Madison Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Your Madison Vacation

History, cuisine, art and more … There's a whole lot to discover with a Madison vacation package. And with the ability to easily customize your city getaway, you know it'll be one that's tough to forget. Early Mountain Vineyards is just one of the must-see attractions to check off your to-do list during a trip to Madison. Your Madison vacation is just a few clicks away. Search flights, hotels and more on Expedia for an adventure that's tailored to suit your travel style.

Top Madison Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Little Mod Hotel at the University

Little Mod Hotel at the University

3 out of 5
Venable
Price was CA $1,548, price is now CA $1,319 per person
CA $1,319
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Charlottesville (CHO)
9.2/10 Wonderful! (350 reviews)
Very cute small hotel that is reasonably priced! The rooms were bigger than we expected, and it was great having access to the pool at their sister location on the UVA campus. Would stay here again if I were in Charlottesville.

Reviewed on Jul 6, 2026

Oakhurst Inn at the University

Oakhurst Inn at the University

4 out of 5
Jefferson Park Avenue
Price was CA $1,802, price is now CA $1,437 per person
CA $1,437
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Charlottesville (CHO)
9.2/10 Wonderful! (579 reviews)
Incredible experience! Very relaxing and accommodating. Everyone has been fantastic. My room was perfect. Pool was splendid! Café is great. 10/10

Reviewed on Jul 11, 2026

Dinsmore Boutique Inn

Dinsmore Boutique Inn

4 out of 5
Venable
Price was CA $1,704, price is now CA $1,402 per person
CA $1,402
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Charlottesville (CHO)
9.6/10 Exceptional! (404 reviews)
Wow, the architecture, history, the amenities (especially the guest lounge), and breakfast were all outstanding! We will be back.

Reviewed on Jun 26, 2026

Mayhurst Inn

Mayhurst Inn

3.5 out of 5
Price was CA $1,775, price is now CA $1,481 per person
CA $1,481
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Charlottesville (CHO)
9.2/10 Wonderful! (293 reviews)
This was one of the best stays we have ever had. A truly phenomenal place.

Reviewed on Jun 9, 2026

Massanutten's Regal Vistas by Tripforth

Massanutten's Regal Vistas by Tripforth

3.5 out of 5
Price was CA $2,118, price is now CA $1,905 per person
CA $1,905
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Weyers Cave (SHD)
8.8/10 Excellent! (68 reviews)
Massanutten is a nice getaway.

Reviewed on Jun 8, 2026

Ready to book your vacation to Madison?

 

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Madison Hotel Deals

Massanutten Resort

Massanutten Resort

2.5 out of 5
1822 Resort Dr McGaheysville VA
The price is CA $127 per night from Aug 9 to Aug 10
CA $127
CA $177 total
Aug 9 - Aug 10
includes taxes & fees
8/10 Very good! (1,421 reviews)
"Stayed at Summitt 2 bedrooom unit. Absolutely great stay . Massanutten was clean well maintained with plenty of things to do! Always a pleasure to visit."

Reviewed on Jul 11, 2026

Massanutten Resort
English Inn of Charlottesville

English Inn of Charlottesville

3 out of 5
2000 Morton Drive Charlottesville VA
Fully refundableReserve now, pay when you stay
The price is CA $122 per night from Jul 29 to Jul 30
CA $122
CA $144 total
Jul 29 - Jul 30
includes taxes & fees
9.2/10 Wonderful! (2,933 reviews)
"My stay was great. There was a wasp buzzing around between the window and curtain and I had nothing to swat it with. Called the front desk and the very nice maintenance man was there within 5 minutes and took care of it. Room was very clean, bed was comfortable, good location, breakfast included ..."

Reviewed on Jul 11, 2026

English Inn of Charlottesville
Country Inn & Suites by Radisson, Charlottesville-UVA, VA

Country Inn & Suites by Radisson, Charlottesville-UVA, VA

3 out of 5
1600 Emmet Street Charlottesville VA
Fully refundable
The price is CA $155 per night from Aug 10 to Aug 11
CA $155
CA $177 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (1,184 reviews)
"Clean room, nice staff"

Reviewed on Jul 9, 2026

Country Inn & Suites by Radisson, Charlottesville-UVA, VA
See all 1,798 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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Stay near popular Madison attractions

Early Mountain Vineyards

9.2/10 (24 reviews)
You can enjoy a tasting or tour at Early Mountain Vineyards during your travels to Madison. Discover the mountain views and wineries in this relaxing area.
See properties

What to do in Madison

Great Smoky & Shenandoah National Park Driving Audio Tour

Great Smoky & Shenandoah National Park Driving Audio Tour

CA $38
per traveller
Great Smoky & Shenandoah National Park Driving Audio Tour
Shenandoah National Park Self-Guided Driving Audio Tour

Shenandoah National Park Self-Guided Driving Audio Tour

CA $24
per traveller
100% of travellers recommend
Shenandoah National Park Self-Guided Driving Audio Tour
Discover US East Coast Self Guided Audio Tour

Discover US East Coast Self Guided Audio Tour

CA $206
per traveller
Discover US East Coast Self Guided Audio Tour
See all activities in Madison

Frequently asked questions

How much does a Madison vacation package cost?
Offering great value package deals from CA $1,319 on Expedia, you'll be surprised at how little a vacation to Madison costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Madison?
To pick up cheap Madison vacation packages, plan your trip outside of peak periods such as school holidays. You'll generally find better availability and lower prices in the off-season or when it's less busy.
How many days is enough for Madison?
With a well-planned itinerary, you can easily visit the top Madison attractions in a handful of days. But if you want to discover hidden spots or go on day trips, consider booking your Madison vacation for longer.
How to find the best Madison package deals?
Bagging a cheap Madison package deal is a cinch with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your maximum budget, apply some filters and browse what's available. You can tailor your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to view the most economical Madison package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Madison vacation as a package?
You can enjoy significant savings on your Madison break by booking a customized vacation package. Check the "Package" heading, then enter your destination and travel dates to browse the best airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Madison?
If you've got your Madison travel dates locked in, book as early as you can to bag some outstanding deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for setting off on a whim.
How to plan a trip to Madison?

  1. Choose the ideal time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to visit Madison.
  2. Set your budget: Consider costs like flights, transportation and food when working out how much to save for your trip to Madison. Then, select a hotel that fits your budget, whether that's an affordable option or a deluxe retreat.
  3. Decide your trip length: Consider how much time you'd like to spend exploring Madison. Plan your days so you can get to all the attractions and experiences you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a customized Madison vacation package.

Explore a world of travel with Expedia

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