Title: Visit Hillsmere Shores: 2026 Travel Guide for Hillsmere Shores, Annapolis | Expedia.com [Hotels in Hillsmere Shores](https://expedia.com/Hillsmere-Shores-Hotels.d553248634998892012.Travel-Guide-Hotels)[Vacation Rentals in Hillsmere Shores](https://expedia.com/Hillsmere-Shores-Vacation-Rentals.d553248634998892012.Travel-Guide-VacationRentals)[Car Rentals in Hillsmere Shores](https://expedia.com/Car-Rentals-In-Hillsmere-Shores.d553248634998892012.Car-Rental-Guide)[Hillsmere Shores Vacation Packages](https://expedia.com/Hillsmere-Shores.d553248634998892012.Destination-Travel-Guides) # Hillsmere Shores, MD ## Travel Guide ## Visit Hillsmere Shores Things to do - Hillsmere Shores Hotel Deals - Vacation Rentals in Hillsmere Shores ![DoubleTree by Hilton Hotel Largo/Washington DC](https://images.trvl-media.com/lodging/1000000/30000/21500/21463/5fc0ae09_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### DoubleTree by Hilton Hotel Largo/Washington DC 9100 Basil Court Upper Marlboro MD $106 nightly $120 total Apr 26 - Apr 27 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 ... 8.2/10 Very Good! (1,015 reviews) I loved this property because it was in a secluded location and they allowed me to check in prior to three. the room was nice and the front desk staff were pleasant and offered me suggestions to visit the town. Reviewed on Apr 6, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F26%2F2026&endDate=4%2F27%2F2026&selected=21463&PinnedHotelID=21463&HadPinnedHotel=true®ionId=553248634998892012) ![Graduate by Hilton Annapolis](https://images.trvl-media.com/lodging/1000000/10000/900/846/ca081b22_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Graduate by Hilton Annapolis 126 West St Annapolis MD $185 nightly $211 total Apr 19 - Apr 20 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 ... 9.4/10 Exceptional! (1,004 reviews) It was the perfect location for our activities Reviewed on Apr 5, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F19%2F2026&endDate=4%2F20%2F2026&selected=846&PinnedHotelID=846&HadPinnedHotel=true®ionId=553248634998892012) ![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/e84869d1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Historic Inns of Annapolis 58 State Circle Annapolis MD $174 nightly $198 total Apr 19 - Apr 20 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! (1,870 reviews) Good location, fair price Reviewed on Apr 6, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F19%2F2026&endDate=4%2F20%2F2026&selected=42068&PinnedHotelID=42068&HadPinnedHotel=true®ionId=553248634998892012) [See all 1,267 properties in Hillsmere Shores](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=4%2F8%2F2026&endDate=4%2F9%2F2026®ionId=553248634998892012) 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](https://images.trvl-media.com/lodging/100000000/99720000/99712900/99712854/64b6a56c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### 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 ... 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 Apr 2, 2026 [](https://expedia.com/Stevensville-Hotels-Chesapeake-Houseboat-Getaway-On-Kent-Island.h99712854.Hotel-Information) ![Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres. ](https://images.trvl-media.com/lodging/102000000/101280000/101278100/101278078/4d0e4029_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### 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 ... 10/10 Exceptional! (16 reviews) This was our second time spending Thanksgiving week at Woodland Retreat. We appreciate the overall cleanliness of the house. All the beds are very comfortable. The kitchen is well stocked. The primary suite has plenty of room for baby’s portable crib. The downstairs bonus room is ideal for family ... Reviewed on Nov 30, 2025 [](https://expedia.com/Stevensville-Hotels-Woodland-Retreat-On-Kent-Island-5-Beds.h101278078.Hotel-Information) ![Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch](https://images.trvl-media.com/lodging/35000000/34590000/34583000/34582947/b1486943_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### 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 ... 