Name: Historic Inns of Annapolis
Price range: €155
Rating: 9

DoubleTree by Hilton Hotel Largo/Washington DC

9100 Basil Court Upper Marlboro MD

€102

26 Apr - 27 Apr

includes taxes & fees

Stay at this business-friendly hotel in Upper Marlboro. Enjoy free parking, breakfast (surcharge) and a 24-hour fitness centre. Popular attractions Northwest ...

8.2/10 Very Good! (1,007 reviews)

Everything was clean, the staff was friendly and the esthetics were pleasant.

Reviewed on 11 Apr 2026

Graduate by Hilton Annapolis

126 West St Annapolis MD

€183

3 May - 4 May

includes taxes & fees

Stay at this business-friendly hotel in Annapolis. Enjoy free Wi-Fi, breakfast (surcharge) and a 24-hour fitness centre. Our guests praise the bar and the helpful ...

9.4/10 Exceptional! (1,010 reviews)

Outstanding

Reviewed on 11 Apr 2026

Historic Inns of Annapolis

58 State Circle Annapolis MD

€155

19 Apr - 20 Apr

includes taxes & fees

Stay at this historic hotel in Annapolis. Enjoy free Wi-Fi, room service and a 24-hour fitness centre. Our guests praise the helpful staff and the clean rooms ...

9/10 Wonderful! (1,874 reviews)

Valet parking is available. I received a bottle of wine as a gift, wow! The room is spacious but dark, there is no window to the outdoors. The window overlooks a closed-in courtyard that looks as it serves as events (weddings?) venue.

Reviewed on 11 Apr 2026

See all 1,267 properties in Hillsmere Shores

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.

Chesapeake Houseboat Getaway on Kent Island, Maryland

Stevensville MD

Stay at this houseboat in Stevensville. Enjoy patios, an in-room coffee maker and in-room fireplaces. Popular attractions Romancoke Wharf County Park and Matapeake ...

10/10 Exceptional! (51 reviews)

The houseboat was an absolute dream. We loved everything about it and really enjoyed our two night stay. Julia has thought of everything to make your stay comfortable. It was immaculate, well stocked and all the decor was beautiful. We would love to come back.

Reviewed on 2 Apr 2026

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

Stevensville MD

Stay at this golf holiday home in Stevensville. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Matapeake State Park and Northern Chesapeake ...

10/10 Exceptional! (17 reviews)

It’s beautiful place inside and out!

Reviewed on 8 Apr 2026

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Saint 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 located ...

9.8/10 Exceptional! (200 reviews)

A lovely home just a block from the shops and restaurants on Talbot Street. The rear addition adds generous living space while preserving the charm of the historic house. The screened-in back deck is a great feature for relaxing evenings.Upstairs, the bedroom feels like a second retreat—spacious, ...

Reviewed on 30 Mar 2026

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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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Popular places to visit

U.S. Naval Academy

See where future generations of Navy and Marine Corps officers are trained at this historic federal service academy within a former fort in Annapolis harbor.

Chesapeake Bay Bridge

Attempt the nerve-racking drive across this long and notoriously scary bridge, which provides fabulous views of Chesapeake Bay for passengers.

Sandy Point State Park

Sunbathe on the beach, enjoy unrivaled views of the Chesapeake Bay Bridge and go hiking, swimming, fishing and boating in this vast park.

Maryland State House

Appreciate the superb architecture and fascinating history of America’s first peacetime capitol and the oldest state capitol still in legislative use.

Maryland Quiet Waters Park

Stroll along miles of trails through grassy parkland, hardwood forests and riverfront promenades and check out the visitor center at this pretty park.