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.
Ocean 1 Hotel and Suites

Ocean 1 Hotel and Suites

2 out of 5
Downtown Ocean City
Save 100% on your flight
Price was $952, price is now $746 per person
$746
per person
Aug 28 - Sep 2
found 1 hour ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
Free self parking is available and the hotel's front desk is staffed around-the-clock. WiFi in public areas is free. Luggage storage is also provided.
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
North Ocean City
Save 100% on your flight
Price was $1,051, price is now $789 per person
$789
per person
Aug 28 - Sep 2
found 1 hour ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Dine at the beachfront restaurant and relax with beach umbrellas. Family-friendly amenities include an arcade/game room and kid-friendly dining, along with volleyball.
Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5
Price was $1,745, price is now $1,350 per person
$1,350
per person
Sep 5 - Sep 11
found 24 hours ago
Roundtrip non-stop flight included
Columbus (CMH) to Salisbury (SBY)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and conveniences like a 24-hour front desk and laundry facilities.
Monte Carlo Boardwalk Oceanfront Ocean City

Monte Carlo Boardwalk Oceanfront Ocean City

3 out of 5
Downtown Ocean City
Save 100% on your flight
Price was $958, price is now $756 per person
$756
per person
Aug 28 - Sep 2
found 1 hour ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
This smoke-free hotel includes 2 restaurants, an indoor pool, and a hot tub. Enjoy a meal in one of the 2 coffee shops/cafes and free perks like free self parking and WiFi in public areas. Enjoy the seasonal outdoor pool and conveniences like a 24-hour front desk and concierge services.
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Save 100% on your flight
Price was $1,117, price is now $883 per person
$883
per person
Aug 28 - Sep 2
found 1 hour ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
This hotel features 4 restaurants, an outdoor pool, and an indoor pool. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the gym and perks like free WiFi.

Top Madison hotels deals

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
$90 nightly
The price is $99 total per night
$99 total
Aug 17 - Aug 18
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
Free Cancellation
Reserve now, pay when you stay
$296 nightly
The price is $336 total per night
$336 total
Aug 18 - Aug 19
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

Rod 'N' Reel Resort

4 out of 5
4165 Mears Ave Chesapeake Beach MD
Free Cancellation
Reserve now, pay when you stay
$210 nightly
The price is $233 total per night
$233 total
Aug 3 - Aug 4
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
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln St. Michaels MD
$621 nightly
The price is $683 total per night
$683 total
Aug 23 - Aug 24
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
The Tidewater Inn

The Tidewater Inn

3 out of 5
101 E Dover St Easton MD
Free Cancellation
Reserve now, pay when you stay
$156 nightly
The price is $171 total per night
$171 total
Aug 9 - Aug 10
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
The Wildset

The Wildset

2.5 out of 5
209 N Talbot St St. Michaels MD
Free Cancellation
Reserve now, pay when you stay
$272 nightly
The price is $299 total per night
$299 total
Jul 28 - Jul 29
Total with taxes and fees
A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A coffee shop, a snack bar/deli, and concierge services are also on offer.
Breakfast included
Pet friendly
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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 $746. 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.