Deals on vacations and trips to Madison

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Madison flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel 24 South

Hotel 24 South

3 out of 5
Price was $441, price is now $356 per person
$356
per person
Nov 6 - Nov 8
found 1 day ago
Roundtrip flight included
Miami (MIA) to Weyers Cave (SHD)
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Relax with a drink at the bar/lounge and enjoy perks like free WiFi. Self parking, a 24-hour business center, and a lobby fireplace are also offered.
Little Mod Hotel at the University

Little Mod Hotel at the University

3 out of 5
Venable
Price was $1,006, price is now $718 per person
$718
per person
Nov 6 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) 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

Oakhurst Inn at the University

4 out of 5
Jefferson Park Avenue
Price was $1,135, price is now $943 per person
$943
per person
Nov 6 - Nov 8
found 5 hours ago
Roundtrip non-stop flight included
Miami (MIA) 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. Enjoy the sauna and conveniences like a 24-hour front desk and concierge services.
English Inn of Charlottesville

English Inn of Charlottesville

3 out of 5
The Meadows
Price was $950, price is now $794 per person
$794
per person
Oct 22 - Oct 25
found 17 hours ago
Roundtrip flight included
President Donald J. Trump Intl. Airport (DJT) 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.
Bluegreen Vacations Shenandoah Crossing, an Ascend Collection Resort

Bluegreen Vacations Shenandoah Crossing, an Ascend Collection Resort

2.5 out of 5
Price was $982, price is now $833 per person
$833
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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.

Top Madison hotels deals

Massanutten Resort

Massanutten Resort

2.5 out of 5
1822 Resort Dr McGaheysville VA
$104 nightly
The price is $114 total per night
$114 total
Sep 23 - Sep 24
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.
Pool
Hot Tub
English Inn of Charlottesville

English Inn of Charlottesville

3 out of 5
2000 Morton Drive Charlottesville VA
Free Cancellation
Reserve now, pay when you stay
$79 nightly
The price is $90 total per night
$90 total
Oct 14 - Oct 15
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

Skyland

2 out of 5
Skyline Dr Mile 41.7 & 42.5 Luray VA
$172 nightly
The price is $198 total per night
$198 total
Sep 27 - Sep 28
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
Big Meadows Lodge

Big Meadows Lodge

3 out of 5
Mile 51.2 Skyline Drive Luray VA
$136 nightly
The price is $150 total per night
$150 total
Sep 15 - Sep 16
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

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

3 out of 5
1600 Emmet Street Charlottesville VA
Free Cancellation
$110 nightly
The price is $125 total per night
$125 total
Oct 4 - Oct 5
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

Holiday Inn Charlottesville-Univ Area by IHG

3 out of 5
1901 Emmet St N Charlottesville VA
Free Cancellation
$93 nightly
The price is $106 total per night
$106 total
Sep 27 - Sep 28
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.

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 $356. 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.

Photos of local treasures

Browse Madison vacation photos for more inspiration

A large pink building with a blue roof, surrounded by a well-maintained lawn and dense trees.
A green barn with a white roof, surrounded by a wooden fence and trees.
A forest path with a mulch-covered trail, surrounded by various flowering plants and trees.
A mountainous landscape with dense green forests and a clear blue sky with scattered clouds.
A Tastee Freez store with a red and white checkered border, located in a parking lot with trees in the background.