Madison Holidays

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The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

Madison Holiday

Our pick of the best 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 NZ$396 per night from 15 Mar to 16 Mar
NZ$396
15 Mar - 16 Mar
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
Nice stay, but a little too crowded.

Reviewed on 30 Jan 2026

Hyatt Regency Chesapeake Bay
Rod 'N' Reel Resort

Rod 'N' Reel Resort

4 out of 5
4165 Mears Ave Chesapeake Beach MD
Fully refundableReserve now, pay when you stay
The price is NZ$215 per night from 19 Feb to 20 Feb
NZ$215
19 Feb - 20 Feb
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
Newly remodeled rooms. Very clean. Staff was so friendly and courteous! I love the fact there are two restaurants on site.

Reviewed on 9 Feb 2026

Rod 'N' Reel Resort
The Tidewater Inn

The Tidewater Inn

3 out of 5
101 E Dover St Easton MD
The price is NZ$326 per night from 15 Mar to 16 Mar
NZ$326
15 Mar - 16 Mar
includes taxes & fees
8.8/10 Excellent! (848 reviews)
Beautiful historic but with nice mix-in of modern hotel. Friendly, professional staff. Great location. My wife and I had a fantastic stay.

Reviewed on 13 Jan 2026

The Tidewater Inn
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.