Madison Vacations from $484

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The Latest Madison vacation packages

Price found within the past 48 hours. Click for updated prices.
Quality Inn Jonesville I-77

Quality Inn Jonesville I-77

2.5 out of 5
Price was $646, price is now $484 per person
$484
per person
Apr 1 - Apr 8
found 19 hours ago
Roundtrip flight included
New York (JFK) to Greensboro (GSO)
8.4/10 Very Good! (1,005 reviews)
Room was clean if not a bit dated. The motel is being remodeled so only half the motel was available during my stay. Debra at the front desk was helpful and friendly. Breakfast was good, im happy it was sausage patties instead of the gross squishy links at most hotels. The best part? Room 218, the bed was probably in the top 3 best motel beds Ive ever slept in. The sheets were soft, the pad added just an extra bit of comfort on an overall medium firm extremely comfie bed. Down the hill is a Waffle House, next door down the hill, McDonakds. Bojangles, gas station, and Wendys acroos the street.

Reviewed on Jan 4, 2026

O.Henry Hotel

O.Henry Hotel

4 out of 5
Save 100% on your flight
Price was $1,469, price is now $1,039 per person
$1,039
per person
Mar 15 - Mar 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
9.8/10 Exceptional! (724 reviews)
Breakfast menu was limited.

Reviewed on Jan 2, 2026

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 $945, price is now $729 per person
$729
per person
Feb 13 - Feb 16
found 22 hours ago
Roundtrip flight included
New York (NYC) to Greensboro (GSO)
No reviews
The Inn at Elon

The Inn at Elon

3.5 out of 5
Price was $1,478, price is now $1,142 per person
$1,142
per person
Mar 15 - Mar 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
9.6/10 Exceptional! (617 reviews)
Amazing accommodations. Very upscale and comfortable. The restaurant was wonderful. The area is beautiful. This is now at the top of our list to visit. 100% recommend.

Reviewed on Dec 27, 2025

Hotel Denim

Hotel Denim

3.5 out of 5
Price was $627, price is now $485 per person
$485
per person
Feb 16 - Feb 20
just found
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
9/10 Wonderful! (1,015 reviews)
Everything about this place was amazing! It was very clean, breakfast was great, staff was super friendly and helpful. The beds were extremely comfortable. I will definitely stay there every time I visit Greensboro.

Reviewed on Jan 8, 2026

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Madison Hotel Deals

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 $101 total per night from Jan 15 to Jan 16
$101 total
Jan 15 - Jan 16
Total with taxes and fees
8.8/10 Excellent! (934 reviews)
Yes

Reviewed on Jan 5, 2026

DoubleTree by Hilton Greensboro 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 Jan 11 to Jan 12
$105 total
Jan 11 - Jan 12
Total with taxes and fees
8.8/10 Excellent! (1,257 reviews)
Very clean. Some construction that made getting I and out hard

Reviewed on Jan 4, 2026

Sheraton Greensboro at Four Seasons
Hotel Denim

Hotel Denim

3.5 out of 5
1517 Westover Terrace Greensboro NC
Fully refundableReserve now, pay when you stay
$118 nightly
The price is $133 total per night from Jan 11 to Jan 12
$133 total
Jan 11 - Jan 12
Total with taxes and fees
9/10 Wonderful! (1,012 reviews)
This was the coolest hotel I have ever been to in the accommodations were absolutely wonderful compared to any other hotel I’ve been to! 10 out of 10 highly recommend

Reviewed on Jan 6, 2026

Hotel Denim
See all 838 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 $484 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.