Madison Vacation Packages 2026 from $807

Madison flight + hotel vacation packages

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

Virginia Guesthouse At University Of Virginia

Lewis Mountain

$807

per person

Apr 10 - Apr 12

found 14 hours ago

Roundtrip flight included

New York (NYC) 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.

Little Mod Hotel at the University

Venable

$869

per person

Mar 27 - Mar 29

found 9 hours ago

Roundtrip flight included

New York (NYC) to Charlottesville (CHO)

This hotel features a restaurant, free WiFi in public areas, and a picnic area. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. Express check-in and express check-out are also provided.

Oakhurst Inn at the University

Jefferson Park Avenue

$859

per person

Mar 27 - Mar 29

found 9 hours ago

Roundtrip flight included

New York (NYC) to Charlottesville (CHO)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. A coffee shop, a terrace, and a garden are also on offer.

Dinsmore Boutique Inn

Venable

$875

per person

Mar 27 - Mar 29

found 9 hours ago

Roundtrip flight included

New York (NYC) 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.

Keswick Hall

$1,665

per person

Mar 27 - Mar 29

found 9 hours ago

Roundtrip flight included

New York (NYC) to Charlottesville (CHO)

A golf course, a full-service spa, and 2 outdoor pools are all featured at this smoke-free hotel. Traveling on business? Take advantage of the laundry service and free internet in public areas. Enjoy the 7 outdoor tennis courts and for drinks and a bite to eat, there's a restaurant and bar/lounge.

Top Madison hotels deals

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.

Hot Tub

Kitchen

The Cabin at the Lake

Madison VA

$263 nightly

$290 total

Feb 25 - Feb 26

Total with taxes and fees

This cabin featured laundry facilities and barbecue grills.

Kitchen

Washer

Massanutten Resort

1822 Resort Dr McGaheysville VA

$112 nightly

$124 total

Mar 15 - Mar 16

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.

Pool

Hot Tub

English Inn of Charlottesville

2000 Morton Drive Charlottesville VA

Free Cancellation

Reserve now, pay when you stay

$96 nightly

$109 total

Feb 25 - Feb 26

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.

Pool

Breakfast included

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

1600 Emmet Street Charlottesville VA

Free Cancellation

$105 nightly

$120 total

Mar 16 - Mar 17

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.

Pool

Breakfast included

Holiday Inn Charlottesville-Univ Area by IHG

1901 Emmet St N Charlottesville VA

Free Cancellation

$76 nightly

$86 total

Feb 26 - Feb 27

Total with taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free self parking, a terrace, and a picnic area are also offered.

Parking included

Free WiFi

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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

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.

Madison County Public Library

Madison County Public Library is just one of the places to see in Madison, so why not enjoy the other things to explore during your travels? 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 $807. 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.