Madison, MD

Travel Guide

A mural of a boat with people and a quote about praying to God.
A modern building with large glass windows, a metal roof, and a small tree in the foreground.
A sculpture of a woman in a field, a quote on the wall, and a display case with a model.
A statue of a person holding a child, with a quote about family and slavery on the wall behind.
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
$162 nightly
The price is $180 total per night from Oct 8 to Oct 9
$180 total
Oct 8 - Oct 9
Total with taxes and fees
Book a stay at this business-friendly hotel in Chesapeake Beach. Enjoy an outdoor pool, 2 restaurants, and a marina. Our guests praise the helpful staff and ...
Rod 'N' Reel Resort
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street St. Michaels MD
$99 nightly
The price is $109 total per night from Oct 4 to Oct 5
$109 total
Oct 4 - Oct 5
Total with taxes and fees
Book a stay at this business-friendly hotel in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8/10 Very Good! (1,002 reviews)
"Clean and breakfast was provided. It was in the right location that we needed for our weekend. Stay."

Reviewed on Sep 30, 2026

St Michaels Inn
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd Cambridge MD
$242 nightly
The price is $275 total per night from Oct 27 to Oct 28
$275 total
Oct 27 - Oct 28
Total with taxes and fees
Book a stay at this beach resort in Cambridge. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
Hyatt Regency Chesapeake Bay
See all 573 properties in Madison
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.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Saint Michaels MD
Stay at this cottage in St. Michaels. Enjoy a garden, laundry facilities, and tennis courts. Popular attractions Muskrat Park and Higgins Yacht Yard and Marina ...
9.6/10 Exceptional! (134 reviews)
"Location was perfect and we enjoyed the sunrise every morning. Walkable to everything in St. Michael’s. Beautiful historic home and furnishings. A great stay!!"

Reviewed on Aug 24, 2026

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

St Michaels MD
Stay at this cottage in St. Michaels. Enjoy a garden, laundry facilities, and patios. Popular attractions Muskrat Park and Higgins Yacht Yard and Marina are ...
9.6/10 Exceptional! (141 reviews)
"Loved staying there and everything was so convenient!"

Reviewed on Sep 9, 2026

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Private Peninsula Estate, Pool Houses, Crab Shack

Private Peninsula Estate, Pool Houses, Crab Shack

Neavitt MD
Book a stay at this family-friendly villa in Neavitt. Enjoy private pools, a fitness center, and a garden. Popular attractions Neavitt Park and Royston Island ...
Private Peninsula Estate, Pool Houses, Crab Shack
See all properties in Madison
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.

Stay near popular Madison attractions

Harriet Tubman Underground Railroad National Historical Park

9.6/10 (95 reviews)
Learn about one of the key figures in the historic freedom of enslaved people in this park and visitor center.
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Cities near Madison

A marina with several boats docked, a building with a sign, and trees in the background.

Cambridge