Madison Vacation Packages 2026 from $596

Madison flight + hotel vacation packages

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

Holiday Inn Staunton Conference Center by IHG

$596

per person

Oct 13 - Oct 17

found 19 hours ago

Roundtrip non-stop flight included

Houston (IAH) to Weyers Cave (SHD)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.

The Buckhorn - Lodging & Event Venue

$712

per person

Oct 13 - Oct 17

found 19 hours ago

Roundtrip non-stop flight included

Houston (IAH) to Weyers Cave (SHD)

This inn doesn't skimp on freebies - guests receive free WiFi and free self parking. A picnic area, barbecue grills, and a virtual front desk are also on offer.

The Blackburn Inn and Conference Center

$601

per person

Oct 13 - Oct 17

found 19 hours ago

Roundtrip non-stop flight included

Houston (IAH) to Weyers Cave (SHD)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A coffee shop, a terrace, and a garden are also on offer.

Massanuttens Shenandoah Villas by Tripforth

$799

per person

Oct 13 - Oct 17

found 19 hours ago

Roundtrip non-stop flight included

Houston (IAH) to Weyers Cave (SHD)

This aparthotel features an outdoor pool and an indoor pool. Enjoy the gym and perks like free self parking and free WiFi. There's a picnic area and multilingual staff can provide around-the-clock assistance.

Massanutten's Regal Vistas by Tripforth

$985

per person

Oct 13 - Oct 17

found 19 hours ago

Roundtrip non-stop flight included

Houston (IAH) to Weyers Cave (SHD)

This vacation home features an outdoor pool and an indoor pool. Enjoy the gym and perks like free self parking and free WiFi. Multilingual staff can provide around-the-clock assistance and barbecue grills are on offer.

Top Madison hotels deals

Old Rag View Horse Farm with Log Lodge and Treehouse

Madison VA

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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

Massanutten Resort

1822 Resort Dr McGaheysville VA

$102 nightly

$113 total

Sep 9 - Sep 10

Total with taxes and fees

This hotel features a golf course, a full-service spa, and 4 restaurants. 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

$100 total

Sep 27 - Sep 28

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

Skyland

Skyline Dr Mile 41.7 & 42.5 Luray VA

$161 nightly

$187 total

Sep 15 - Sep 16

Total with taxes and fees

A restaurant and a bar/lounge are featured at this hotel. Free self parking and a terrace are also offered on site.

Big Meadows Lodge

Mile 51.2 Skyline Drive Luray VA

$134 nightly

$148 total

Sep 8 - Sep 9

Total with taxes and fees

A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. A fireplace in the lobby and wedding services are also provided.

Pet friendly

Parking included

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

1600 Emmet Street Charlottesville VA

Free Cancellation

$125 nightly

$143 total

Sep 7 - Sep 8

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

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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.

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.

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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 $596. 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.