Madison Holidays
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Top hotels in Madison
Hyatt Regency Chesapeake Bay
100 Heron Blvd Cambridge MD
Fully refundableReserve now, pay when you stay
The price is S$287 per night from 1 Jan to 2 Jan
S$287
1 Jan - 2 Jan, 2026
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
Enjoyed everything about my one night stay. The staff was very hospitable and accommodating. The room was awesome with a very nice view of the surrounding water. Overall, a very positive experience.
Reviewed on 5 Dec, 2025
Rod 'N' Reel Resort
4165 Mears Ave Chesapeake Beach MD
Fully refundableReserve now, pay when you stay
The price is S$155 per night from 2 Jan to 3 Jan
S$155
2 Jan - 3 Jan, 2026
includes taxes & fees
8.2/10 Very Good! (1,002 reviews)
Room was nice, except for the heating system, which was noisy and seemed to blow cool air
Reviewed on 13 Dec, 2025
Inn at Perry Cabin
308 Watkins Ln St. Michaels MD
The price is S$811 per night from 30 Dec to 31 Dec
S$811
30 Dec - 31 Dec
includes taxes & fees
9.4/10 Exceptional! (371 reviews)
Fantastic resort; beautiful with lots of great history. Highly recommend the historic walking tour with Jay.
Reviewed on 12 Nov, 2025
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
