Name: DoubleTree by Hilton Hotel Annapolis
Price range: $111 total
Rating: 8.8

Comfort Inn Largo-Washington DC East

9421 Largo Drive West Upper Marlboro MD

$93 nightly

$105 total

Jun 21 - Jun 22

Total with taxes and fees

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

8/10 Very Good! (590 reviews)

"Rooms weren’t the cleanest. But hotel accessible to all major freeways great location."

Reviewed on May 27, 2026

Historic Inns of Annapolis

58 State Circle Annapolis MD

$159 nightly

$181 total

Jun 8 - Jun 9

Total with taxes and 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! (1,860 reviews)

"There were numerous communication issues between me and the staff and managers at one point our room got up to 77° and stayed like that for hours because there was no one on staffed correct the issue although we got the historic room fee waved. I don’t believe that the staff truly cared about our ..."

Reviewed on May 28, 2026

DoubleTree by Hilton Hotel Annapolis

210 Holiday Court Annapolis MD

$98 nightly

$111 total

May 31 - Jun 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 restaurant and the ...

8.8/10 Excellent! (1,000 reviews)

"Staff was very help."

Reviewed on May 25, 2026

See all 1,275 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 coffeemaker, and in-room fireplaces. Popular attractions Romancoke Wharf County Park and Matapeake ...

9.8/10 Exceptional! (57 reviews)

"Such a cool experience"

Reviewed on May 24, 2026

NEW! Charming Farm House in Historic Kent Island

Stevensville MD

Book a stay at this golf vacation home in Stevensville. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Paul Reed Smith Guitars and Northern ...

9/10 Wonderful! (16 reviews)

Comfy stay

"comfortable for five and even the sixth person. Cute house, convenient location. Need instructions on using shower heads and on what tv channels are available."

Reviewed on Nov 3, 2022

Romantic Two Bedroom Condo

Crofton MD

Stay at this condo in Crofton. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Walden Golf Club and Regal Waugh Chapel are located ...

9.8/10 Exceptional! (104 reviews)

"Clean, quiet, welcoming space. Our host was very friendly and prompt. We’ll likely be back!"

Reviewed on May 22, 2026

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(450 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(273 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(124 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.