Madison Vacation Packages 2026 from $499

Madison flight + hotel vacation packages

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

Bluegreen Vacations Shenandoah Crossing, an Ascend Collection Resort

$499

per person

Apr 2 - Apr 5

found 1 day ago

Roundtrip non-stop flight included

Portland (PWM) to Charlottesville (CHO)

2 outdoor pools, a hot tub, and a gym are all featured at this hotel. There's fun for all ages with a children's pool and a playground, and families will appreciate the onsite laundry facilities. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi.

Shenandoah Wilderness Traveler

$504

per person

Apr 2 - Apr 5

found 1 day ago

Roundtrip non-stop flight included

Portland (PWM) to Charlottesville (CHO)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden, laundry facilities, and barbecue grills are also on offer.

Virginia Guesthouse At University Of Virginia

Lewis Mountain

$626

per person

May 1 - May 3

found 1 day ago

Roundtrip non-stop flight included

Portland (PWM) to Charlottesville (CHO)

A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. A 24-hour business center, a coffee shop, and a snack bar/deli are also on offer.

Dinsmore Boutique Inn

Venable

$730

per person

May 1 - May 3

found 1 day ago

Roundtrip non-stop flight included

Portland (PWM) to Charlottesville (CHO)

This bed & breakfast doesn't skimp on freebies - guests receive free cooked-to-order breakfast, free WiFi, and free self parking. Business travelers can take advantage of the express check-out. A terrace, concierge services, and wedding services are also on offer.

Graduate by Hilton Charlottesville

Venable

$943

per person

Apr 2 - Apr 5

found 1 day ago

Roundtrip non-stop flight included

Portland (PWM) to Charlottesville (CHO)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a coffee shop, and a terrace are also offered.

Top Madison hotels deals

The Cabin at the Lake

Madison VA

$257 nightly

$283 total

Feb 8 - Feb 9

Total with taxes and fees

This cabin featured laundry facilities and barbecue grills.

Kitchen

Washer

Old Rag View Horse Farm with Log Lodge and Treehouse

Madison VA

Get rates

A hot tub is featured at this vacation home, along with a garden and laundry facilities. Families will appreciate the arcade/game room and barbecue grills.

Massanutten Resort

1822 Resort Dr McGaheysville VA

$130 nightly

$144 total

Feb 9 - Feb 10

Total with taxes and fees

This hotel features a golf course, a full-service spa, and a water park. Take advantage of ski lessons, ski rentals and ski passes on site, and enjoy snowboarding. There's fun for all ages with mini golf and a children's pool, and families will appreciate the onsite laundry facilities.

English Inn of Charlottesville

2000 Morton Drive Charlottesville VA

Free Cancellation

Reserve now, pay when you stay

$88 nightly

$101 total

Feb 19 - Feb 20

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

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

1600 Emmet Street Charlottesville VA

Free Cancellation

$101 nightly

$116 total

Feb 26 - Feb 27

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Kimpton The Forum Hotel by IHG

540 Massie Road Charlottesville VA

Free Cancellation

$175 nightly

$200 total

Feb 9 - Feb 10

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 10 conference rooms on site, along with the valet parking and WiFi in public areas. A garden, a communal living room, and luggage storage are also on offer.

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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.

Popular places to visit

Early Mountain Vineyards

4.5/5(19 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.

Madison Plaza

You can enjoy retail therapy at Madison Plaza during your stay in Madison. You can seek out the hiking trails in this family-friendly area.

Lawrence Beasley Park

Explore the great outdoors at Lawrence Beasley Park, a lovely green space in Madison. You can seek out the hiking trails in this family-friendly area.

Frequently asked questions

How much are vacation packages to Madison?

Spoil yourself with a fulfilling travel experience in Madison with a vacation package starting from just $499. Organizing your hotels, tours and flights with Travelocity is simple. And even better, our great deals will leave you with more savings for plenty of fun activities.

How long should my Madison vacation be?

If you need some guidance, most visitors spend about 2 nights in Madison. But to uncover the true spirit of this place, stay a bit longer. That way you can get to more attractions and really experience the local culture.

Where can I get the best vacation package deals for Madison?

With as many as 400 airlines and 1,000,000 properties all over the world, you can't go wrong with Travelocity. Take advantage of our comprehensive range and create your dream Madison vacation package. Don't you just love it when travel is that easy?

Why should I book my Madison vacation package with Travelocity?

We make traveling the world easy. Whether you're searching for an amazing new place to roam around or want to make sure you get the best deal around, we're here to help. Our 24/7 customer care, excellent service and Price Match Guarantee mean you can book with confidence.

Can I save money on my Madison car rental if I book it with hotels and flights?

Bundling your car, flight and hotel into a Madison vacation package is an excellent way to land the best deal. Plus, having your own set of wheels gives you total freedom to get to all those amazing sights you're itching to see. Sitting 75 mi away from Madison, White House is one place that should be on your to-do list. Load up the car and make a day trip of it.

Which airport is best for Madison?

Washington Dulles Intl. Airport (IAD) is a main hub. You'll find it roughly 60 mi northeast of Madison. Your other options are Charlottesville-Albemarle Airport (CHO) (20 mi away from central Madison) and Shenandoah Valley Regional Airport (SHD) (35 mi away from central Madison).

What is there to do in Madison?

Early Mountain Vineyards is one of the memorable sights that make Madison such a popular destination. But give yourself enough time to experience its lesser-known attractions too. This is sometimes where the best memories are made.

Where should I stay when visiting Madison?

The The Ebenezer House Bed And Breakfast is recommended by many visitors. Book soon to avoid missing out.