Title: Book the Best HISTORIC Hotels in Winter Garden in 2025 | Expedia.ca [Winter Garden Travel Guide](https://expedia.ca/Winter-Garden.dx7898)[Hotels in Winter Garden](https://expedia.ca/Winter-Garden-Hotels.d7898.Travel-Guide-Hotels)[Vacation Rentals in Winter Garden](https://expedia.ca/Winter-Garden-Vacation-Rentals.d7898.Travel-Guide-VacationRentals)[Flights to Winter Garden](https://expedia.ca/Cheap-Flights-To-Winter-Garden.d7898.Travel-Guide-Flights)[Things to do in Winter Garden](https://expedia.ca/Things-To-Do-In-Winter-Garden.d7898.Travel-Guide-Activities)[Winter Garden Car Rentals](https://expedia.ca/Car-Rentals-In-Winter-Garden.d7898.Car-Rental-Guide)[Winter Garden Vacation Packages](https://expedia.ca/Winter-Garden.d7898.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/1/37b5977531ce6620ae360dd863ce8f7c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Historic Hotels in Winter Garden, FL from CA $94 ![](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 Garden Historic Hotels Tonight [Oct 12 - Oct 13](https://www.expedia.ca/Hotel-Search?regionId=7898&startDate=2025-10-12&endDate=2025-10-13&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=7898&startDate=2025-10-13&endDate=2025-10-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=7898&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=7898&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winter Garden Historic Hotels ![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119030000/119022200/119022119/9423d671.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/120000000/119030000/119022200/119022119/c20e1c6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/120000000/119030000/119022200/119022119/20761080.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119030000/119022200/119022119/3c8cc479.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chic Studio Apartment in Near Downtown Winter Garden Winter Garden CA $61 CA $255 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Winter-Garden-Hotels-Chic-Studio-Apartment-In-Near-Downtown-Winter-Garden.h119022119.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/49000000/48650000/48644000/48643933/181f625e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/49000000/48650000/48644000/48643933/f2c6e82c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/49000000/48650000/48644000/48643933/c92a25e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/49000000/48650000/48644000/48643933/d95d3737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Oak View Place.. Oakland 9.2/10 Wonderful (10) "The VRBO looked brand new and I only knew it was not because of the reviews from previous years. The live oak trees on the property added to the beauty of the surroundings." CA $252 CA $407 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Winter-Garden-Hotels-The-Oak-View-Place.h48643933.Hotel-Information) ![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119030000/119028000/119027974/d4a8b5ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/120000000/119030000/119028000/119027974/88b53697.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119030000/119028000/119027974/c7da1061.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/120000000/119030000/119028000/119027974/10d759a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfy Studio Apartment Near Downtown and Disney Winter Garden CA $58 CA $251 total includes taxes & fees Oct 17 - Oct 18 [](https://www.expedia.ca/Winter-Garden-Hotels-Comfy-Studio-Apartment-Near-Downtown-And-Disney.h119027974.Hotel-Information) ![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119030000/119020700/119020658/f0db621a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/120000000/119030000/119020700/119020658/44914ad3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/120000000/119030000/119020700/119020658/da81ba0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/120000000/119030000/119020700/119020658/9aaf8917.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cute Studio on the Bike Trail Winter Garden CA $59 CA $252 total includes taxes & fees Oct 18 - Oct 19 [](https://www.expedia.ca/Winter-Garden-Hotels-Cute-Studio-On-The-Bike-Trail.h119020658.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/120000000/119030000/119021700/119021668/01c5f0a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119030000/119021700/119021668/c1506232.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119030000/119021700/119021668/a79463a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/120000000/119030000/119021700/119021668/15d5dd24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Large Studio Apartment Near Downtown Winter Garden CA $61 CA $254 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Winter-Garden-Hotels-Large-Studio-Apartment-Near-Downtown.h119021668.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/120000000/119030000/119027800/119027767/65641bb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119030000/119027800/119027767/dd47f3b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/120000000/119030000/119027800/119027767/9d323104.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119030000/119027800/119027767/799ae9db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Studio Apartment Near Downtown and Disney Winter Garden 10/10 Exceptional (1) "Had a great stay. The location near downtown was perfect. Would stay again." CA $63 CA $256 total includes taxes & fees Oct 20 - Oct 21 [](https://www.expedia.ca/Winter-Garden-Hotels-Charming-Studio-Apartment-Near-Downtown-And-Disney.h119027767.Hotel-Information) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/910000/904800/904781/081c4ef9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/910000/904800/904781/b44c6a0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/910000/904800/904781/e86e039a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, Two Queen Beds, Accessible | Minibar](https://images.trvl-media.com/lodging/1000000/910000/904800/904781/0287c161.