Name: Graduate by Hilton Annapolis
Price range: $175 total

DoubleTree by Hilton Hotel Annapolis

210 Holiday Court Annapolis MD

$98 nightly

$111 total

Sep 27 - Sep 28

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! (1,143 reviews)

"Super friendly front staff & cleaning ladies, also extremely easy to get everything booked and checked in/out!"

Reviewed on Aug 30, 2026

Historic Inns of Annapolis

58 State Circle Annapolis MD

$147 nightly

$168 total

Sep 29 - Sep 30

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! (1,982 reviews)

"Location, cleanliness, price, friendliness of the staff. Love it there. Only place we stay when visiting Annapolis."

Reviewed on Aug 30, 2026

Graduate by Hilton Annapolis

126 West St Annapolis MD

$153 nightly

$175 total

Sep 13 - Sep 14

Total with taxes and fees

Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and ...

See all 1,295 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.

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Annapolis MD

Stay at this vacation home in Annapolis. Enjoy a fitness center, a garden, and laundry facilities. Popular attractions Sandy Point State Park and Annapolis City ...

9.8/10 Exceptional! (52 reviews)

"Great spot for extended family to get together and very convenient to downtown Annapolis. Very cute neighborhood and kids could walk to the nearby shopping center for ice cream. Rooms are lovely - everything is new and nice."

Reviewed on Aug 11, 2026

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

Rock Hall MD

Book a stay at this family-friendly villa in Rock Hall. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Rock Hall Harbor and The Mainstay ...

10/10 Exceptional! (48 reviews)

"This is a beautiful place! Spacious and very accommodating for large groups. We had 19 there and just tons of room. The grandkids loved the pool. The back yard faces the bay and provides a magnificant view for sunsets. Moreover, we were on the patio between the pool and breezeway when the feels like ..."

Reviewed on Aug 8, 2026

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 ...

7.2/10 Good! (9 reviews)

"Hands down the BEST experience I’ve had with VRBO! Kate was prompt with her communication and the boat was absolutely as she described! We are very much looking forward to going back!"

Reviewed on May 21, 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.