Title: 20 Best B&B in Winter Park, FL - Bed and Breakfast from $699 | Expedia.com [Winter Park Travel Guide](https://expedia.com/Winter-Park.dx7902)[Hotels in Winter Park](https://expedia.com/Winter-Park-Hotels.d7902.Travel-Guide-Hotels)[Vacation Rentals in Winter Park](https://expedia.com/Winter-Park-Vacation-Rentals.d7902.Travel-Guide-VacationRentals)[Flights to Winter Park](https://expedia.com/Cheap-Flights-To-Winter-Park.d7902.Travel-Guide-Flights)[Things to do in Winter Park](https://expedia.com/Things-To-Do-In-Winter-Park.d7902.Travel-Guide-Activities)[Car Rentals in Winter Park](https://expedia.com/Car-Rentals-In-Winter-Park.d7902.Car-Rental-Guide)[Winter Park Vacation Packages](https://expedia.com/Winter-Park.d7902.Destination-Travel-Guides) ![](https://images.trvl-media.com/place/553248621532654339/aef9d03a-cd86-4dcc-8e9d-049aef598da5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/553248621532654339/aef9d03a-cd86-4dcc-8e9d-049aef598da5.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates Next weekend [Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=7902&startDate=2026-04-10&endDate=2026-04-12&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Apr 17 - Apr 19](https://www.expedia.com/Hotel-Search?regionId=7902&startDate=2026-04-17&endDate=2026-04-19&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=7902&startDate=2026-05-01&endDate=2026-05-03&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=7902&startDate=2026-05-29&endDate=2026-05-31&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winter Park bed & breakfast ![Design Room | Living area | 40-inch Smart TV with digital channels, TV](https://images.trvl-media.com/lodging/91000000/90220000/90211700/90211686/747b8634.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/91000000/90220000/90211700/90211686/8addfbd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/91000000/90220000/90211700/90211686/e4da4ca5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Highchair](https://images.trvl-media.com/lodging/91000000/90220000/90211700/90211686/218ee3ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Tiny Cottage in The Springs [](https://www.expedia.com/Orlando-Hotels-The-Tiny-Cottage-In-The-Springs.h90211686.Hotel-Information) Altamonte Springs 9.8/10 Exceptional (26 reviews) "I really like this place, this is the second time I have booked here. I do consider it whenever I travel to the area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anastasia $678 nightly $699 total Apr 6 - Apr 7 Total with taxes and fees [](https://www.expedia.com/Orlando-Hotels-The-Tiny-Cottage-In-The-Springs.h90211686.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/114000000/113040000/113039700/113039630/03f5acec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/114000000/113040000/113039700/113039630/635d6269.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Staircase](https://images.trvl-media.com/lodging/114000000/113040000/113039700/113039630/93dfb53c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113040000/113039700/113039630/a9e3153a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oakland Manor House [](https://www.expedia.com/Winter-Garden-Hotels-Oakland-Manor-House.h113039630.Hotel-Information) Oakland $891 nightly $1,003 total May 6 - May 7 Total with taxes and fees [](https://www.expedia.com/Winter-Garden-Hotels-Oakland-Manor-House.h113039630.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.com/Hotel-Search?startDate=2026-04-19&endDate=2026-04-20®ionId=7902&adults=2&lodging=BED_AND_BREAKFAST&sort=RECOMMENDED&openPlayBack=true) ![](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.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinter-Park-Bed-And-Breakfast.d7902-aaBedAndBreakfast.