Madison Vacation Packages 2025/2026 from $610

Madison flight + hotel vacation packages

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

English Inn of Charlottesville

The Meadows

$610

per person

Oct 18 - Oct 19

found 1 day ago

Roundtrip non-stop flight included

Portland (PDX) to Charlottesville (CHO)

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.

The Inn At Warm Springs

$660

per person

Nov 7 - Nov 9

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Weyers Cave (SHD)

A restaurant and a bar/lounge are featured at this inn. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A coffee shop, a terrace, and a garden are also on offer.

Little Mod Hotel at the University

Venable

$788

per person

Oct 18 - Oct 19

found 1 day ago

Roundtrip non-stop flight included

Portland (PDX) 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.

Sonesta ES Suites Charlottesville University

Barracks Road

$642

per person

Oct 18 - Oct 19

found 1 day ago

Roundtrip non-stop flight included

Portland (PDX) to Charlottesville (CHO)

This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.

Oakhurst Inn at the University

Jefferson Park Avenue

$810

per person

Oct 18 - Oct 19

found 1 day ago

Roundtrip non-stop flight included

Portland (PDX) to Charlottesville (CHO)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling for business? Take advantage of the free WiFi in public areas, express check-out, and conference space. Self parking, a coffee shop, and a terrace are also offered.

Top Madison hotels deals

English Inn of Charlottesville

2000 Morton Drive, Charlottesville, VA

$88 nightly

$101 total

Sep 28 - Sep 29

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

Massanutten Resort

1822 Resort Dr, McGaheysville, VA

$114 nightly

$126 total

Sep 11 - Sep 12

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

Extended Stay America Premier Suites - Charlottesville

3400 Berkmar Drive, Charlottesville, VA

Free Cancellation

Reserve now, pay when you stay

$83 nightly

$94 total

Sep 21 - Sep 22

Total with taxes and fees

A 24-hour gym, free self parking, and laundry facilities are featured at this hotel. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. Luggage storage and barbecue grills are also provided.

Breakfast included

Pet friendly

Skyland

Skyline Dr Mile 41.7 & 42.5, Luray, VA

$147 nightly

$169 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.

Pet friendly

Parking included

DoubleTree by Hilton Hotel Charlottesville

990 Hilton Heights Rd, Charlottesville, VA

$93 nightly

$107 total

Sep 28 - Sep 29

Total with taxes and fees

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

Pool

Free airport shuttle

Days Inn by Wyndham Charlottesville/University Area

1610 Emmet St N, Charlottesville, VA

Free Cancellation

Reserve now, pay when you stay

$89 nightly

$102 total

Sep 14 - Sep 15

Total with taxes and fees

This motel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. Luggage storage, laundry facilities, and free newspapers are also on offer.

Breakfast included

Parking 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.

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.

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.

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 $610. 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.