Madison Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Madison Vacation Deals

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
per person
Oct 21 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Greensboro (GSO)
8.2/10 Very Good! (1,004 reviews)
Location of this hotel is close to old Salem (walkable). The check in was easy but we had to drive around the hotel to bring our luggage in. The rate was good.

Reviewed on Aug. 3, 2025

Wyndham Garden Greensboro

Wyndham Garden Greensboro

3 out of 5
per person
Oct 21 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Greensboro (GSO)
7.8/10 Good! (1,014 reviews)
Always a great stay!!

Reviewed on Aug. 6, 2025

La Quinta Inn & Suites by Wyndham Greensboro Arpt High Point

La Quinta Inn & Suites by Wyndham Greensboro Arpt High Point

3 out of 5
per person
Oct 21 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Greensboro (GSO)
8.8/10 Excellent! (1,001 reviews)
I didn’t care for their breakfast

Reviewed on Aug. 1, 2025

La Quinta Inn & Suites by Wyndham Greensboro NC

La Quinta Inn & Suites by Wyndham Greensboro NC

3 out of 5
per person
Oct 21 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Greensboro (GSO)
8/10 Very Good! (1,001 reviews)
The location was amazing and the staff was friendly and helpful. An excellent location for our family reunion.

Reviewed on Jul. 22, 2025

Dailey Renewal Retreat Bed & Breakfast

Dailey Renewal Retreat Bed & Breakfast

3 out of 5
Lindley Park
per person
Oct 21 - Oct 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Greensboro (GSO)
9/10 Wonderful! (203 reviews)
This place will always be near and dear to my heart. The breakfast was absolutely delicious, the atmosphere was so cozy and loving I did not want to leave. It was a pleasure to meet Miss Jean Dailey and I hope to come back some time soon. Plus, the house is surrounded by some VERY delicious options for food. If you’re looking for a home-away-from-home getaway, that actually isn’t in the middle of nowhere, I highly recommend!

Reviewed on Aug. 5, 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
The price is CA $142 per night from Aug 14 to Aug 15
CA $142
CA $160 total
Aug 14 - Aug 15
includes taxes & fees
8.8/10 Excellent! (569 reviews)
"Staff was professional and provided excellent customer service"

Reviewed on Aug. 4, 2025

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
The price is CA $151 per night from Aug 10 to Aug 11
CA $151
CA $170 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (1,067 reviews)
"Bef comfort good"

Reviewed on Aug. 1, 2025

Sheraton Greensboro at Four Seasons
Embassy Suites by Hilton Greensboro Airport

Embassy Suites by Hilton Greensboro Airport

3.5 out of 5
204 Centreport Dr, Greensboro, NC
Fully refundableReserve now, pay when you stay
The price is CA $134 per night from Aug 24 to Aug 25
CA $134
CA $151 total
Aug 24 - Aug 25
includes taxes & fees
8.2/10 Very Good! (1,007 reviews)
"Yo"

Reviewed on Jul. 28, 2025

Embassy Suites by Hilton Greensboro Airport
See all 764 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.
All Inclusive Vacations
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Frequently asked questions

How much does a Madison vacation package cost?
Offering great value package deals from CA $1,075 on Expedia, you'll be pleasantly surprised at how much a vacation to Madison costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Madison?
Plan your getaway for the low or shoulder season and you're likely to score cheap Madison vacation packages. Remember that public holidays and major festivals and events can have an impact on prices, so do your research before you go.
How many days is enough for Madison?
The ideal duration for your Madison vacation depends on what you'd like to do. Usually, a handful of days to a week will give you enough time to check out all the main sights and explore some hidden gems along the way.
How to find the best Madison package deals?
Begin your search for a Madison package deal by entering your travel dates and destination under our "Packages" tab. Then add a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Madison package deal straight away, just switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Madison adventure off to a flying start.
Is it cheaper to book a Madison vacation as a package?
You can enjoy significant savings on your Madison retreat by booking a customized vacation package. Click on the "Package" heading, then enter your destination and travel dates to browse the best hotel prices and airfares. Bundle everything into a neat 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 planning a spur-of-the-moment Madison adventure, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can score amazing deals on your flights and hotels by booking ahead.
How to plan a trip to Madison?

  1. Choose when to travel: Check your calendar and pack your bags. Your favourite season and the activities on offer will also help you decide when to vacation in Madison.
  2. Set a budget: Factor in costs like flights, food and transportation when working out how much to set aside for your trip to Madison. Then, select a property that works with your budget, whether that's a low-cost option or a high-end retreat.
  3. Work out your trip length: Consider how long you want to spend exploring Madison. Plan your itinerary so you can get to all the experiences and attractions you're interested in without rushing.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a tailored Madison vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.