Title: Windermere B&B: Find the Best Bed and Breakfast from CA $94 | Expedia.ca [Hotels in Windermere](https://expedia.ca/Windermere-Hotels.d6085091.Travel-Guide-Hotels)[Vacation Rentals in Windermere](https://expedia.ca/Windermere-Vacation-Rentals.d6085091.Travel-Guide-VacationRentals)[Flights to Windermere](https://expedia.ca/Cheap-Flights-To-Windermere.d6085091.Travel-Guide-Flights)[Things to do in Windermere](https://expedia.ca/Things-To-Do-In-Windermere.d6085091.Travel-Guide-Activities)[Windermere Car Rentals](https://expedia.ca/Car-Rentals-In-Windermere.d6085091.Car-Rental-Guide)[Windermere Vacation Packages](https://expedia.ca/Windermere.d6085091.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/533000/533443-tibet-butler-preserve.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find a Bed and Breakfast in Windermere 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 prices for these dates Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6085091&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6085091&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=6085091&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=6085091&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Windermere B&B ![Design Room | Living area](https://images.trvl-media.com/lodging/91000000/90220000/90211700/90211686/7382f59b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/91000000/90220000/90211700/90211686/0452dd3d.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) ![Interior detail](https://images.trvl-media.com/lodging/91000000/90220000/90211700/90211686/e4da4ca5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Tiny Cottage in The Springs Altamonte Springs 9.8/10 Exceptional (26) "I really like this place, this is the second time I have booked here. I do consider it whenever I travel to the area." CA $224 CA $951 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Orlando-Hotels-The-Tiny-Cottage-In-The-Springs.h90211686.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/20000000/19540000/19536400/19536372/e1d103de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/20000000/19540000/19536400/19536372/f1b84b31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/20000000/19540000/19536400/19536372/ed578d36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Double Room, 1 Queen Bed](https://images.trvl-media.com/lodging/20000000/19540000/19536400/19536372/43fcfff4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kapp and Kappy B&B Historic Downtown Kissimmee 9.8/10 Exceptional (123) "It was perfect for us. The hosts were very friendly and accommodating. They just opened a brewery downtown that we were able to walk to, and we had a great time there as well. Overall a great B&B." CA $211 CA $239 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Orlando-Hotels-Kapp-And-Kappy-BB.h19536372.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/110000000/109950000/109943300/109943268/6016af14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shared kitchen facilities](https://images.trvl-media.com/lodging/110000000/109950000/109943300/109943268/aebc4dee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shared kitchen facilities](https://images.trvl-media.com/lodging/110000000/109950000/109943300/109943268/c550e596.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Single Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/110000000/109950000/109943300/109943268/b8ed6251.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Styled Bedrooms in a Villa Kissimmee 5.6/10 (5) "bad parking quiet hour not observed" CA $74 CA $180 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Orlando-Hotels-Hotel-Styled-Bedrooms-In-A-Villa.h109943268.Hotel-Information) ![Shared kitchen](https://images.trvl-media.com/lodging/121000000/120090000/120080400/120080386/47d1bfd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bathroom](https://images.trvl-media.com/lodging/121000000/120090000/120080400/120080386/378ef345.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Room, 2 Double Beds, Non Smoking](https://images.trvl-media.com/lodging/121000000/120090000/120080400/120080386/0f6bd9e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/121000000/120090000/120080400/120080386/4952149d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Gathering Place Kissimmee 2.0/10 (1) "Not to clean or to friendly " CA $82 CA $94 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Orlando-Hotels-The-Gathering-Place.h120080386.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=6085091&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.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWindermere-Bed-And-Breakfast.d6085091-aaBedAndBreakfast.