Title: Book the Best BEACH RESORTS in Hillsmere, Annapolis - Hillsmere Hotels on the Beach| Expedia.ca [Vacation Rentals in Annapolis](https://expedia.ca/Annapolis-Vacation-Rentals.d6034082.Travel-Guide-VacationRentals)[Flights to Annapolis](https://expedia.ca/Cheap-Flights-To-Annapolis.d6034082.Travel-Guide-Flights)[Things to do in Annapolis](https://expedia.ca/Things-To-Do-In-Annapolis.d6034082.Travel-Guide-Activities)[Hillsmere Car Rentals](https://expedia.ca/Car-Rentals-In-Hillsmere.d553248635976473205.Car-Rental-Guide)[Hillsmere Vacations](https://expedia.ca/Hillsmere.d553248635976473205.Destination-Travel-Guides) ![Chesapeake Bay Bridge with blue and orange sunset](https://images.trvl-media.com/place/553248635976473205/28fdb621-ca24-4585-bcbf-a8fecaccb105.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Beach Hotel in Hillsmere, Annapolis - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Hillsmere Beach Hotel Tonight [Nov 30 - Dec 1](https://www.expedia.ca/Hotel-Search?regionId=553248635976473205&startDate=2025-11-30&endDate=2025-12-01&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach) Tomorrow [Dec 1 - Dec 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976473205&startDate=2025-12-01&endDate=2025-12-02&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach) Next weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=553248635976473205&startDate=2025-12-05&endDate=2025-12-07&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach) In two weeks [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248635976473205&startDate=2025-12-12&endDate=2025-12-14&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach) ## Top Hillsmere Beach Hotel ![Interior](https://images.trvl-media.com/lodging/84000000/83600000/83593300/83593218/2f9aa4ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/84000000/83600000/83593300/83593218/ddc35931.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83600000/83593300/83593218/1e4bb30c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/84000000/83600000/83593300/83593218/afd24f81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Black Friday: Get 10% Off Holiday Stays Hillsmere 9.8/10 Exceptional (32) "Perfect place for a family long weekend getaway! Very relaxing location, clean, comfortable, and beautiful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Valentina S. [](https://www.expedia.ca/Annapolis-Hotels-Serene-Sunsets-At-Historic-Waterfront-Home.h83593218.Hotel-Information) ![Children's area](https://images.trvl-media.com/lodging/120000000/119550000/119541300/119541247/735298b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119550000/119541300/119541247/16f0980f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119550000/119541300/119541247/82951545.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/120000000/119550000/119541300/119541247/a427b24f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New! Quiet Waters Family Home 4BR Sleeps 8 Hillsmere [](https://www.expedia.ca/Annapolis-Hotels-Quiet-Waters-Family-Home-4BR-Sleeps-8.h119541247.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/84000000/83610000/83607100/83607100/12890450.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/84000000/83610000/83607100/83607100/76684711.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/84000000/83610000/83607100/83607100/d635f67d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/84000000/83610000/83607100/83607100/ac75c15e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Easy Annapolis lodging - still available for Sailboat Show! Hillsmere [](https://www.expedia.ca/Annapolis-Hotels-Easy-Annapolis-Lodging-Still-Available-For-Sailboat-Show.h83607100.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-14&endDate=2025-12-15®ionId=553248635976473205&adults=2&travelerType=beach&sort=RECOMMENDED&openPlayBack=true) ## Top Hillsmere Hotel Reviews ![Graduate by Hilton Annapolis](https://images.trvl-media.com/lodging/1000000/10000/900/846/dcb23c20_y.jpg) ### Graduate by Hilton Annapolis 10/10 Excellent "Clean older rooms. Quite comfortable. Rick at the front desk was a superstar! Knowledgeable, and friendly. Great example for the younger staff. " [](https://expedia.ca/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) ## Frequently asked questions ### What is Hillsmere like for travelers who love the beach? > Find a great place to stay in Hillsmere, which has a lot to offer the traveler looking to book a beach vacation. ### What is there to see and do around Hillsmere? > After arriving and settling in at your hotel, you might want to venture out and explore everything Hillsmere has to offer. If you're eager to check out the beaches, head to Bay Ridge Beach or Sandy Point Beach for some relaxation by the water. Make time for a range of local attractions, which include Maryland Quiet Waters Park and Great Frogs Winery. 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