Madison Vacation Packages 2026

Top Madison hotels deals

Hyatt Regency Chesapeake Bay

100 Heron Blvd Cambridge MD

Free Cancellation

Reserve now, pay when you stay

$211 nightly

$240 total

Feb 23 - Feb 24

Total with taxes and fees

This smoke-free resort features a private beach, a golf course, and a full-service spa. Bring the family and enjoy the children's club, mini golf, and children's pool. Enjoy the 2 outdoor pools and perks like free self parking and free WiFi.

On private beach

Pool

Rod 'N' Reel Resort

4165 Mears Ave Chesapeake Beach MD

Free Cancellation

Reserve now, pay when you stay

$119 nightly

$130 total

Feb 24 - Feb 25

Total with taxes and fees

A marina, 2 restaurants, and an indoor pool are all featured at this smoke-free hotel. Make the most of the 24-hour gym and seasonal outdoor pool, and relax with drinks at one of the 2 bars/lounges.

Pool

Spa

St Michaels Inn

1228 S Talbot Street St. Michaels MD

Free Cancellation

Reserve now, pay when you stay

$104 nightly

$115 total

Mar 1 - Mar 2

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the conference center and conference space on site. Enjoy the seasonal outdoor pool and conveniences like a terrace and laundry facilities.

Pool

Breakfast included

Comfort Inn & Suites Lexington Park near Pax River

21885 Three Notch Rd Lexington Park MD

Free Cancellation

Reserve now, pay when you stay

$104 nightly

$116 total

Mar 15 - Mar 16

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. There's a 24-hour gym on site, and a 24-hour front desk and a fireplace in the lobby are also provided.

Breakfast included

Parking included

The Tidewater Inn

101 E Dover St Easton MD

Free Cancellation

Reserve now, pay when you stay

$179 nightly

$197 total

Feb 25 - Feb 26

Total with taxes and fees

This traditional hotel features a full-service spa and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.

Spa

Parking included

Inn at Perry Cabin

308 Watkins Ln St. Michaels MD

$513 nightly

$564 total

Feb 19 - Feb 20

Total with taxes and fees

This luxury hotel features a golf course, a full-service spa, and a marina. Families will appreciate complimentary bicycles, kid-friendly dining, and in-room childcare. Enjoy the 3 outdoor tennis courts and perks like free valet parking and free WiFi.

Pool

Hot Tub

Don't see what you're looking for?

See all available properties in Madison

View all properties

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

Harriet Tubman Underground Railroad National Historical Park

You can spend time studying the exhibits at Harriet Tubman Underground Railroad National Historical Park in Madison. While you're in the area, stroll along the riverfront.

Frequently asked questions

How much are vacation packages to Madison?

Adventure awaits in Madison, with Travelocity vacation packages from as low as . Including both hotels and flights, these sensational deals make it a breeze to visit all corners of the world.

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

Travelocity will be able to help you get an unbeatable Madison package deal. With 400 air carriers and 1,000,000 properties worldwide, there's no doubt you'll be able to put together the perfect itinerary.

Why should I book my Madison vacation package via Travelocity?

We offer 24/7 customer support, high-quality service and a Price Match Guarantee. Life's a great big journey — and we have incredible destinations for you to journey to in all four corners of the globe. Explore with us and make your hip pocket happy.

Will I save money on my Madison car rental if I book it with a hotel or flight?

Combining your car, flight and hotel into a Madison vacation package is an easy way to score the best deal. Plus, having your own set of wheels gives you freedom to make your way to all those famous sights you're hoping to explore. Located 50 mi from Madison, White House is one place that should be on your itinerary. Fill up the tank and make a day trip of it.

Which airport is best for Madison?

For plenty of visitors, a stay in Madison means going through Ronald Reagan Washington National Airport (DCA). This buzzing airport is located 50 mi northwest of the city center. You could also jet into Baltimore Washington Intl. Thurgood Marshall Airport (BWI) (50 mi away from central Madison) or Salisbury - Ocean City Wicomico Regional Airport (SBY) (40 mi away from central Madison).

Where should I stay when visiting Madison?

Many visitors stay at the Farmhouse by the bay! Beach and pier access.. It's sure to be a great base for your Madison escape.