Madison Vacations from $395

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The Latest Madison vacation packages

Price found within the past 48 hours. Click for updated prices.
Julian Price House

Julian Price House

3 out of 5
Fisher Park
Price was $1,035, price is now $395 per person
$395
per person
Dec 4 - Dec 6
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
10/10 Exceptional! (105 reviews)
From the start, I knew this was not a another mondain, casual experience. The historical charm, quaint decor and extremely manicured property became soothing and transcended us back in time. Just WOW! The online pictures are accurate but the experiencing the history and beauty of this mansion is amazing.

Reviewed on Sep 30, 2025

Greenwood Bed & Breakfast

Greenwood Bed & Breakfast

3 out of 5
Fisher Park
Price was $574, price is now $439 per person
$439
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Greensboro (GSO)
9.4/10 Exceptional! (48 reviews)
Quiet neighborhood. Nice 120 year old home. Very pleasant and responsive host. Parking directly across the street. Breakfast was delicious and plentiful. Even brought home a couple of freshly picked Japanese Persimmon fruit. Would stay again.

Reviewed on Oct 12, 2025

Heated Pool King Bed Jacuzzi Bath Arcade

Heated Pool King Bed Jacuzzi Bath Arcade

4 out of 5
Save 100% on your flight
Price was $1,561, price is now $1,218 per person
$1,218
per person
Dec 4 - Dec 6
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
No reviews
The house was very clean, comfortable, and nicely maintained, which we really appreciated during our stay. However, there were two downsides to be aware of. First, after booking, the owner asked us to pay an extra money for cleaning fee, even though it was not clearly listed in the Expedia booking details. I chose not to argue since I didn’t want to ruin our family trip, but future guests should expect additional charges. Second, privacy was an issue the owner lives in the basement, and it felt uncomfortable at times, especially with my child playing and moving around. Overall, it’s a nice property, but keep in mind the extra costs and limited privacy.

Reviewed on Sep 30, 2025

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 $1,412, price is now $1,108 per person
$1,108
per person
Dec 4 - Dec 6
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
No reviews
O.Henry Hotel

O.Henry Hotel

4 out of 5
Price was $615, price is now $489 per person
$489
per person
Dec 4 - Dec 6
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Greensboro (GSO)
9.8/10 Exceptional! (699 reviews)
Everything was perfect!!

Reviewed on Sep 30, 2025

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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 Oct 19 to Oct 20
$101 total
Oct 19 - Oct 20
Total with taxes and fees
8.8/10 Excellent! (719 reviews)
"Wish the bar stayed open later than 10 but was great, little bit pricey but bartender was great!"

Reviewed on Oct 8, 2025

DoubleTree by Hilton Greensboro Airport
Four Points by Sheraton Greensboro Airport

Four Points by Sheraton Greensboro Airport

3 out of 5
7619 Thorndike Rd, Greensboro, NC
$70 nightly
The price is $79 total per night from Oct 19 to Oct 20
$79 total
Oct 19 - Oct 20
Total with taxes and fees
8.2/10 Very Good! (1,011 reviews)
"The staff was super nice and helpful!"

Reviewed on Oct 5, 2025

Four Points by Sheraton 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
$110 nightly
The price is $124 total per night from Nov 9 to Nov 10
$124 total
Nov 9 - Nov 10
Total with taxes and fees
8.8/10 Excellent! (1,130 reviews)
"I stayed here because it was close to the location I had to get surgery. And my #1 reasoning for picking this hotel was in hopes of having a comfortable bed.. Let me tell you. It was not a disappointment.. The bed was absolutely amazing !! I requested extra pillows and they provided them with no ..."

Reviewed on Oct 6, 2025

Sheraton Greensboro at Four Seasons
See all 797 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.

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 $395 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.