Madison Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Choose two or more items and save on your trip:
    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to CA $775 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Your Madison Vacation

The easiest way to experience this exciting city is with a custom-made Madison vacation package. Base yourself in the neighborhood of Downtown Cambridge, which is good for bars and pubs, culture and cafes or go someplace else — our packages are all about you. There's plenty to put on your must-see list during a trip to Madison, beginning with leading attractions such as Harriet Tubman Underground Railroad National Historical Park and Spocott Windmill. Whatever your travel plans or budget, organizing your ultimate tailored Madison vacation is easy with Expedia.

Top Madison Vacation Deals

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

Kokomo Suites

2.5 out of 5
North Ocean City
per person
Jul. 11 - Jul. 14
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
7/10 Good! (115 reviews)
Very nice and convenient kid friendly

Reviewed on Jun. 3, 2024

Club Ocean Villas II by VRI Americas

Club Ocean Villas II by VRI Americas

3.5 out of 5
North Ocean City
per person
Jul. 11 - Jul. 14
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
8.6/10 Excellent! (43 reviews)
Great stay difficult to check in after hours and parking is not clear

Reviewed on May 30, 2023

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
per person
Jul. 11 - Jul. 14
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
8.8/10 Excellent! (2,022 reviews)
Room was clean, staff was friendly. If you need inside room amenities like shampoo, conditioners, they are cheap with that. They don’t even give you a water bottle at check in.

Reviewed on Jun. 8, 2024

Residence Inn by Marriott Ocean City

Residence Inn by Marriott Ocean City

3 out of 5
Midtown Ocean City
per person
Jul. 11 - Jul. 14
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
9/10 Wonderful! (1,005 reviews)
Excellent customer service from staff

Reviewed on Jun. 5, 2024

Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

3 out of 5
North Ocean City
per person
Jul. 11 - Jul. 14
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Salisbury (SBY)
7.8/10 Good! (1,809 reviews)
Pool and being close to ocean.

Reviewed on Jun. 5, 2024

Madison Hotel Deals

Hyatt Regency Chesapeake Bay
Hyatt Regency Chesapeake Bay
4 out of 5
100 Heron Blvd, Cambridge, MD
Fully refundableReserve now, pay when you stay
The price is CA $258 per night from Jul. 8 to Jul. 9
CA $258
CA $350 total
includes taxes & fees
Jul 8 - Jul 9
8.6/10 Excellent! (1,009 reviews)
"Gorgeous property!"

Reviewed on Jun. 4, 2024

Hyatt Regency Chesapeake Bay
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
2.5 out of 5
22769 Three Notch Rd, California, MD
Fully refundableReserve now, pay when you stay
The price is CA $128 per night from Jun. 16 to Jun. 17
CA $128
CA $142 total
includes taxes & fees
Jun 16 - Jun 17
7.4/10 Good! (1,004 reviews)
perfect stay
"great. convenient"

Reviewed on Jun. 5, 2024

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
St Michaels Inn
St Michaels Inn
2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
Fully refundableReserve now, pay when you stay
The price is CA $189 per night from Jun. 23 to Jun. 24
CA $189
CA $208 total
includes taxes & fees
Jun 23 - Jun 24
8/10 Very Good! (1,005 reviews)
"Toilet seat was pealing. Bathroom floor needed a scrub."

Reviewed on May 26, 2024

St Michaels Inn
See all 494 properties in Madison
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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Madison vacation package cost?
Starting from an incredible CA $1,310, you can tailor make your Madison vacation package. Simply combine hotels, flights and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Madison?
It’s as simple as bundling. Hotels, flights and rental cars — combine whatever you need into a Madison vacation package to save loads of cash. Score even more discounts when you add extras such as activities or tours to your booking. But that’s not the only impressive part. You have the flexibility to customize your vacation your own way. We offer over 550 airlines and 1,000,000 hotel options throughout the world, so that everyone has an opportunity to travel and fulfill those vacation fantasies.
How far in advance should I book my Madison vacation?
It all depends on the air carrier, but you can usually browse through international fares on Expedia up to 12 months in advance. While it’s advisable to book ahead of time, lucky travelers occasionally score a cheaper ticket only weeks before the date of departure.
What does an Expedia Madison travel package include?
Flights, car rentals and hotels — we connect you to the best deals. All you’ll have to do is select your ideal combination. Once you’ve made your booking, you can add on the fun stuff like tours and experiences. Our travel packages make it simple to craft an amazing Madison escape.
What should I know before booking a Madison travel package?
Our prices are always low. However, you’ll enjoy an even better deal if you book your flights, hotels and car rentals together. With an Expedia package, you’ll get transparent pricing and loads of choice.
Can I choose my airline with a Madison Expedia vacation package?
Expedia has access to more than 550 partner airlines worldwide, so you sure can! Just choose your preferred air carrier and put together your ideal Madison getaway.
If I'm not able to travel, can I cancel my Madison vacation package?
It’s difficult to predict what tomorrow might bring, so it’s comforting to know that you can cancel or change your Madison vacation package. If your booking was made in the last 24 hours, you may be entitled to a refund. If it’s an older booking, your airline, hotel or car rental company may charge a fee. Check our Customer Service Portal for further details.

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.