Title: Book the Best HISTORIC Hotels in Winter Park in 2026 | Expedia.ca [Hotels in Winter Park](https://expedia.ca/Winter-Park-Hotels.d7902.Travel-Guide-Hotels)[Vacation Rentals in Winter Park](https://expedia.ca/Winter-Park-Vacation-Rentals.d7902.Travel-Guide-VacationRentals)[Flights to Winter Park](https://expedia.ca/Cheap-Flights-To-Winter-Park.d7902.Travel-Guide-Flights)[Winter Park Car Rentals](https://expedia.ca/Car-Rentals-In-Winter-Park.d7902.Car-Rental-Guide)[Winter Park Vacation Packages](https://expedia.ca/Winter-Park.d7902.Destination-Travel-Guides) ![Kraft Azalea Gardens showing a fountain, a park and a pond](https://images.trvl-media.com/place/553248621532654339/aef9d03a-cd86-4dcc-8e9d-049aef598da5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Historic Hotels in Winter Park, FL from CA $124 - ![](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 Winter Park Historic Hotels Tonight [Dec 25 - Dec 26](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2025-12-25&endDate=2025-12-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 26 - Dec 27](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2025-12-26&endDate=2025-12-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=7902&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winter Park historic hotels ![Front of property](https://images.trvl-media.com/lodging/2000000/1790000/1784900/1784873/21834885.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front Side Balcony Suite, 1 King](https://images.trvl-media.com/lodging/2000000/1790000/1784900/1784873/96b386a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/2000000/1790000/1784900/1784873/450d6e5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1790000/1784900/1784873/52e0ae75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Park Plaza Hotel [](https://www.expedia.ca/Orlando-Hotels-Park-Plaza-Hotel.h1784873.Hotel-Information) Park Avenue District 8.6/10 Excellent (1000) "Would stay at the Park again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Edward CA $230 CA $259 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Orlando-Hotels-Park-Plaza-Hotel.h1784873.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/18700/18667/dc1f4aa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/1000000/20000/18700/18667/a5c22010.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/18700/18667/41313b63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/1000000/20000/18700/18667/418ef992.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DASKK Orlando Hotel near Universal Blvd, an Ascend Collection Hotel [](https://www.expedia.ca/Orlando-Hotels-Quality-Suites-Orlando-Convention-Center-Area.h18667.Hotel-Information) International Drive District 8.6/10 Excellent (740) "What a wonderful stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lucia CA $121 CA $136 total includes taxes & fees Jan 25 - Jan 26, 2026 [](https://www.expedia.ca/Orlando-Hotels-Quality-Suites-Orlando-Convention-Center-Area.h18667.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/4000/3916/55b45a9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/4000/3916/575efd8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor wedding](https://images.trvl-media.com/lodging/1000000/10000/4000/3916/d5745363.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/4000/3916/1fbd324f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wyndham I-Drive Avanti Resort & Conference Center [](https://www.expedia.ca/Orlando-Hotels-Avanti-Palms-Resort-And-Conference-Center.h3916.Hotel-Information) International Drive District 7.4/10 Good (3924) "Excellent room and the beds were very comfortable, also very clean " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daisy CA $85 CA $124 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Orlando-Hotels-Avanti-Palms-Resort-And-Conference-Center.h3916.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/20000/11400/11308/9b318259.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 outdoor pools, open 9:00 AM to 10:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/11400/11308/w1522h1017x0y0-5ae34fdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Buffet](https://images.trvl-media.com/lodging/1000000/20000/11400/11308/099409e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/1000000/20000/11400/11308/72d227b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rosen Inn International [](https://www.expedia.ca/Orlando-Hotels-Rosen-Inn-International.h11308.Hotel-Information) International Drive District 8.4/10 Very good (5880) "Room very cleaned and great staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anibal CA $121 CA $136 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Orlando-Hotels-Rosen-Inn-International.h11308.Hotel-Information) ![Mini-fridge, microwave, cookware/dishes/utensils](https://images.trvl-media.com/lodging/100000000/99360000/99355200/99355180/6fecb2d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99360000/99355200/99355180/51d1bee4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/100000000/99360000/99355200/99355180/c6a2da7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/100000000/99360000/99355200/99355180/2cc09827.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bella Breeze [](https://www.expedia.ca/Sanford-Hotels-Bella-Breeze.h99355180.Hotel-Information) Sanford 9.6/10 Exceptional (5) "The place was clean, cozy, and well decorated, and the amenities were wonderful! The hosts have done a great job here." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Courteny [](https://www.expedia.ca/Sanford-Hotels-Bella-Breeze.h99355180.Hotel-Information) ![Fridge, microwave, oven, dishwasher](https://images.trvl-media.com/lodging/101000000/100960000/100956000/100955919/11af10e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/101000000/100960000/100956000/100955919/90310fe7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/101000000/100960000/100956000/100955919/39fc93e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/101000000/100960000/100956000/100955919/f22c7c23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sanford's Seahaven: fully fenced yard, outdoor dining, close to downtown! [](https://www.expedia.ca/Sanford-Hotels-Sanfords-Seahaven.h100955919.Hotel-Information) Sanford 10/10 Exceptional (3) "We had a wonderful time. The town, house and weather were perfect." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anne T. CA $378 CA $642 total includes taxes & fees Jan 19 - Jan 20, 2026 [](https://www.expedia.ca/Sanford-Hotels-Sanfords-Seahaven.h100955919.