Madison Vacations from $464

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The Latest Madison vacation packages

Price found within the past 48 hours. Click for updated prices.
Greenwood Bed & Breakfast

Greenwood Bed & Breakfast

3 out of 5
Fisher Park
Price was $632, price is now $464 per person
$464
per person
Nov 13 - Nov 16
found 13 hours ago
Roundtrip non-stop flight included
Houston (HOU) to Greensboro (GSO)
9.2/10 Wonderful! (45 reviews)
This location is a beautiful old house in an amazing historic area. It was very convenient to the rehearsal dinner and wedding venue that we were there to attend. The house itself needs a good bit of cosmetic work, it was pretty cluttered inside. The host had family members staying there as well who were noisy and disruptive. The bed was comfortable, the host was attentive and helpful. The breakfasts were very good. It wasn’t quite as clean as I like, I am pretty particular about that.

Reviewed on Jul 13, 2025

Julian Price House

Julian Price House

3 out of 5
Fisher Park
Price was $1,830, price is now $487 per person
$487
per person
Nov 12 - Nov 16
found 12 hours ago
Roundtrip non-stop flight included
Houston (HOU) to Greensboro (GSO)
10/10 Exceptional! (103 reviews)
The staff was very detailed and organized with my arrival being that I flew in from KY at midnight. The interior and exterior design is EXQUISITE! My communication with the staff was always very pleasant and professional via text. I will be booking another stay the next time I’m in NC.

Reviewed on Aug 15, 2025

O.Henry Hotel

O.Henry Hotel

4 out of 5
Save 100% on your flight
Price was $1,006, price is now $685 per person
$685
per person
Nov 12 - Nov 16
found 12 hours ago
Roundtrip non-stop flight included
Houston (HOU) to Greensboro (GSO)
9.8/10 Exceptional! (687 reviews)
The design of the hotel and the special events like Jazz night and Tea in the afternoon were a delight.

Reviewed on Jul 21, 2025

The Historic Brookstown Inn, Trademark Collection by Wyndham

The Historic Brookstown Inn, Trademark Collection by Wyndham

3.5 out of 5
Price was $680, price is now $539 per person
$539
per person
Nov 13 - Nov 16
found 13 hours ago
Roundtrip non-stop flight included
Houston (HOU) to Greensboro (GSO)
9.6/10 Exceptional! (1,010 reviews)
Beautiful one of a kind historic landmark.

Reviewed on Aug 27, 2025

Proximity Hotel

Proximity Hotel

4 out of 5
Price was $1,032, price is now $821 per person
$821
per person
Nov 12 - Nov 16
found 12 hours ago
Roundtrip non-stop flight included
Houston (HOU) to Greensboro (GSO)
9.6/10 Exceptional! (840 reviews)
Loved everything about the hotel

Reviewed on Aug 19, 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
$103 nightly
The price is $116 total per night from Sep 3 to Sep 4
$116 total
Sep 3 - Sep 4
Total with taxes and fees
8.8/10 Excellent! (616 reviews)
"I stay at this property each time i visit Greensboro"

Reviewed on Aug 23, 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
Fully refundableReserve now, pay when you stay
$74 nightly
The price is $83 total per night from Sep 4 to Sep 5
$83 total
Sep 4 - Sep 5
Total with taxes and fees
8.2/10 Very Good! (1,010 reviews)
"Staff was very responsive to a problem with my entry key and corrected it promptly"

Reviewed on Aug 24, 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 Sep 7 to Sep 8
$124 total
Sep 7 - Sep 8
Total with taxes and fees
8.8/10 Excellent! (1,085 reviews)
"I would stay there again."

Reviewed on Aug 25, 2025

Sheraton Greensboro at Four Seasons
See all 771 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.

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Frequently asked questions

How much does a Madison vacation package cost?
Offering excellent value package deals from $464 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.