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 $1,541, price is now CA $1,350 per person
CA $1,350
per person
Jun 30 - Jul 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Salisbury (SBY)
7.6/10 Good! (525 reviews)
Could not connect to internet. Staff could've been a little friendlier/welcoming. Door to our little deck rattled constantly in the wind. Bathroom was TEENY. Toilet had to be flushed 2x to work. All in all, just a little bit run down. It was okay for an inexpensive stay; but if you're looking for 'nice', this really isn't it.
Reviewed on Apr 26, 2026
Grand Hotel Ocean City Oceanfront
Downtown Ocean City
Price was CA $2,269, price is now CA $1,944 per person
CA $1,944
per person
Jun 30 - Jul 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Salisbury (SBY)
9/10 Wonderful! (3,518 reviews)
The room was very clean, staff very helpful and there is a lot to do within the hotel itself.
Reviewed on Apr 29, 2026
Empress Motel
Downtown Ocean City
Price was CA $1,570, price is now CA $1,369 per person
CA $1,369
per person
Jun 30 - Jul 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Salisbury (SBY)
7.8/10 Good! (149 reviews)
The building is old. With that said, it was newly painted. The bathroom was clean and bright. There is a residual musty smell, but I sprayed with Lysol spray and that helped.
There was no staff in the building itself. The staff at the neighboring sister hotel was very helpful and friendly on arrival. The morning staff at departure was very tired and did not come to check me out until a second tenant arrived for his check out.
The coffee cups available in that lobby did not have caps that fit the cups on the second day I was there. That set up for a mess. The first day, the caps fit and the hot tea was greatly appreciated.
The building is so close to the beach and there was plenty of parking.
Reviewed on Apr 27, 2026
Princess Bayside Beach Hotel
Midtown Ocean City
Price was CA $1,824, price is now CA $1,613 per person
CA $1,613
per person
Jun 30 - Jul 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Salisbury (SBY)
8/10 Very Good! (1,001 reviews)
Thank you, we will be back during the summer time
Reviewed on Apr 6, 2026
Madison Hotel Deals
Rod 'N' Reel Resort
4165 Mears Ave Chesapeake Beach MD
Fully refundableReserve now, pay when you stay
The price is CA $174 per night from May 13 to May 14
CA $174
CA $221 total
May 13 - May 14
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
Had an amazing girls trip! Looking forward to my next stay.
Reviewed on Apr 29, 2026
Hyatt Regency Chesapeake Bay
100 Heron Blvd Cambridge MD
Fully refundableReserve now, pay when you stay
The price is CA $319 per night from May 18 to May 19
CA $319
CA $427 total
May 18 - May 19
includes taxes & fees
Inn at Perry Cabin
308 Watkins Ln St. Michaels MD
The price is CA $825 per night from May 6 to May 7
CA $825
CA $907 total
May 6 - May 7
includes taxes & fees
9.6/10 Exceptional! (380 reviews)
Food, drinks and staff were all awesome. They had good bikes to borrow and ride into town on if you wanted, “don’t worry about locking them, nobody will take them”. They also would drive you, and pick you up if you wanted a ride to town. Everything about the experience was 1st class. Room was very ...
Reviewed on Apr 11, 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.