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/36000000/35740000/35738700/35738680/4a5ba30d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/36000000/35740000/35738700/35738680/43726a23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/36000000/35740000/35738700/35738680/1f721d78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/36000000/35740000/35738700/35738680/3a229cea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mills Cottage by the Little Lake [](https://www.expedia.ca/Orlando-Hotels-Mills-Cottage-On-Small-Lake.h35738680.Hotel-Information) Lake Weldona 10/10 Exceptional (49) "Beautiful property with excellent amenities. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alexis E. CA $202 CA $474 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Orlando-Hotels-Mills-Cottage-On-Small-Lake.h35738680.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/50000000/49240000/49237900/49237899/7b92f5af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/50000000/49240000/49237900/49237899/aa70a5c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/50000000/49240000/49237900/49237899/16f3fb0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/50000000/49240000/49237900/49237899/05cfd8ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lake House Pets allowed [](https://www.expedia.ca/Orlando-Hotels-Lake-House-Pets-Allowed.h49237899.Hotel-Information) Lake Weldona 9.8/10 Exceptional (52) "This property is a hidden oasis! Absolutely magical in every way. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy G. [](https://www.expedia.ca/Orlando-Hotels-Lake-House-Pets-Allowed.h49237899.Hotel-Information) ![Lounge](https://images.trvl-media.com/lodging/60000000/59300000/59293900/59293823/a245dc4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/60000000/59300000/59293900/59293823/58d1548b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/60000000/59300000/59293900/59293823/4f3a4f09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/60000000/59300000/59293900/59293823/dc1109ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### AC Hotel by Marriott Orlando Downtown [](https://www.expedia.ca/Orlando-Hotels-AC-Hotel-By-Marriott-Orlando-Downtown.h59293823.Hotel-Information) Downtown Orlando 9.2/10 Wonderful (1055) "This is a nice property and we loved the Sky Bar. Very nice and convenient to the arena. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven CA $245 CA $275 total includes taxes & fees Jan 2 - Jan 3, 2026 [](https://www.expedia.ca/Orlando-Hotels-AC-Hotel-By-Marriott-Orlando-Downtown.h59293823.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/50000000/49260000/49256800/49256791/81d01ab7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/50000000/49260000/49256800/49256791/4e79313f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/50000000/49260000/49256800/49256791/eb562748.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/50000000/49260000/49256800/49256791/c8e87344.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Large, beautiful, very comfortable one bedroom on small lake [](https://www.expedia.ca/Orlando-Hotels-Cute-One-Bedroom-On-Small-Lake.h49256791.Hotel-Information) Lake Weldona 10/10 Exceptional (59) "Our 2 night stay was wonderful! A beautiful place to enjoy and relax. We will definitely being staying here again when we are in Orlando." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jolyn W. CA $202 CA $414 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Orlando-Hotels-Cute-One-Bedroom-On-Small-Lake.h49256791.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=2026-01-08&endDate=2026-01-09®ionId=7902&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Winter Park Hotel Reviews ![Caribe Royale Orlando](https://images.trvl-media.com/lodging/1000000/50000/40900/40865/033f2fa5_y.jpg) ### Caribe Royale Orlando 10/10 Excellent "Yes" [](https://expedia.ca/Orlando-Hotels-Caribe-Royale-Orlando.h40865.Hotel-Information) ![Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando](https://images.trvl-media.com/lodging/1000000/30000/23200/23110/ade3b60d_y.jpg) ### Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando 10/10 Excellent "Perfect" [](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Resort-Villas.h23110.Hotel-Information) ![Waldorf Astoria Orlando - An Official Walt Disney World® Hotel](https://images.trvl-media.com/lodging/3000000/2440000/2432800/2432727/0589fd64_y.jpg) ### Waldorf Astoria Orlando - An Official Walt Disney World® Hotel 10/10 Excellent "Great stay " [](https://expedia.ca/Orlando-Hotels-Waldorf-Astoria-Orlando.h2432727.Hotel-Information) ![Lake Buena Vista Resort Village & Spa](https://images.trvl-media.com/lodging/2000000/1360000/1350900/1350864/16b6b8e7_y.jpg) ### Lake Buena Vista Resort Village & Spa 10/10 Excellent "We enjoyed our stay here. We had a 3 bwdroom suite for a very reasonable price. The rooms are a bit dated but everything was very clean. The staff was helpful and kind. It was also easy to get to everything. " [](https://expedia.ca/Orlando-Hotels-Lake-Buena-Vista-Resort-Village-Spa.h1350864.Hotel-Information) ![Hyatt Regency Orlando](https://images.trvl-media.com/lodging/1000000/10000/9600/9574/1bb0a2ac_y.jpg) ### Hyatt Regency Orlando 10/10 Excellent "Staff was great. Great location for an event at the convention center. " [](https://expedia.ca/Orlando-Hotels-Hyatt-Regency-Orlando.h9574.Hotel-Information) ## Frequently asked questions ### What should a history enthusiast expect from a trip to Winter Park? ### How many historical hotels are there in Winter Park? ### What are the must-see historical places and other sights to visit in Winter Park? ### What is a historic hotel like in Winter Park? ### What is the difference between a historic hotel and a heritage hotel? ### Do historic hotels in Winter Park have modern facilities? ## Explore a world of travel with Expedia - Lodging - More ways to book - [Spa Hotels in Aloma ](https://www.expedia.ca/Aloma-Orlando-Hotels-Spa-Hotel.0-n553248635975863638-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Hotels with Balconies in Baldwin Park ](https://www.expedia.ca/Baldwin-Park-Orlando-Hotels-Hotels-With-Balconies.0-n553248635976007760-0-tHotelswithBalconies.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Central Florida ](https://www.expedia.ca/Central-Florida-Hotels-Adults-Only-Resorts.0-0-d6048177-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - 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