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Madison flight + hotel vacation packages

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Cayman Suites Hotel

Cayman Suites Hotel

2 out of 5
North Ocean City
Price was $899, price is now $879 per person
$879
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Salisbury (SBY)
This hotel features an indoor pool and a gym. Business travelers can take advantage of the free WiFi in public areas. Free self parking, concierge services, and free newspapers are also on offer.
Majestic Hotel & Apartments

Majestic Hotel & Apartments

2 out of 5
Downtown Ocean City
Price was $925, price is now $892 per person
$892
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Salisbury (SBY)
A seasonal outdoor pool, self parking, and concierge services are featured at this aparthotel. A grocery/convenience store, a picnic area, and barbecue grills are also on offer.
Eden Roc Ocean Front

Eden Roc Ocean Front

2 out of 5
Downtown Ocean City
Price was $931, price is now $909 per person
$909
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Salisbury (SBY)
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A seasonal outdoor pool is also provided.
Club Ocean Villas II by Coolvacay

Club Ocean Villas II by Coolvacay

3.5 out of 5
North Ocean City
Price was $986, price is now $964 per person
$964
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Salisbury (SBY)
A marina and an indoor pool are featured at this smoke-free apartment. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. Enjoy the hot tub and conveniences like a picnic area and a virtual front desk.
Coastal Palms Inn & Suites

Coastal Palms Inn & Suites

3 out of 5
North Ocean City
Price was $891, price is now $883 per person
$883
per person
Oct 16 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Salisbury (SBY)
This resort features a restaurant, a seasonal outdoor pool, and a bar/lounge. There's no skimping on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Express check-out, laundry facilities, and concierge services are also on offer.

Top Madison hotels deals

Rod 'N' Reel Resort

Rod 'N' Reel Resort

4 out of 5
4165 Mears Ave Chesapeake Beach MD
Free Cancellation
Reserve now, pay when you stay
$132 nightly
The price is $146 total per night
$146 total
Oct 15 - Oct 16
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

St Michaels Inn

2.5 out of 5
1228 S Talbot Street St. Michaels MD
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $102 total per night
$102 total
Oct 15 - Oct 16
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
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd Cambridge MD
$266 nightly
The price is $302 total per night
$302 total
Sep 29 - Sep 30
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
avid hotel California - Lexington Park by IHG

avid hotel California - Lexington Park by IHG

3 out of 5
23274 Three Notch Road California MD
Free Cancellation
$97 nightly
The price is $108 total per night
$108 total
Sep 24 - Sep 25
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast and free WiFi. Business travelers can take advantage of the 24-hour business center. There's a gym on site, and a 24-hour front desk and a snack bar/deli are also provided.
Breakfast included
Pet friendly
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

3 out of 5
22769 Three Notch Rd California MD
Free Cancellation
Reserve now, pay when you stay
$94 nightly
The price is $105 total per night
$105 total
Sep 20 - Sep 21
Total with taxes and fees
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. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
The Tidewater Inn

The Tidewater Inn

3 out of 5
101 E Dover St Easton MD
$186 nightly
The price is $205 total per night
$205 total
Oct 15 - Oct 16
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.
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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

Harriet Tubman Underground Railroad National Historical Park

9.6/10 (95 reviews)
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.
See properties

Frequently asked questions

How much are vacation packages to Madison?
Adventure awaits in Madison, with Travelocity vacation packages from as low as $879. 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.

Photos of local treasures

Browse Madison vacation photos for more inspiration

A mural of a boat with people and a quote about praying to God.
A modern building with large glass windows, a metal roof, and a small tree in the foreground.
A sculpture of a woman in a field, a quote on the wall, and a display case with a model.
A statue of a person holding a child, with a quote about family and slavery on the wall behind.