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinter-Park-Bed-And-Breakfast.d7902-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Winter Park Hotel Reviews ![Coco Key Hotel & Water Park Resort](https://images.trvl-media.com/lodging/1000000/10000/300/228/84c2249c_y.jpg) ### Coco Key Hotel & Water Park Resort 8/10 Good "N/a" [](https://expedia.com/Orlando-Hotels-CoCo-Key-Hotel-And-Water-Resort-Orlando.h228.Hotel-Information) ![DoubleTree by Hilton at the Entrance to Universal Orlando](https://images.trvl-media.com/lodging/1000000/10000/5400/5398/cae40483_y.jpg) ### DoubleTree by Hilton at the Entrance to Universal Orlando 8/10 Good "The poolside seating was nicely spread out and comfortable. The lobby restaurant service was kind and professional. The food was excellent. My compliments to the front desk and restaurant staff. Our family stayed in on two rooms and both of the rooms were adaquate. The rooms (#327 & #323) both shared a musty and damp odor. Best described as unpleasant. While this may have been the result of the most recent guests, it definitely should have been addressed prior to the rooms being rented to new guests. This condition was brought to the attention of the front desk staff upon our check out the morning of 3/23\. I can only hope that this condition has been addressed and a process has been put in place to avoid a repeat of this unfortunate situation. Sincerely, William and Jacqueline Sullivan " [](https://expedia.com/Orlando-Hotels-DoubleTree-By-Hilton-At-The-Entrance-To-Universal-Orlando.h5398.Hotel-Information) ![B&B Hotel Orlando International Drive Near Universal - Newly Renovated!](https://images.trvl-media.com/lodging/1000000/30000/26800/26703/ca31fce1_y.jpg) ### B&B Hotel Orlando International Drive Near Universal - Newly Renovated! 4/10 Poor "No TV, no WiFi. Laundry service didn’t work. " [](https://expedia.com/Orlando-Hotels-Floridian-Express-Extended-Stay-Hotel.h26703.Hotel-Information) ![Westgate Lakes Resort & Spa Universal Studios Area](https://images.trvl-media.com/lodging/1000000/810000/805000/804984/ffaf091a_y.jpg) ### Westgate Lakes Resort & Spa Universal Studios Area 2/10 Terrible "If I can rate this hotel, a zero I would have rated a zero, but you guys would not allow me to do it. I would never stay at Westgate resort and spa ever again in my life. I shouldn’t have to pay to use a waterpark that is being advertised as if it’s included in the nightly rates. This resort gets a zero from me and I wish I can get my money back from staying there, a matter of fact, I didn’t even stay the fourth night. That’s just how horrible the resort was." [](https://expedia.com/Orlando-Hotels-Westgate-Lakes-Resort-Spa-Universal-Studios-Area.h804984.Hotel-Information) ![Four Points by Sheraton Orlando International Drive](https://images.trvl-media.com/lodging/1000000/10000/4300/4262/c6e39ea9_edited_40eb_y.jpg) ### Four Points by Sheraton Orlando International Drive 10/10 Excellent "The best was the breakfast buffet and speaking with Alex, our entire party of 5 thought he was the greatest. HE equally paid all patrons with great attention.Thank you Alex, you made our stay enjoyable by starting our day off wonderful." [](https://expedia.com/Orlando-Hotels-Four-Points-By-Sheraton-Orlando-International-Drive.h4262.Hotel-Information) ![Orlando International Drive North Hotel](https://images.trvl-media.com/lodging/1000000/50000/41500/41493/fcd15e0d_y.jpg) ### Orlando International Drive North Hotel 10/10 Excellent "Everything was great" [](https://expedia.com/Orlando-Hotels-Orlando-International-Drive-North-Hotel.h41493.Hotel-Information) ![Rosen Inn at Pointe Orlando](https://images.trvl-media.com/lodging/1000000/10000/8900/8892/8068a653_y.jpg) ### Rosen Inn at Pointe Orlando 10/10 Excellent "Great location. Staff is very friendly. Close to many attractions. " [](https://expedia.com/Orlando-Hotels-Rosen-Inn-At-Pointe-Orlando.h8892.Hotel-Information) ![Universal's Endless Summer Resort - Surfside Inn and Suites](https://images.trvl-media.com/lodging/28000000/27530000/27522600/27522522/0bad3378_y.jpg) ### Universal's Endless Summer Resort - Surfside Inn and Suites 6/10 Okay "Check in took ENTIRELY too long, and that was without a line. It took nearly 30 minutes. That needs to improve. The room was smaller than I expected. The floors were laminate, which was not comfortable to walk on. The room was quite noisy, and if you were in the bathroom, you could hear your neighbors conversation as if it were in