Madison Vacations from $443

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The Latest Madison vacation packages

Price found within the past 48 hours. Click for updated prices.
Hawthorne Inn and Conference Center

Hawthorne Inn and Conference Center

3 out of 5
Price was $489, price is now $443 per person
$443
per person
Dec 10 - Dec 13
found 16 hours ago
Roundtrip flight included
New York (NYC) to Greensboro (GSO)
8.6/10 Excellent! (1,301 reviews)
Older room but carpet new. Awkward to get luggage loaded and unloaded. Very strong air freshener in lobby, over powering. Breakfast buffet not worth the 10.00

Reviewed on Nov 1, 2026

StudioRes by Marriott Greensboro Airport

StudioRes by Marriott Greensboro Airport

3 out of 5
Price was $659, price is now $533 per person
$533
per person
Jan 7 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Greensboro (GSO)
9.2/10 Wonderful! (80 reviews)

Proximity Hotel

Proximity Hotel

4 out of 5
Price was $996, price is now $856 per person
$856
per person
Dec 10 - Dec 13
found 16 hours ago
Roundtrip flight included
New York (NYC) to Greensboro (GSO)
9.8/10 Exceptional! (1,000 reviews)
We did have some noise in the early morning of one night, but good otherwise.

Reviewed on Oct 31, 2026

The Shaffner Inn

The Shaffner Inn

2 out of 5
Price was $607, price is now $523 per person
$523
per person
Dec 10 - Dec 13
found 16 hours ago
Roundtrip flight included
New York (NYC) to Greensboro (GSO)
9.2/10 Wonderful! (250 reviews)
This is a beautiful old inn that has timeless charm. Very comfortable space, very clean, and wonderful owner and staff. The breakfast was delicious: fresh scrambled eggs, perfectly cooked stone ground grits, fresh bread for toasting and fresh blueberries and strawberries. The artwork shown in the front rooms was an unexpected plus! So cool! Wifi worked well. An elegant and comfortable stay: thank you!

Reviewed on Nov 1, 2026

Hotel Denim

Hotel Denim

3.5 out of 5
Price was $600, price is now $545 per person
$545
per person
Dec 10 - Dec 13
found 16 hours ago
Roundtrip flight included
New York (NYC) to Greensboro (GSO)
9.2/10 Wonderful! (1,422 reviews)

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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
$61 nightly
The price is $69 total per night from Nov 2 to Nov 3
$69 total
Nov 2 - Nov 3
Total with taxes and fees
7.4/10 Good! (678 reviews)
"Room was nasty"

Reviewed on Nov 1, 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
$110 nightly
The price is $124 total per night from Nov 8 to Nov 9
$124 total
Nov 8 - Nov 9
Total with taxes and fees
Sheraton Greensboro at Four Seasons
Suburban Studios Winston Salem-University Parkway

Suburban Studios Winston Salem-University Parkway

2 out of 5
7910 N Point Blvd Winston-Salem NC
$55 nightly
The price is $62 total per night from Dec 1 to Dec 2
$62 total
Dec 1 - Dec 2
Total with taxes and fees
6.2/10 (1,002 reviews)
"It's to Ghetto for me. I really wouldn't come there again."

Reviewed on Nov 1, 2026

Suburban Studios Winston Salem-University Parkway
See all 902 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 $443 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.