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 Mar 30, 2026 [](https://expedia.com/St-Michaels-Hotels-Carpenter-St-Cottage-In-The-Heart-Of-St-Michaels-Village-Large-Screened-Porch.h34582947.Hotel-Information) [See all properties in Hillsmere Shores](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=553248634998892012&sort=VACATION_RENTAL) 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. ## Check Hillsmere Shores hotel availability [Tonight ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248634998892012&startDate=2026-04-07&endDate=2026-04-08)[Apr 7 - Apr 8](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248634998892012&startDate=2026-04-07&endDate=2026-04-08) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248634998892012&startDate=2026-04-08&endDate=2026-04-09)[Apr 8 - Apr 9](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248634998892012&startDate=2026-04-08&endDate=2026-04-09) [This weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248634998892012&startDate=4%2F10%2F2026&endDate=4%2F12%2F2026)[Apr 10 - Apr 12](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248634998892012&startDate=4%2F10%2F2026&endDate=4%2F12%2F2026) [Next weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248634998892012&startDate=4%2F17%2F2026&endDate=4%2F19%2F2026)[Apr 17 - Apr 19](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248634998892012&startDate=4%2F17%2F2026&endDate=4%2F19%2F2026) ### Popular places to visit ![U.S. Naval Academy](https://images.trvl-media.com/place/6077390/365a14c8-731b-4cc4-a5d7-9baf0c5edd8f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### U.S. Naval Academy 4.5/5(449 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. [](https://expedia.com/US-Naval-Academy-Annapolis.d6077390.Vacation-Attraction) ![Chesapeake Bay Bridge](https://images.trvl-media.com/place/6077400/4ff5201a-adee-46de-8435-a690e768b273.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 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. [](https://expedia.com/Chesapeake-Bay-Bridge-Annapolis.d6077400.Vacation-Attraction) ![Sandy Point State Park](https://images.trvl-media.com/place/6163398/25cdf98e-7f7f-4ea3-9c64-b269190b9929.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 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. [](https://expedia.com/Sandy-Point-State-Park-Annapolis.d6163398.Vacation-Attraction) ![Maryland State House](https://images.trvl-media.com/place/6077394/d18fd2cc-ea1a-41cb-8092-51a65556abb4.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 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. [](https://expedia.com/Maryland-State-House-Historic-District.d6077394.Vacation-Attraction) ![Maryland Quiet Waters Park](https://images.trvl-media.com/place/6172639/77fd279b-cba3-4e0c-8364-054b937fe279.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 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. [](https://expedia.com/Maryland-Quiet-Waters-Park-Hillsmere.d6172639.Vacation-Attraction) ![William Paca House](https://images.trvl-media.com/place/6077398/98acab84-2579-486d-a577-59008bcb9b62.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### William Paca House 4/5(16 reviews) Learn about the life and explore the historic home of 18th-century lawyer and signer of the Declaration of Independence, William Paca. [](https://expedia.com/William-Paca-House-Historic-District.d6077398.Vacation-Attraction) ### Things to do ![Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl](https://mediaim.expedia.com/localexpert/48353835/06253e20-de63-4a0a-949a-e97cb077912b.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Annapolis Ghosts: Spirits & Spirits Haunted Pub Crawl $30 per adult [](https://expedia.com/things-to-do/annapolis-ghosts-spirits-spirits-haunted-pub-crawl.a48353835.activity-details) ![Ashes and Apparitions of Annapolis Ghost Tour](https://mediaim.expedia.com/localexpert/44904461/8f8fc7ed-806b-48a3-b59a-973b562911cf.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Ashes and Apparitions of Annapolis Ghost Tour $40 per adult **100%** of travellers recommend [](https://expedia.com/things-to-do/ashes-and-apparitions-of-annapolis-ghost-tour.a44904461.activity-details) ![Historic Annapolis Food Tour](https://mediaim.expedia.com/localexpert/46405193/a95ba50e-7ba4-4054-bcbc-b797bb1a5cb7.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Historic Annapolis Food Tour $80 per adult [](https://expedia.com/things-to-do/historic-annapolis-food-tour.a46405193.activity-details) [See all activities in Hillsmere Shores](https://expedia.com/Things-To-Do-In-Hillsmere-Shores.d553248634998892012.Travel-Guide-Activities) ## Cities near Hillsmere Shores ![Annapolis](https://images.trvl-media.com/place/6034082/3328fb0e-9b35-4f86-a2cc-94c9c7b5470f.