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 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 two weeks [Apr 24 - Apr 26](https://www.expedia.com/Hotel-Search?regionId=7902&startDate=2026-04-24&endDate=2026-04-26&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [May 8 - May 10](https://www.expedia.com/Hotel-Search?regionId=7902&startDate=2026-05-08&endDate=2026-05-10&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=7902&startDate=2026-06-05&endDate=2026-06-07&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) ![Highchair](https://images.trvl-media.com/lodging/91000000/90220000/90211700/90211686/218ee3ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Design Room | Living area | 40-inch Smart TV with digital channels, TV](https://images.trvl-media.com/lodging/91000000/90220000/90211700/90211686/12771d68.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 9 - Apr 10 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) ![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) ![Yoga](https://images.trvl-media.com/lodging/114000000/113040000/113039700/113039630/cd1ebf76.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 $894 nightly $1,006 total Apr 19 - Apr 20 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=2026-04-22&endDate=2026-04-23®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 10/10 Excellent "En el area del water park los sillones y cojines están muy sucios " [](https://expedia.com/Orlando-Hotels-CoCo-Key-Hotel-And-Water-Resort-Orlando.h228.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 "I typically stay at this hotel when visiting, friendly staff, clean environment conveniently located " [](https://expedia.com/Orlando-Hotels-Four-Points-By-Sheraton-Orlando-International-Drive.h4262.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 you’re considering staying at Westgate, there are a few things to be aware of before booking. Loud music plays throughout the property starting around 8 AM and continues until about 10 PM at a very high volume, which made it hard to relax. Unfortunately, our AC stopped working on the last night of our stay, which was really uncomfortable. The water park is not included it’s an extra charge per person and only the lazy river and splash pad were open during our visit. We also weren’t told that it closes early at 6 PM, which was disappointing. Checkout is at 10 AM, which feels earlier than most places. Additionally, the room walls are very thin, you can clearly hear noise from neighboring rooms. Overall, it wasn’t the most comfortable or convenient stay." [](https://expedia.com/Orlando-Hotels-Westgate-Lakes-Resort-Spa-Universal-Studios-Area.h804984.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 10/10 Excellent "This place was clean, and lots of space. The room was extremely comfortable. Was able to cook in the villa.. Handy for getting ubers if needed...as they could come right to your front door. Staff was polite and courteous. They went out of their way to get us in a room next door to other family members. " [](https://expedia.com/Orlando-Hotels-Sheraton-Vistana-Villages-Resort-Villas.h539487.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 "Overall, the stay was good. The only issue we had was that we ran out of shower gel and conditioner only on our 2nd day, and we have been asking the front desk for 2 consecutive days to request housekeeping for refills. Most of the staff are friendly and accommodating, but some aren't fit for customer service. " [](https://expedia.com/Orlando-Hotels-DoubleTree-By-Hilton-At-The-Entrance-To-Universal-Orlando.h5398.Hotel-Information) ![Fairfield Inn & Suites Lake Buena Vista in Marriott Village](https://images.trvl-media.com/lodging/1000000/480000/470900/470892/w4000h2663x0y0-13fc5e39_y.jpg) ### Fairfield Inn & Suites Lake Buena Vista in Marriott Village 10/10 Excellent "Ya es la quinta vez que me quedo en ese hotel y lo amo. " [](https://expedia.com/Orlando-Hotels-Fairfield-Inn-Suites-Lake-Buena-Vista-In-Marriott-Village.h470892.Hotel-Information) ![Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando](https://images.trvl-media.com/lodging/1000000/30000/23200/23110/91c45539_y.jpg) ### Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando 10/10 Excellent "Extremely pleased with this facility. From check in to check out, everything exceeded our expectations. We will stay here again in the future." [](https://expedia.com/Orlando-Hotels-Sheraton-Vistana-Resort-Villas.h23110.Hotel-Information) ![Universal's Endless Summer Resort - Dockside Inn and Suites](https://images.trvl-media.com/lodging/34000000/33780000/33770400/33770341/c8859517_y.jpg) ### Universal's Endless Summer Resort - Dockside Inn and Suites 8/10 Good "I wasn’t made aware if there was contental breakfast " [](https://expedia.com/Orlando-Hotels-Universals-Endless-Summer-Dockside-Inn-Suites.h33770341.Hotel-Information) ![Rosen Inn Lake Buena Vista](https://images.trvl-media.com/lodging/1000000/10000/1300/1264/2a9be677_y.jpg) ### Rosen Inn Lake Buena Vista 2/10 Terrible "It was alot of false advertisement. There was no airport shuttle offered at all as advertised. Breakfast buffet was not included as stated. One person told us it was $8.00 but then said that was a mistake and it was $18.00\. Transportation to and from parks was a complete joke!!!! We were stranded because drivers kept telling us one time and then was a no show. Never will I stay here again. I will just spend the extra momey and stay on a Disney Resort and save the headache and uber/taxi fees." [](https://expedia.com/Orlando-Hotels-Rosen-Inn-Lake-Buena-Vista.h1264.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 | $1,006 | ## 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)