Title: 5 Stars Hotels in Highland Beach, Annapolis from CA $154 - Find Cheap Highland Beach Hotels With 5 Stars | Expedia.ca [Highland Beach Travel Guide](https://expedia.ca/Highland-Beach.dx553248634998823058)[Hotels in Highland Beach](https://expedia.ca/Highland-Beach-Hotels.d553248634998823058.Travel-Guide-Hotels)[Vacation Rentals in Highland Beach](https://expedia.ca/Highland-Beach-Vacation-Rentals.d553248634998823058.Travel-Guide-VacationRentals)[Flights to Highland Beach](https://expedia.ca/Cheap-Flights-To-Highland-Beach.d553248634998823058.Travel-Guide-Flights)[Highland Beach Car Rentals](https://expedia.ca/Car-Rentals-In-Highland-Beach.d553248634998823058.Car-Rental-Guide)[Highland Beach Vacation Packages](https://expedia.ca/Highland-Beach.d553248634998823058.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 5 Stars Hotels in Highland Beach, Annapolis from CA $154 ![](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 Highland Beach 5 Star Hotels Tonight [Oct 24 - Oct 25](https://www.expedia.ca/Hotel-Search?regionId=553248634998823058&startDate=2025-10-24&endDate=2025-10-25&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 25 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248634998823058&startDate=2025-10-25&endDate=2025-10-26&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248634998823058&startDate=2025-10-24&endDate=2025-10-26&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248634998823058&startDate=2025-10-31&endDate=2025-11-02&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Highland Beach 5 Star Hotels ![Breakfast, lunch, dinner served; ocean views](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/38b8c334.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/3dd4d01f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/6a6b34d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/2de6ebed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Perry Cabin St. Michaels 9.6/10 Exceptional (367) "Beautiful place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ellen CA $565 CA $684 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/St-Michaels-Hotels-Inn-At-Perry-Cabin.h14576.Hotel-Information) ![Horseback riding](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/ad846553.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Romantic Studio Suite | Terrace/patio](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/ed0e25a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Suite, 1 Bedroom | Terrace/patio](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/57a2b6fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Suite, 1 Bedroom](https://images.trvl-media.com/lodging/97000000/96050000/96042500/96042430/9273007e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Tacaro Estate Tracys Landing 9.2/10 Wonderful (10) "Amazing hospitality " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gary CA $528 CA $602 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Tracys-Landing-Hotels-The-Inn-At-Tacaro-Estate.h96042430.Hotel-Information) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Highland-Beach-Hotels.s50-0-d553248634998823058.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Highland-Beach-Hotels.s50-0-d553248634998823058.Travel-Guide-Filter-Hotels) ## Explore similar 4-star hotels Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Highland Beach. ![Graduate by Hilton Annapolis](https://images.trvl-media.com/lodging/1000000/10000/900/846/dcb23c20_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Graduate by Hilton Annapolis 126 West St, Annapolis, MD CA $205 CA $234 total Nov 24 - Nov 25 includes taxes & fees 9.2/10 Wonderful! (1,015 reviews) [](https://expedia.ca/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) ![DoubleTree by Hilton Hotel Annapolis](https://images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### DoubleTree by Hilton Hotel Annapolis 210 Holiday Court, Annapolis, MD CA $135 CA $154 total Nov 18 - Nov 19 includes taxes & fees 8.6/10 Excellent! (1,019 reviews) [](https://expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![The Westin Annapolis](https://images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/w3998h2667x0y0-54f847ff_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Westin Annapolis 100 Westgate Cir, Annapolis, MD CA $222 CA $254 total Nov 23 - Nov 24 includes taxes & fees 8.6/10 Excellent! (1,005 reviews) [](https://expedia.ca/Annapolis-Hotels-The-Westin-Annapolis.h1678710.Hotel-Information) Still don't see what you're looking for? [See all properties in Highland Beach.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=25%2F10%2F2025&endDate=26%2F10%2F2025®ionId=553248634998823058&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=25%2F10%2F2025&endDate=26%2F10%2F2025®ionId=553248634998823058&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=25%2F10%2F2025&endDate=26%2F10%2F2025®ionId=553248634998823058&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=25%2F10%2F2025&endDate=26%2F10%2F2025®ionId=553248634998823058&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=25%2F10%2F2025&endDate=26%2F10%2F2025®ionId=553248634998823058&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=25%2F10%2F2025&endDate=26%2F10%2F2025®ionId=553248634998823058&star=50&star=50&amenities=WATER_PARK) 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. ## Top Highland Beach Hotel Reviews ## Find out more about Highland Beach Luxury is the name of the game at the best 5 Stars hotels in Highland Beach. If you want to vacation like a true VIP, these are the places to go; from spacious resorts to boutique-inspired hot spots, the top Highland Beach 5 Stars hotels are dedicated to immersing you in the ultimate experience. Want to relax with a serene treatment at a designer spa? These properties offer them. Interested in tasting delicious dishes from top chefs? The gourmet restaurants at the 5 Stars Highland Beach hotels have you covered. You’ll even find first-class hotels near the city’s must-see attractions and most upscale entertainment districts. Plus, when you book your trip with Expedia.ca, you’ll get access to fantastic rates and seasonal discounts, so you can take advantage of a cheap deal on 5 Stars hotels Highland Beach without giving up even an inch of quality. Everything your heart desires (and a few perks designed to make it skip a beat): That’s what’s on offer when you plan a trip to the hotels with 5 Stars in Highland Beach. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [1 Star Hotels in Holabird Industrial Park](https://www.expedia.ca/1Star-Holabird-Industrial-Park-Baltimore-Hotels.s10-n553248635976387003-0.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Cheltenham](https://www.expedia.ca/2Star-Cheltenham-Hotels.s20-0-d553248635975874284.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Graceland Park](https://www.expedia.ca/3Star-Graceland-Park-Baltimore-Hotels.s30-n553248635976385043-0.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Pleasant View Gardens](https://www.expedia.ca/3Star-Pleasant-View-Gardens-Baltimore-Hotels.s30-n553248635976385030-0.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Anchorage](https://www.expedia.ca/4Star-Anchorage-Annapolis-Hotels.s40-n553248635976473602-0.Travel-Guide-Filter-Hotels) - 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