Title: 5 Stars Hotels in Winchester, Baltimore from CA $155 - Find Cheap Winchester Hotels With 5 Stars | Expedia.ca [Winchester Travel Guide](https://expedia.ca/Baltimore-Winchester.dx553248635976395071)[Vacation Rentals in Baltimore](https://expedia.ca/Baltimore-Vacation-Rentals.d178235.Travel-Guide-VacationRentals)[Flights to Baltimore](https://expedia.ca/Cheap-Flights-To-Baltimore.d178235.Travel-Guide-Flights)[Things to do in Baltimore](https://expedia.ca/Things-To-Do-In-Baltimore.d178235.Travel-Guide-Activities)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d553248635976395071.Car-Rental-Guide)[Winchester Vacations](https://expedia.ca/Winchester.d553248635976395071.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 Winchester 5 Star Hotels Tonight [Jan 18 - Jan 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976395071&startDate=2026-01-18&endDate=2026-01-19&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 19 - Jan 20](https://www.expedia.ca/Hotel-Search?regionId=553248635976395071&startDate=2026-01-19&endDate=2026-01-20&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=553248635976395071&startDate=2026-01-23&endDate=2026-01-25&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=553248635976395071&startDate=2026-01-30&endDate=2026-02-01&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester 5-star hotels ![Couples treatment rooms, sauna, body treatments, aromatherapy](https://images.trvl-media.com/lodging/5000000/4610000/4603200/4603198/10587da6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Couples treatment rooms, sauna, body treatments, aromatherapy](https://images.trvl-media.com/lodging/5000000/4610000/4603200/4603198/fb8e3dd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 10:00 AM to 7:00 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/5000000/4610000/4603200/4603198/f16c3307.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/5000000/4610000/4603200/4603198/8ec03773.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Four Seasons Hotel Baltimore [](https://www.expedia.ca/Baltimore-Hotels-Four-Seasons-Hotel-Baltimore.h4603198.Hotel-Information) Harbor East 9.6/10 Exceptional (939 reviews) "5-Star service and the brunch was truly amazing." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jesse CA $573 CA $674 total includes taxes & fees Feb 17 - Feb 18 [](https://www.expedia.ca/Baltimore-Hotels-Four-Seasons-Hotel-Baltimore.h4603198.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/18000000/17400000/17395900/17395897/89cd8abe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/18000000/17400000/17395900/17395897/45fde7f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/18000000/17400000/17395900/17395897/a6c44038.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/18000000/17400000/17395900/17395897/e604f7ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pendry Baltimore [](https://www.expedia.ca/Baltimore-Hotels-Pendry-Baltimore.h17395897.Hotel-Information) Fells Point 9.4/10 Exceptional (1,002 reviews) "The hotel was beautiful, and the staff was courteous and friendly. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy CA $462 CA $600 total includes taxes & fees Feb 17 - Feb 18 [](https://www.expedia.ca/Baltimore-Hotels-Pendry-Baltimore.h17395897.Hotel-Information) ![Courtyard](https://images.trvl-media.com/lodging/10000000/9350000/9343300/9343273/5d60937f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/10000000/9350000/9343300/9343273/23a5b2ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/10000000/9350000/9343300/9343273/509e8b39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/10000000/9350000/9343300/9343273/6ae1d890.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Ivy Hotel [](https://www.expedia.ca/Baltimore-Hotels-The-Ivy-Hotel.h9343273.Hotel-Information) Mid-Town Belvedere 10/10 Exceptional (198 reviews) "Everything about this experience was excellent! From the valet to the concierge to the check-in person, there was a warmth and sense of pride working for and on behalf of the hotel. We have traveled the world and stayed in the best hotels, but this is by far, the best experience ever." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wonya [](https://www.expedia.ca/Baltimore-Hotels-The-Ivy-Hotel.h9343273.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-Winchester-Baltimore-Hotels.s50-n553248635976395071-0.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Winchester-Baltimore-Hotels.s50-n553248635976395071-0.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 Winchester. ![Renaissance Baltimore Harborplace Hotel](https://images.trvl-media.com/lodging/1000000/10000/10000/9973/26332e58_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Renaissance Baltimore Harborplace Hotel 202 E Pratt St Baltimore MD CA $212 CA $249 total Jan 25 - Jan 26 includes taxes & fees 8.4/10 Very Good! (2,537 reviews) [](https://expedia.ca/Baltimore-Hotels-Renaissance-Baltimore-Harborplace-Hotel.h9973.Hotel-Information) ![DoubleTree by Hilton Hotel Laurel](https://images.trvl-media.com/lodging/1000000/10000/4500/4480/2ba6a934_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### DoubleTree by Hilton Hotel Laurel 15101 Sweitzer Lane Laurel MD CA $137 CA $155 total Jan 25 - Jan 26 includes taxes & fees 8/10 Very Good! (1,000 reviews) [](https://expedia.ca/Laurel-Hotels-DoubleTree-By-Hilton-Hotel-Laurel.h4480.Hotel-Information) ![Hyatt Regency Baltimore Inner Harbor](https://images.trvl-media.com/lodging/1000000/10000/9400/9379/50c62e4f_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hyatt Regency Baltimore Inner Harbor 300 Light Street Baltimore MD CA $188 CA $221 total Feb 1 - Feb 2 includes taxes & fees 8.2/10 Very Good! (1,906 reviews) [](https://expedia.ca/Baltimore-Hotels-Hyatt-Regency-Baltimore-Inner-Harbor.h9379.Hotel-Information) Still don't see what you're looking for? [See all properties in Winchester.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=19%2F01%2F2026&endDate=20%2F01%2F2026®ionId=553248635976395071&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=19%2F01%2F2026&endDate=20%2F01%2F2026®ionId=553248635976395071&star=50&star=50&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=19%2F01%2F2026&endDate=20%2F01%2F2026®ionId=553248635976395071&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=19%2F01%2F2026&endDate=20%2F01%2F2026®ionId=553248635976395071&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=19%2F01%2F2026&endDate=20%2F01%2F2026®ionId=553248635976395071&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=19%2F01%2F2026&endDate=20%2F01%2F2026®ionId=553248635976395071&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 Winchester Hotel Reviews ![Four Seasons Hotel Baltimore](https://images.trvl-media.com/lodging/5000000/4610000/4603200/4603198/8ec03773_y.jpg) ### Four Seasons Hotel Baltimore 10/10 Excellent "We decided to stay from December 30 to January 3, and it was an amazing experience. Twice we visited the gym, and we took full advantage of the sauna. We had access to ice skating, but we sat by the fireplace and watched the young people skate. New Year's Eve was a pure delight from in-room dining to the four different restaurants with distinct cuisines. The view of the fireworks was accessible from all four dinning experiences, but The Bygone was the best location. Next year spend your holidays with the world-class staff and the best hospitality team. I hope to see you at Four Seasons Baltimore! 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