Madison Vacation Packages
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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.
Sahara Motel
Downtown Ocean City
Price was CA $2,698, price is now CA $2,245 per person
CA $2,245
per person
Jun 21 - Jun 28
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Salisbury (SBY)
7.6/10 Good! (536 reviews)
The overall room and property cleanliness, room view and helpful staff service was at a very high level
Of standards …
This is coming from someone that has stayed at multiple hotels in many different vacation and non vacation destinations
HIGHLY RECOMMENDED….
Reviewed on May 15, 2026
Grand Hotel Ocean City Oceanfront
Downtown Ocean City
Price was CA $4,337, price is now CA $3,514 per person
CA $3,514
per person
Jun 21 - Jun 28
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Salisbury (SBY)
9/10 Wonderful! (3,531 reviews)
Clean room, great indoor pool. Overall, I would recommend this hotel. We had a wonderful experience.
Reviewed on May 14, 2026
Hampton Inn & Suites Ocean City/Bayfront-Convention Center
Midtown Ocean City
Price was CA $4,024, price is now CA $3,290 per person
CA $3,290
per person
Jun 21 - Jun 28
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Salisbury (SBY)
8.8/10 Excellent! (1,000 reviews)
The price was good and the stay was also good.
Reviewed on May 15, 2026
Princess Bayside Beach Hotel
Midtown Ocean City
Price was CA $3,074, price is now CA $2,652 per person
CA $2,652
per person
Jun 21 - Jun 28
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Salisbury (SBY)
8/10 Very Good! (1,002 reviews)
Thank you, we will be back during the summer time
Reviewed on Apr 6, 2026
Hotel Monte Carlo Ocean City
Downtown Ocean City
Price was CA $3,020, price is now CA $2,614 per person
CA $2,614
per person
Jun 21 - Jun 28
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Salisbury (SBY)
7.8/10 Good! (1,004 reviews)
Very good experience !!! The staff was very nice and accommodating.The younger female worker is an amazing worker ! We will definitely be back this summer when it is hot. Loved the area because it had many stores around.
Reviewed on Apr 26, 2026
Madison Hotel Deals
Hyatt Regency Chesapeake Bay
100 Heron Blvd Cambridge MD
Fully refundableReserve now, pay when you stay
The price is CA $323 per night from May 19 to May 20
CA $323
CA $432 total
May 19 - May 20
includes taxes & fees
Rod 'N' Reel Resort
4165 Mears Ave Chesapeake Beach MD
Fully refundableReserve now, pay when you stay
The price is CA $175 per night from May 26 to May 27
CA $175
CA $221 total
May 26 - May 27
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
Nice location
Reviewed on May 12, 2026
Inn at Perry Cabin
308 Watkins Ln St. Michaels MD
The price is CA $827 per night from May 31 to Jun 1
CA $827
CA $910 total
May 31 - Jun 1
includes taxes & fees
9.6/10 Exceptional! (385 reviews)
We had yet another wonderful stay, great views, very comfortable. Some areas (primarily outside) would benefit from some paint.
Reviewed on May 14, 2026
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