your own room, nevermind stomping of anyone in the hallway and above you. The shower was fine, but the products were just so-so. To turn the shower on, we had to use both hands as the handle was quite difficult to maneuver. At night, you could hear noise (tower 2, garage/parking lot views) from the street and from the hallway. I did love the shuttle service, and the food was fairly priced inside the hotel. The pool was just so-so. It was cold, and the lifeguards blew their whistle so frequently it was hard to relax there. Overall, I'm not sure I would stay here again, but I hope this review is helpful for someone!" [](https://expedia.com/Orlando-Hotels-Universals-Endless-Summer-Resort-Surfside-Inn-And-Suites.h27522522.Hotel-Information) ![Sheraton Vistana Villages Resort Villas, I-Drive/Orlando](https://images.trvl-media.com/lodging/1000000/540000/539500/539487/4ca8f177_y.jpg) ### Sheraton Vistana Villages Resort Villas, I-Drive/Orlando 4/10 Poor "They push the time share and have expensive food and drinks. This place has changed the last few years and not for the better. " [](https://expedia.com/Orlando-Hotels-Sheraton-Vistana-Villages-Resort-Villas.h539487.Hotel-Information) ## Find out more about Winter Park ## Winter Park B&B information | Number of reviews | 26 | | ----------------- | ------ | | Accommodation | 18 B&B | | Lowest Price | $699 | | Highest Price | $1,003 | ## Frequently asked questions ### What is the nightly rate for a Bed and Breakfast in Winter Park? ### When is the best time to book a Bed & Breakfast in Winter Park? > February, in particular, stands out as the most popular month, offering a festive atmosphere with numerous events and plenty of fresh powder. During this time, you can enjoy not only skiing but also snowshoeing and snowmobiling, all while surrounded by the stunning Rocky Mountain scenery. The lively après-ski scene adds to the experience, making it an excellent choice for those looking to unwind after an active day. > > > For travelers seeking a more budget-friendly option, consider visiting in early May. During this shoulder season, you can enjoy the beauty of the mountains as the snow begins to melt and flowers start to bloom. It's a quieter time, great for exploring local trails and soaking in the serene landscapes without the crowds. ### What is the difference between a Winter Park Bed and Breakfast and a hotel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - [Orlando Hotels ](https://www.expedia.com/Orlando-Hotels.d178294.Travel-Guide-Hotels) - [Resorts in Orlando ](https://www.expedia.com/Orlando-Resorts.d178294-aaResorts.Travel-Guide-Accommodation) - [Cheap Hotels in Orlando ](https://www.expedia.com/Orlando-Hotels-Cheap-Hotels.0-0-d178294-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with Free Airport Shuttle in Orlando ](https://www.expedia.com/Orlando-Hotels-Hotels-With-Free-Airport-Shuttle.0-0-d178294-tHotelswithFreeAirportShuttle.Travel-Guide-Filter-Hotels) - [Hotels near Albin Polasek Museum and Sculpture Gardens ](https://www.expedia.com/Albin-Polasek-Museum-And-Sculpture-Gardens-Hotels.0-l6154778-0.Travel-Guide-Filter-Hotels) - [Hotels near Universal Studios Florida ](https://www.expedia.com/Universal-Studios-Florida-Hotels.0-l6049239-0.Travel-Guide-Filter-Hotels) - [All-Inclusive Resorts in Orlando ](https://www.expedia.com/Orlando-Hotels-All-Inclusive-Hotel.0-0-d178294-tAllinclusiveHotel.Travel-Guide-Filter-Hotels) - [Hotels near Winter Park Country Club ](https://www.expedia.com/Winter-Park-Country-Club-Hotels.0-l6239878-0.Travel-Guide-Filter-Hotels) - [Hotels near Copland Tennis Stadium ](https://www.expedia.com/Copland-Tennis-Stadium-Hotels.0-l553248621563220224-0.Travel-Guide-Filter-Hotels) - [Hotels near Rollins College ](https://www.expedia.com/Rollins-College-Hotels.0-l6154361-0.Travel-Guide-Filter-Hotels) - [Hotels near Morse Museum of American Art ](https://www.expedia.com/Morse-Museum-Of-American-Art-Hotels.0-l6154772-0.Travel-Guide-Filter-Hotels) - [Hotels near Winter Park Corner Shopping Center ](https://www.expedia.com/Winter-Park-Corner-Shopping-Center-Hotels.0-l553248621532654341-0.Travel-Guide-Filter-Hotels) - [Hotels near Casa Feliz Historic Home Museum ](https://www.expedia.com/Casa-Feliz-Historic-Home-Museum-Hotels.0-l6154784-0.Travel-Guide-Filter-Hotels) - [Hotels near Winter Park Station ](https://www.expedia.com/Winter-Park-Station-Hotels.d6176530.Travel-Guide-Hotels) - [Hotels near Barker Stadium ](https://www.expedia.com/Barker-Stadium-Hotels.0-l553248621563220225-0.Travel-Guide-Filter-Hotels) - [Hotels near Kraft Azalea Gardens ](https://www.expedia.com/Kraft-Azalea-Gardens-Hotels.0-l553248621532654339-0.Travel-Guide-Filter-Hotels) - [Hotels near Virginia S. 