Name: DoubleTree by Hilton Hotel Annapolis
Price range: $69 total
Rating: 8.6

DoubleTree by Hilton Hotel Largo/Washington DC

9100 Basil Court Upper Marlboro MD

$92 nightly

$104 total

Dec 11 - Dec 12

Total with taxes and fees

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

8/10 Very Good! (1,004 reviews)

Clean room, staff was wonderful, breakfast was great, room was comfortable temp wise to sleep.

Reviewed on Nov 22, 2025

Crowne Plaza Annapolis by IHG

173 Jennifer Rd Annapolis MD

$107 nightly

$122 total

Nov 30 - Dec 1

Total with taxes and fees

Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...

8.6/10 Excellent! (1,008 reviews)

No hot shower in Suite for three days

Reviewed on Nov 19, 2025

DoubleTree by Hilton Hotel Annapolis

210 Holiday Court Annapolis MD

$61 nightly

$69 total

Dec 21 - Dec 22

Total with taxes and 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 ...

8.6/10 Excellent! (1,027 reviews)

Clean, friendly staff. Restaurant/ bar food was excellent and staff in the restaurant/ bar were fun and accommodating!

Reviewed on Nov 26, 2025

See all 1,260 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.

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Annapolis MD

Stay at this vacation home in Annapolis. Enjoy free WiFi, laundry facilities, and an in-room coffeemaker. Popular attractions Ellen O. Moyer Nature Park at Back ...

10/10 Exceptional! (32 reviews)

Excellent location and large house! Would love to stay again.

Reviewed on Nov 16, 2025

Floating 2 bed 2 bath condo stunning views of the bay

Stevensville MD

Stay at this houseboat in Stevensville. Enjoy a beach locale and an in-room coffeemaker. Popular attractions Matapeake State Park and Romancoke Wharf County ...

7/10 Good! (6 reviews)

Husband & I stayed during the Annapolis boat show to get a feel for what living on a yacht would be like for our year Great Loop adventure and to see what boat features would be important to us when buying. This stay suited us perfectly and Kate’s communication with us with very quick. A minor mechanical ...

Reviewed on Oct 8, 2025

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

Stevensville MD

Book a stay at this golf vacation home in Stevensville. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Matapeake State Park and Northern ...

9.8/10 Exceptional! (15 reviews)

The Woodland Retreat property was quiet and a good location for our fall golf trip. All beds comfortable and the place was very clean. Good hot water for showering and plenty of towels / linens. The Owner was very responsive to all questions we had prior to checkin and during our stay. The Wifi worked ...

Reviewed on Nov 14, 2025

See all 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.

Popular places to visit

U.S. Naval Academy

4.5/5(446 reviews)

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

4/5(270 reviews)

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

4.5/5(13 reviews)

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

4.5/5(123 reviews)

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.