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Annapolis ![Aerial panorama view of Edgewater Maryland Almshouse Creek South River marina with luxury sail boats turquoise water, popular retirement community near Annapolis](https://images.trvl-media.com/place/6348965/5f665a73-69ac-4d51-82f8-e1866bb06ee2.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Edgewater - Cities near Hillsmere Shores - Places of interest [Annapolis](https://expedia.com/Annapolis.dx6034082)[Edgewater](https://expedia.com/Edgewater.dx6348965) - [U.S. Naval Academy ](https://expedia.com/US-Naval-Academy-Annapolis.d6077390.Vacation-Attraction) - [Chesapeake Bay ](https://expedia.com/Chesapeake-Bay-United-States-of-America.d6056980.Vacation-Attraction) - [Annapolis City Dock ](https://expedia.com/Annapolis-City-Dock-Historic-District.d553248633992240262.Vacation-Attraction) - [Westfield Annapolis Mall ](https://expedia.com/Westfield-Annapolis-Mall-Annapolis.d6172637.Vacation-Attraction) - [Chesapeake Bay Bridge ](https://expedia.com/Chesapeake-Bay-Bridge-Annapolis.d6077400.Vacation-Attraction) - [Sandy Point State Park ](https://expedia.com/Sandy-Point-State-Park-Annapolis.d6163398.Vacation-Attraction) - [Fort George G. Meade ](https://expedia.com/Fort-George-G-Meade-Baltimore.d6283177.Vacation-Attraction) - [Anne Arundel Medical Center ](https://expedia.com/Anne-Arundel-Medical-Center-Annapolis.d553248621580159030.Vacation-Attraction) - [Maryland State House ](https://expedia.com/Maryland-State-House-Historic-District.d6077394.Vacation-Attraction) - [Show Place Arena ](https://expedia.com/Show-Place-Arena-Upper-Marlboro.d6091739.Vacation-Attraction) - [Annapolis Mall Shopping Center ](https://expedia.com/Annapolis-Mall-Shopping-Center-Annapolis.d553248621563220690.Vacation-Attraction) - [Annapolis Harbor Center Shopping Center ](https://expedia.com/Annapolis-Harbor-Center-Shopping-Center-Annapolis.d553248621563220686.Vacation-Attraction) - [Bowie State University ](https://expedia.com/Bowie-State-University-Bowie.d6075472.Vacation-Attraction) - [Navy-Marine Corps Memorial Stadium ](https://expedia.com/Navy-Marine-Corps-Memorial-Stadium-Annapolis.d6091645.Vacation-Attraction) - [Northern Chesapeake Bay ](https://expedia.com/Northern-Chesapeake-Bay-Maryland.d6051456.Vacation-Attraction) - [Maryland Quiet Waters Park ](https://expedia.com/Maryland-Quiet-Waters-Park-Hillsmere.d6172639.Vacation-Attraction) - [Chesapeake Bay Maritime Museum ](https://expedia.com/Chesapeake-Bay-Maritime-Museum-Downtown-St-Michaels.d553248633992441010.Vacation-Attraction) - [St. Michaels Winery ](https://expedia.com/St-Michaels-Winery-Downtown-St-Michaels.d553248633992438808.Vacation-Attraction) - [Queenstown Harbor Golf ](https://expedia.com/Queenstown-Harbor-Golf-Club-Queenstown.d6091731.Vacation-Attraction) - [Prince George's Stadium ](https://expedia.com/Prince-Georges-Stadium-Bowie.d553248621558141357.Vacation-Attraction) - [William Paca House ](https://expedia.com/William-Paca-House-Historic-District.d6077398.Vacation-Attraction) - [Annapolis Maritime Museum ](https://expedia.com/Annapolis-Maritime-Museum-Eastport.d553248621532662325.Vacation-Attraction) - [Maryland Hall for Creative Arts ](https://expedia.com/Maryland-Hall-For-Creative-Arts-Annapolis.d553248621580159031.Vacation-Attraction) - [Rock Hall Harbor ](https://expedia.com/Rock-Hall-Harbor-Rock-Hall.d553248621561173703.Vacation-Attraction) - [Rod n Reel Charter Fishing ](https://expedia.com/Rod-N-Reel-Charter-Fishing-Chesapeake-Beach.d553248621561879529.Vacation-Attraction) - [Annapolis Harbour Center ](https://expedia.com/Annapolis-Harbour-Center-Edgewater.d553248621561879652.Vacation-Attraction) - [Chesapeake Beach Water Park ](https://expedia.com/Chesapeake-Beach-Water-Park-Chesapeake-Beach.d553248621532662257.Vacation-Attraction) - [Prince George's Community College ](https://expedia.com/Prince-Georges-Community-College-Upper-Marlboro.d6283667.Vacation-Attraction) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save even more - get up to 20% on select hotels when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. 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