/10 Exceptional! (137 reviews)
Beautiful house, comfortable bed, everyone was friendly!

Reviewed on Jun 2, 2026

Holiday Inn Greensboro Coliseum by IHG

Holiday Inn Greensboro Coliseum by IHG

3 out of 5
Price was $800, price is now $723 per person
$723
per person
Jul 27 - Aug 2
found 20 hours ago
Roundtrip flight included
New York (NYC) to Greensboro (GSO)
9/10 Wonderful! (1,001 reviews)
Room was very clean. Staff was friendly and courteous.

Reviewed on Jun 12, 2026

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Madison Hotel Deals

Fairview Inn Airport

Fairview Inn Airport

2.5 out of 5
6452 Burnt Poplar Rd Greensboro NC
Fully refundableReserve now, pay when you stay
$54 nightly
The price is $61 total per night from Jun 28 to Jun 29
$61 total
Jun 28 - Jun 29
Total with taxes and fees
7.4/10 Good! (324 reviews)
"It’s nice and comfy"

Reviewed on Jun 14, 2026

Fairview Inn Airport
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
$93 nightly
The price is $105 total per night from Jul 5 to Jul 6
$105 total
Jul 5 - Jul 6
Total with taxes and fees
9/10 Wonderful! (1,412 reviews)
"Spacious room and the food was good"

Reviewed on Jun 12, 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
$89 nightly
The price is $100 total per night from Jun 25 to Jun 26
$100 total
Jun 25 - Jun 26
Total with taxes and fees
8.8/10 Excellent! (1,258 reviews)
"I thought the breakfast would’ve been a free buffet but it was menu and expensive."

Reviewed on Jun 12, 2026

DoubleTree by Hilton Greensboro Airport
See all 833 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 $527 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.