Title: 5 Stars Hotels in Westernport, Maryland - Find Cheap Westernport Hotels With 5 Stars | Expedia.ca [Westernport Travel Guide](https://expedia.ca/Westernport.dx3000440935)[Hotels in Westernport](https://expedia.ca/Westernport-Hotels.d3000440935.Travel-Guide-Hotels)[Vacation Rentals in Westernport](https://expedia.ca/Westernport-Vacation-Rentals.d3000440935.Travel-Guide-VacationRentals)[Flights to Westernport](https://expedia.ca/Cheap-Flights-To-Westernport.d3000440935.Travel-Guide-Flights)[Westernport Car Rentals](https://expedia.ca/Car-Rentals-In-Westernport.d3000440935.Car-Rental-Guide)[Westernport Vacation Packages](https://expedia.ca/Westernport.d3000440935.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/0a8402d1abbf8e4aa56c2fb4c50438ca.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Shelly Sisler # 5 Stars Hotels in Westernport, Maryland ![](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 Westernport 5 Star Hotels Tonight [Oct 21 - Oct 22](https://www.expedia.ca/Hotel-Search?regionId=3000440935&startDate=2025-10-21&endDate=2025-10-22&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 22 - Oct 23](https://www.expedia.ca/Hotel-Search?regionId=3000440935&startDate=2025-10-22&endDate=2025-10-23&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=3000440935&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=3000440935&startDate=2025-10-31&endDate=2025-11-02&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Westernport 5 Star Hotels ![Exterior](https://images.trvl-media.com/lodging/33000000/32730000/32721100/32721047/1a59f6a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, Multiple Beds, Hot Tub | Private kitchen](https://images.trvl-media.com/lodging/33000000/32730000/32721100/32721047/183017ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, Multiple Beds, Hot Tub | Bathroom](https://images.trvl-media.com/lodging/33000000/32730000/32721100/32721047/3215a99f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, Multiple Beds, Hot Tub | Bathroom](https://images.trvl-media.com/lodging/33000000/32730000/32721100/32721047/84d2b3fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Preston on the Lake 5 Bedroom House Oakland [](https://www.expedia.ca/Cumberland-Hotels-Preston-On-The-Lake-5-Bedroom-House.h32721047.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-Westernport-Hotels.s50-0-d3000440935.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Westernport-Hotels.s50-0-d3000440935.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 Westernport. ![Loft of Luxury](https://images.trvl-media.com/lodging/78000000/77820000/77817200/77817107/91474100_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Loft of Luxury Oakland [Get rates](https://expedia.ca/Hotel-Search?startDate=05%2F11%2F2025&endDate=06%2F11%2F2025&selected=77817107&PinnedHotelID=77817107&HadPinnedHotel=true®ionId=3000440935) [](https://expedia.ca/Oakland-Hotels-Loft-Of-Luxury.h77817107.Hotel-Information) ![Bear Hollow Lodge](https://images.trvl-media.com/lodging/76000000/75980000/75970300/75970245/a709d25a_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Bear Hollow Lodge 20590 GARRETT HWY, Oakland, MD [Get rates](https://expedia.ca/Hotel-Search?startDate=05%2F11%2F2025&endDate=06%2F11%2F2025&selected=75970245&PinnedHotelID=75970245&HadPinnedHotel=true®ionId=3000440935) [](https://expedia.ca/Oakland-Hotels-Bear-Hollow-Lodge.h75970245.Hotel-Information) ![Tranquility](https://images.trvl-media.com/lodging/77000000/76020000/76011700/76011676/0d465b2a_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Tranquility 285 CHERRY HEIGHTS LN, McHenry, MD [Get rates](https://expedia.ca/Hotel-Search?startDate=05%2F11%2F2025&endDate=06%2F11%2F2025&selected=76011676&PinnedHotelID=76011676&HadPinnedHotel=true®ionId=3000440935) [](https://expedia.ca/McHenry-Hotels-Tranquility.h76011676.Hotel-Information) Still don't see what you're looking for? [See all properties in Westernport.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=23%2F10%2F2025&endDate=24%2F10%2F2025®ionId=3000440935&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=23%2F10%2F2025&endDate=24%2F10%2F2025®ionId=3000440935&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=23%2F10%2F2025&endDate=24%2F10%2F2025®ionId=3000440935&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=23%2F10%2F2025&endDate=24%2F10%2F2025®ionId=3000440935&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=23%2F10%2F2025&endDate=24%2F10%2F2025®ionId=3000440935&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=23%2F10%2F2025&endDate=24%2F10%2F2025®ionId=3000440935&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. ## Learn more about Westernport Venture to sights like Savage River as you discover the local area in Westernport. [See all hotels in Westernport](https://www.expedia.ca/Hotel-Search?startDate=2025-11-05&endDate=2025-11-06&adults=2®ionId=3000440935) ![](https://mediaim.expedia.com/destination/2/0a8402d1abbf8e4aa56c2fb4c50438ca.jpg?impolicy=fcrop&w=225&h=400&p=1&q=high) Photo by Shelly Sisler ## Top Westernport Hotel Reviews ## Find out more about Westernport Luxury is the name of the game at the best 5 Stars hotels in Westernport. 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 Westernport 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 Westernport 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 Westernport 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 Westernport. ## Frequently asked questions ### How much does it cost to stay in a 5-star hotel in Westernport? > The amount you pay for a 5-star hotel in Westernport can vary according to what time of year you travel and how long you plan to stay, among other factors. Take advantage of our price per night filter and other search tools to score the best rate on a high-end stay. > > > > - Search for the lowest price per night ### What makes a hotel 5 stars in Westernport? > In Westernport, a hotel needs to offer a certain amount of upscale features to be rated 5 stars. These may include on-site gyms, spas and saunas, gourmet restaurants, premium bedding, luxury bathroom products and more. What also sets 5-star hotels apart is their guest-focused service. You can look forward to things like nightly turn-down services, in-room massages and concierge services. Some may also offer additional touches like a welcome gift. ### Are there any 5-star all-inclusive resorts in Westernport? > Use Expedia's filters to find an upmarket getaway in Westernport where everything you need is included. Next, narrow your results for properties that have a rating of 5 stars and are deemed "All inclusive." The most important thing on the agenda at these stays? 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