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Nelson Rose Garden ](https://www.expedia.com/Virginia-S-Nelson-Rose-Garden-Orlando.d6239868.Vacation-Attraction) - [Winter Park History Museum ](https://www.expedia.com/Winter-Park-History-Museum-Orlando.d553248621532654329.Vacation-Attraction) - [Cahall Sandspur Field ](https://www.expedia.com/Cahall-Sandspur-Field-Orlando.d6239859.Vacation-Attraction) - [Alfond Swimming Pool ](https://www.expedia.com/Alfond-Swimming-Pool-Orlando.d553248621558036313.Vacation-Attraction) - [All Fired Up ](https://www.expedia.com/All-Fired-Up-Orlando.d553248621532654330.Vacation-Attraction) - [Lake Virginia ](https://www.expedia.com/Lake-Virginia-Orlando.d553248621532654331.Vacation-Attraction) - [Crealde School of Art ](https://www.expedia.com/Crealde-School-Of-Art-Orlando.d6239848.Vacation-Attraction) - [Hannibal Square Heritage Center ](https://www.expedia.com/Hannibal-Square-Heritage-Center-Orlando.d553248621532654328.Vacation-Attraction) - [Winter Park Playhouse ](https://www.expedia.com/Winter-Park-Playhouse-Orlando.d553248621561885914.Vacation-Attraction) - [Winter Park Tennis Center ](https://www.expedia.com/Winter-Park-Tennis-Center-Orlando.d636723274468732928.Vacation-Attraction) - [Lake Rose ](https://www.expedia.com/Lake-Rose-Orlando.d6360988.Vacation-Attraction) - [Winter Park Village ](https://www.expedia.com/Winter-Park-Village-Orlando.d6239900.Vacation-Attraction) - [Howell Branch Preserve Pavilion ](https://www.expedia.com/Howell-Branch-Preserve-Pavilion-Orlando.d553248621532654340.Vacation-Attraction) - [Mead Garden ](https://www.expedia.com/Mead-Garden-Orlando.d6239861.Vacation-Attraction) - [Hollie Anna Shopping Center ](https://www.expedia.com/Hollie-Anna-Shopping-Center-Orlando.d553248621563220220.Vacation-Attraction) - [Lake Maitland Terrace Marina ](https://www.expedia.com/Lake-Maitland-Terrace-Marina-Orlando.d553248621563220228.Vacation-Attraction) - [Enzian Theater ](https://www.expedia.com/Enzian-Theater-Orlando.d6154880.Vacation-Attraction) - [Winter Pines Golf Club ](https://www.expedia.com/Winter-Pines-Golf-Club-Orlando.d6239892.Vacation-Attraction) - [Lee Road Shopping Center ](https://www.expedia.com/Lee-Road-Shopping-Center-Fairview-Shores.d553248621563220222.Vacation-Attraction) - [Visit Orwin Manor ](https://www.expedia.com/Orlando-Orwin-Manor.dx553248635976471367) - [Lake Lily Park ](https://www.expedia.com/Lake-Lily-Park-Orlando.d553248621532654336.Vacation-Attraction) - [Car rental Orlando Airport (MCO) ](https://www.expedia.com/Car-Rentals-In-Orlando-Intl.d5194573.Car-Rental-Guide) - [Car rentals near Orlando ](https://www.expedia.com/Car-Rentals-In-Orlando.d178294.Car-Rental-Guide) - [Car rentals near Albin Polasek Museum and Sculpture Gardens ](https://www.expedia.com/Car-Rentals-In-Albin-Polasek-Museum-And-Sculpture-Gardens.d6154778.Car-Rental-Guide) - [Car rentals near Winter Park Corner Shopping Center ](https://www.expedia.com/Car-Rentals-In-Winter-Park-Corner-Shopping-Center.d553248621532654341.Car-Rental-Guide) - [Car rentals near Rollins College ](https://www.expedia.com/Car-Rentals-In-Rollins-College.d6154361.Car-Rental-Guide) - [Compact Car Rentals near Rollins College ](https://www.expedia.com/Compact-Car-Rentals-In-Rollins-College.d6154361-tCompact.Car-Rental-Guide-Class) - [Car rentals near Aloma ](https://www.expedia.com/Car-Rentals-In-Aloma.d553248635975863638.Car-Rental-Guide) - [Things to do in Orlando ](https://www.expedia.com/Things-To-Do-In-Orlando.d178294.Travel-Guide-Activities)