Deale

Travel Guide

An aerial view of a beach with clear water, a sandy shore, and visible footprints.
Scenic aerial panorama of Deale waterfront fishing village on the Western Shore of Chesapeake Bay Maryland, popular with boaters. Four tidal creeks Rockhold, Broadwater, Carrs , Parker flow into bay
Marina Deale MD near Chesapeake Bay
Scenic aerial panorama of Deale waterfront docks on the Western Shore of Chesapeake Bay Maryland, dozens of luxury sailboats docking in the marina.
Aerial panorama of Deale waterfront docks on the Western Shore of Chesapeake Bay Maryland, with rows of of luxury sailboats docking in the marina.
Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina

2.5 out of 5
604 Cabana Blvd Deale MD
Fully refundableReserve now, pay when you stay
The price is CA $315 per night from Jun 30 to Jul 1
CA $315
CA $359 total
Jun 30 - Jul 1
includes taxes & fees
Book a stay at this business-friendly hotel in Deale. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
9.4/10 Exceptional! (489 reviews)
"Everything is amazing the view and the vibes. Disclaimer the balcony by the marina you will not be able to sit on there at night there is so many mosquitoes"

Reviewed on Jun 21, 2026

Anchored Inn at Hidden Harbour Marina
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle Annapolis MD
The price is CA $128 per night from Jul 1 to Jul 2
CA $128
CA $194 total
Jul 1 - Jul 2
includes taxes & fees
Book a stay at this historic hotel in Annapolis. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,865 reviews)
"At first we were placed in the Calvert House but then switched to the Johnson. The shower plumbing was broken. The shower soap pump did not work. The tub porcelain was chipped and the pillows were very hard. The door did not seal at the bottom and hall light came in. Air conditioning was noisy. I ..."

Reviewed on Jun 22, 2026

Historic Inns of Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
The price is CA $157 per night from Jul 2 to Jul 3
CA $157
CA $179 total
Jul 2 - Jul 3
includes taxes & fees
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the ...
DoubleTree by Hilton Hotel Annapolis
See all 1,229 properties in Deale
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.
Million Dollar View of the Chesapeake Bay

Million Dollar View of the Chesapeake Bay

Deale MD
Book a stay at this family-friendly vacation home in Deale. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Upper Yough River and Franklin ...
9.8/10 Exceptional! (137 reviews)
"We stayed at this beautiful waterfront property to celebrate my dad’s 90th birthday, and it could not have been a more memorable experience. The setting is absolutely breathtaking, with stunning waterfront views and a peaceful, quiet atmosphere that made it easy to relax and enjoy time with family.The ..."

Reviewed on Jun 21, 2026

Million Dollar View of the Chesapeake Bay
Firefly Cottage at the Cape, Hot Tub, Community beach, summer fun, USNA visits.

Firefly Cottage at the Cape, Hot Tub, Community beach, summer fun, USNA visits.

Annapolis MD
Stay at this cottage in Annapolis. Enjoy free breakfast, free WiFi, and a garden. Popular attractions Annapolis City Dock and Sandy Point State Park are located ...
10/10 Exceptional! (110 reviews)
"We had a wonderful three-night stay and couldn’t have been more pleased with both the property and the host. The cottage was exceptionally comfortable, relaxing, spotless, and very dog-friendly. It provided the perfect place to unwind while visiting family.We did experience a power outage during ..."

Reviewed on Jun 14, 2026

Firefly Cottage at the Cape, Hot Tub, Community beach, summer fun, USNA visits.
Grace Cottage, St Michaels Walk to everything!

Grace Cottage, St Michaels Walk to everything!

Saint Michaels MD
Stay at this vacation home in St. Michaels. Enjoy laundry facilities, in-room fireplaces, and air conditioning. Popular attractions Saint Marys Square and Saint ...
10/10 Exceptional! (6 reviews)
"We had such a wonderful time staying at Grace Cottage. Lisa, the hostes, was very responsive and very, very kind. The cottage was right in the middle of all shopping and restaurants. It is beautifully decorated and is totally stocked with everything you would need. Thank you so much Lisa for making ..."

Reviewed on May 8, 2026

Grace Cottage, St Michaels Walk to everything!
See all properties in Deale
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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