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindermere-Bed-And-Breakfast.d6085091-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Windermere Hotel Reviews ![Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center](//images.trvl-media.com/lodging/62000000/61350000/61340900/61340843/2b752fc1_y.jpg) ### Fairfield by Marriott Inn & Suites Orlando at FLAMINGO CROSSINGS(r) Town Center 10/10 Excellent "This is an ideal location to Disney Parks (15 minutes or less to all of them) and has enough dining options for when you’re done with the parks. We appreciated the covered parking and walkability to the Flamingo Crossing plaza. Target is in the plaza for anyone who may have forgotten anything. The hotel was clean and free breakfast was an added bonus. The staff was very hospitable. " [](https://expedia.ca/Orlando-Hotels-Fairfield-Inn-Suites-By-Marriott-Orlando-Flamingo-CrossingWestern-Entrance.h61340843.Hotel-Information) ![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) ![Home2 Suites by Hilton Orlando at Flamingo Crossings](//images.trvl-media.com/lodging/59000000/58080000/58072600/58072517/9a8a6f4d_y.jpg) ### Home2 Suites by Hilton Orlando at Flamingo Crossings 10/10 Excellent "Everything was perfect " [](https://expedia.ca/Orlando-Hotels-Home2-Suites-By-Hilton-Orlando-Flamingo-Crossings.h58072517.Hotel-Information) ![DoubleTree by Hilton Orlando Airport](//images.trvl-media.com/lodging/1000000/20000/12300/12270/5d85f82f_y.jpg) ### DoubleTree by Hilton Orlando Airport 10/10 Excellent "Very friendly staff and clean facilities. " [](https://expedia.ca/Orlando-Hotels-DoubleTree-By-Hilton-Orlando-Airport.h12270.Hotel-Information) ![Universal's Cabana Bay Beach Resort](//images.trvl-media.com/lodging/6000000/5970000/5963300/5963292/63940f45_y.jpg) ### Universal's Cabana Bay Beach Resort 10/10 Excellent "It was nice I saw kids enjoying the lazy river on one pool and the slide had kids playing with no problem. I have 7 kids and I think they would really enjoy this resort." [](https://expedia.ca/Orlando-Hotels-Universals-Cabana-Bay-Beach-Resort.h5963292.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) ![The Grove Resort & Water Park Orlando](//images.trvl-media.com/lodging/5000000/4700000/4691700/4691657/c5a7d392_y.jpg) ### The Grove Resort & Water Park Orlando 10/10 Excellent "Our stay was great!" [](https://expedia.ca/Orlando-Hotels-The-Grove-Resort-Water-Park-Orlando.h4691657.Hotel-Information) ![Sheraton Vistana Villages Resort Villas, I-Drive/Orlando](//images.trvl-media.com/lodging/1000000/540000/539500/539487/88f9edce_y.jpg) ### Sheraton Vistana Villages Resort Villas, I-Drive/Orlando 10/10 Excellent "Absoluteky enjoyed my week there, can not wait to come back. Perfect for families and solo travelers :) " [](https://expedia.ca/Orlando-Hotels-Sheraton-Vistana-Villages-Resort-Villas.h539487.Hotel-Information) ![Marriott's Grande Vista](//images.trvl-media.com/lodging/1000000/860000/853600/853519/77708f65_y.jpg) ### Marriott's Grande Vista 10/10 Excellent "Very nice property for couples or families." [](https://expedia.ca/Orlando-Hotels-Marriotts-Grande-Vista.h853519.Hotel-Information) ## Find out more about Windermere ## Windermere B&B information | Number of reviews | 129 | | --- | --- | | Accommodation | 12 B&B | | Lowest Price | CA $94 | | Highest Price | CA $951 | ## Frequently asked questions ### Searching for B&Bs in Windermere? > If you're looking for something a little more offbeat than your standard hotel experience, a stay at a bed and breakfast might be the perfect option for your trip. If you're interested in playing some golf on your trip, Isleworth Golf and Country Club is a good spot to tee off. ### Are you thinking about a B&B for your stay? > With attentive service, opportunities to interact with the owner, and top-rated breakfasts, B&Bs offer a truly one-of-a-kind environment. ### What are the best B&Bs in Windermere? > Below are some B&Bs in the area: [Kapp and Kappy B&B](https://www.expedia.ca/Orlando-Hotels-Kapp-And-Kappy-BB.h19536372.Hotel-Information): 3 rooms. 15.9 mi (25.5 km) from the heart of Windermere. Enjoy the free full breakfast and unique décor. [Styled Bedrooms in a Resort](https://www.expedia.ca/Orlando-Hotels-Styled-Bedrooms-In-A-Resort.h119256613.Hotel-Information): 6 rooms. 18.4 mi (29.7 km) from the downtown core. [Hotel Styled Bedrooms in a Villa](https://www.expedia.ca/Orlando-Hotels-Hotel-Styled-Bedrooms-In-A-Villa.h109943268.Hotel-Information): 4 rooms. Situated 14.7 mi (23.6 km) from the heart of Windermere. [Oakland Manor House](https://www.expedia.ca/Winter-Garden-Hotels-Oakland-Manor-House.h113039630.Hotel-Information): 5 rooms. 7.2 mi (11.6 km) from the heart of downtown.[The Tiny Cottage in The Springs](https://www.expedia.ca/Orlando-Hotels-The-Tiny-Cottage-In-The-Springs.h90211686.Hotel-Information): 2 rooms. Located 16.5 mi (26.6 km) from the core of Windermere. Enjoy the unique décor and fireplace in the lobby. ### What's the best time of year to stay at a B&B in Windermere? > When you're dreaming of a getaway to Windermere, be sure to take into account the year-round temperatures. The hottest months are usually August and July with an average temp of 81°F, while the coldest months are January and February with an average of 64°F. The rainiest months in Windermere are August, July, September, and June, with each month seeing an average of 8 inches of rainfall. ### What is there to do in Windermere? > Spend some time exploring Lake Butler and Tibet Butler Preserve if you're hoping to see some of the area's natural features. You might check out Isleworth Golf and Country Club if you have time to see more of the area. ### How can I get to and around Windermere? > You can plan your excursions in and around Windermere ahead of time with these transportation options. Fly into Orlando Intl. Airport (MCO), which is located 14.5 mi (23.3 km) away from the city center. Otherwise, look for flights into Kissimmee, FL (ISM-Kissimmee Gateway), which is 15.2 mi (24.4 km) away. 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