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Orlando Intl Dr N International Drive District 9.2/10 Wonderful (1029) "Nice hotel and near everything " CA $119 CA $134 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Orlando-Hotels-Hampton-Inn-Suites-Orlando-International-Drive-North.h904781.Hotel-Information)   ![Water park](https://images.trvl-media.com/lodging/1000000/10000/300/228/73a42af2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)   ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/10000/300/228/3eb04fcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)   ![Property amenity](https://images.trvl-media.com/lodging/1000000/10000/300/228/4e350fa6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)   ![Arcade](https://images.trvl-media.com/lodging/1000000/10000/300/228/dd28c9c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)    ### CoCo Key Hotel and Water Resort  International Drive District 8.0/10 Very good (3615) "Very friendly staff and budget friendly hotel with great water park and restaurants close by." CA $107 CA $191 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Orlando-Hotels-CoCo-Key-Hotel-And-Water-Resort-Orlando.h228.Hotel-Information)  ![Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/10000/800/702/74ea6ef2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Accessible, Kitchenette | Private kitchenette](https://images.trvl-media.com/lodging/1000000/10000/800/702/38c9c0f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, open 9 AM to 10:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/800/702/e1a4eff1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![42-inch LED TV with cable channels, TV](https://images.trvl-media.com/lodging/1000000/10000/800/702/43789e2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Home 1 Suites Extended Stay - Kissimmee Kissimmee 6.6/10 (1002) "Ive stayed at this hotel years ago " CA $83 CA $94 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Orlando-Hotels-Home-1-Suites-Extended-Stay-Kissimmee.h702.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/1000000/10000/4000/3916/1fbd324f.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) ![Courtyard view](https://images.trvl-media.com/lodging/1000000/10000/4000/3916/ab16f193.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wyndham I-Drive Avanti Resort & Conference Center International Drive District 7.4/10 Good (3689) "Very clean, friendly staff." CA $65 CA $101 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Orlando-Hotels-Avanti-Palms-Resort-And-Conference-Center.h3916.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=2025-10-26&endDate=2025-10-27®ionId=7898&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Winter Garden Hotel Reviews ![Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando](//images.trvl-media.com/lodging/1000000/30000/23200/23110/ade3b60d_y.jpg) ### Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando 10/10 Excellent "Plenty of swimming areas for kids and volleyball area. I especially loved the calming lake view from our balcony." [](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Resort-Villas.h23110.Hotel-Information) ![Rosen Inn Lake Buena Vista](//images.trvl-media.com/lodging/1000000/10000/1300/1264/2a9be677_y.jpg) ### Rosen Inn Lake Buena Vista 10/10 Excellent "Staff is always friendly and rooms are always clean! My go to hotel for an off property Disney trip! " [](https://expedia.ca/Orlando-Hotels-Rosen-Inn-Lake-Buena-Vista.h1264.Hotel-Information) ![Hilton Vacation Club Aqua Sol Orlando West](//images.trvl-media.com/lodging/1000000/700000/692700/692650/0986573c_y.jpg) ### Hilton Vacation Club Aqua Sol Orlando West 10/10 Excellent "Great start for a family vacation. The rooms don’t get dark due to hallway lights and curtain rods that are set away from the window too far. Other than that it was perfect for what we needed. " [](https://expedia.ca/Orlando-Hotels-Liki-Tiki-Village.h692650.Hotel-Information) ![Holiday Inn Resort Kissimmee by the Parks by IHG](//images.trvl-media.com/lodging/1000000/60000/52900/52821/48f5f27b_y.jpg) ### Holiday Inn Resort Kissimmee by the Parks by IHG 10/10 Excellent "The room was clean. The furniture was outdated but it was clean. " [](https://expedia.ca/Orlando-Hotels-Holiday-Inn-Resort-Kissimmee-By-The-Parks-By-IHG.h52821.Hotel-Information) ![Hyatt Regency Orlando](//images.trvl-media.com/lodging/1000000/10000/9600/9574/1bb0a2ac_y.jpg) ### Hyatt Regency Orlando 10/10 Excellent "Everything Amazing " [](https://expedia.ca/Orlando-Hotels-Hyatt-Regency-Orlando.h9574.Hotel-Information) ## Frequently asked questions ### What should a history buff expect from a stay in Winter Garden? > The historical sites in Winter Garden are probably a big part of your travel plans. While you're here, you might want to visit the fun-filled theme parks and array of shops. And also relish a stop at the top-notch restaurants in this relaxing area. ### How many historical hotels are there in Winter Garden? > In Winter Garden, there are 350 hotels and other lodging options bookable on Expedia but not many designated as historic hotels. ### What are the most important historical places and other sights to visit in Winter Garden? > Landmarks like Central Florida Railroad Museum and Garden Theatre in Winter Garden might be worth a visit. Cultural venues include Winter Garden Art Association and Winter Garden Heritage Museum. In the area, you'll also find Universal Studios Florida and Universal Orlando Resort. ### What is a historic hotel like in Winter Garden? > By choosing a historic hotel, you can enjoy a vacation in a place that has an officially recognized national historic designation. A palace, castle, grand home or even an old police station, pub, lodge, or skyscraper can be transformed into a historic hotel as long as it's of special interest. Traditional architecture and period features are typically found in the communal spaces and guestrooms of historic hotels in Winter Garden, giving a real sense of character. ### What is the difference between a historic hotel and a heritage hotel? > "Heritage hotel" is a term often used in Asia and Europe, wheareas the term "historic hotel" is more commonly used in the U.S. but overall the terms are quite similar. The architecture and building of historic hotels are generally what's most significant. For a heritage hotel, mainly, it's cultural value and how it influenced the community. ### Do historic hotels in Winter Garden have modern facilities? > Hotel interiors feature the modern conveniences and safety features you might expect, though efforts have been made to preserve the historic aspects and traditions. Private rooms with updated bathroom facilities, free WiFi, and the amenities found in any hotel will also be available in a historic hotel. 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