Madison, MD
Travel Guide
Visit Madison
Hyatt Regency Chesapeake Bay
100 Heron Blvd Cambridge MD
$285 nightly
The price is $324 total per night from Jun 1 to Jun 2
$324 total
Jun 1 - Jun 2
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. ...
8.8/10 Excellent! (1,002 reviews)
"Hotel is beautiful , grounds are beautiful ! Staff is amazing ! Only disappointment was the pool situation - Seems like if you are there during the week or if weather isn’t perfect restaurants and amenities aren’t available as expected. It wasn’t raining just overcast, and it was warm and humid out ..."
Reviewed on May 27, 2026
Rod 'N' Reel Resort
4165 Mears Ave Chesapeake Beach MD
Fully refundable
$187 nightly
The price is $204 total per night from Jun 18 to Jun 19
$204 total
Jun 18 - Jun 19
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 ...
8.6/10 Excellent! (1,002 reviews)
"Beautiful hotel. We stayed a couple days for a wedding in the area. We had a beautiful deck with a beautiful view. We were in 227. The area was great for walks. The staff was friendly and helpful."
Reviewed on May 27, 2026
Inn at Perry Cabin
308 Watkins Ln St. Michaels MD
$621 nightly
The price is $683 total per night from May 31 to Jun 1
$683 total
May 31 - Jun 1
Total with taxes and fees
Book a stay at this luxury hotel in St. Michaels. Enjoy free WiFi, free valet parking, and a full-service spa. Our guests praise the helpful staff in our reviews. ...
9.6/10 Exceptional! (387 reviews)
"We enjoyed a wonderful, stress-free four days at the inn and the surrounding area. Highly recommend it."
Reviewed on May 22, 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.
Soul Oasis - home on the Chesapeake Bay
Lusby MD
Stay at this cottage in Lusby. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Drum Point Lake and Cove Point Beach are located nearby.
10/10 Exceptional! (49 reviews)
"Soul Oasis is a lovely property for a couple's getaway."
Reviewed on May 22, 2026
Relaxing Waterfront Cottage Near St Michaels, Maryland
Wittman MD
Stay at this cottage in Wittman. Enjoy free WiFi, private pools, and laundry facilities. Our guests praise the property condition in our reviews. Popular attractions ...
9.8/10 Exceptional! (244 reviews)
"We thoroughly enjoyed our stay! The Maghee House was bright, well appointed, up-to-date and very comfortable. We rented the home because it was on the water and had a nice dock to launch our kayaks. The area on Harris Creek was beautiful for kayaking. It would have been nice to have some empty cabinet ..."
Reviewed on May 12, 2026
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Cambridge MD
Stay at this vacation home in Cambridge. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Ragged Island and Spocott Windmill are located ...
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.
Popular places to visit
Harriet Tubman Underground Railroad National Historical Park
4.5/5(14 reviews)
Learn about one of the key figures in the historic freedom of enslaved people in this park and visitor center.
- Chesapeake Bay
- Patuxent River Naval Air Station
- Breezy Point Beach
- Blackwater National Wildlife Refuge
- Calvert Cliffs State Park
- Chesapeake Bay Maritime Museum
- Gerry Boyle Park at Great Marsh
- Northern Chesapeake Bay
- Chesapeake Beach Water Park
- Harriet Tubman Museum and Educational Center
- Rod n Reel Charter Fishing
- Choptank River Lighthouse
- St. Michaels Winery
- Harriet Tubman Underground Railroad National Historical Park
- Avalon Theatre
- Cove Point Lighthouse
- Talbot County Visitor Center
- Running Hare Vineyard
- Long Wharf Park
- Layton's Chance Vineyard and Winery
- Jefferson Patterson Park and Museum
- Chesapeake Beach Railway Museum
- Drum Point Lighthouse
- Dorchester County Visitors Center
