Madison Vacation Packages
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Save up to CA $1,096 when you book a flight and hotel together*
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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.
The Surf Shanty Motel
Price was CA $1,098, price is now CA $910 per person
CA $910
per person
Oct 9 - Oct 14
found 14 hours ago
Roundtrip flight included
Vancouver (YVR) to Salisbury (SBY)
9.8/10 Exceptional! (281 reviews)
Very nice and clean property. Staff was very friendly and helpful.
Reviewed on Aug. 30, 2025
Ocean Terrace Family Apartments
Downtown Ocean City
Price was CA $5,577, price is now CA $3,912 per person
CA $3,912
per person
Nov 10 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Salisbury (SBY)
8.4/10 Very Good! (29 reviews)
The unit was outdated, small, and had mismatched and old furniture. The shower in one of our bathrooms wouldn’t drain. The oven did not work. There was only one television. Concerns couldn’t be communicated because the staff hardly spoke English (although they were very nice).
The unit was in a really nice location - 1.5 blocks from the boardwalk and beach. We liked the outside showers.
Reviewed on Aug. 9, 2025
Boardwalk One
Downtown Ocean City
Price was CA $1,755, price is now CA $1,430 per person
CA $1,430
per person
Nov 10 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Salisbury (SBY)
7.2/10 Good! (161 reviews)
Directly on the Boardwalk in the heart of OC with balcony overlooking boardwalk and ocean! Friendly Staff.
Reviewed on Aug. 23, 2025
Miramar Condominiums
Downtown Ocean City
Price was CA $2,305, price is now CA $1,979 per person
CA $1,979
per person
Nov 10 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Salisbury (SBY)
9.4/10 Exceptional! (15 reviews)
Stayed in unit 505 and it was beautiful! We loved it!
Reviewed on Aug. 23, 2025
The Burgundy Inn
Downtown Ocean City
Price was CA $2,207, price is now CA $1,946 per person
CA $1,946
per person
Nov 10 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Salisbury (SBY)
6.8/10 (577 reviews)
Exactly what we needed for a mini vacay! Everyone at the front desk was helpful and personable!
Reviewed on Sep. 2, 2025
Madison Hotel Deals
Hyatt Regency Chesapeake Bay
100 Heron Blvd, Cambridge, MD
Fully refundableReserve now, pay when you stay
The price is CA $285 per night from Sep 28 to Sep 29
CA $285
CA $390 total
Sep 28 - Sep 29
includes taxes & fees
Solomons Inn Resort & Marina
155 Holiday Dr. P.O. Box 1099, Solomons, MD
Fully refundableReserve now, pay when you stay
The price is CA $172 per night from Sep 4 to Sep 5
CA $172
CA $191 total
Sep 4 - Sep 5
includes taxes & fees
St Michaels Inn
1228 S Talbot Street, St. Michaels, MD
The price is CA $123 per night from Oct 1 to Oct 2
CA $123
CA $136 total
Oct 1 - Oct 2
includes taxes & fees
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.