Plan your trip

A lakeside community with houses and boats.

Book Windermere Bed & Breakfast

Check prices for these dates

Check prices for these dates, December 15 – 16, 2026

View in a map

Our top choices for Windermere bed & breakfast

1. Tempo Room Lodgings

A rectangular swimming pool with a hot tub, surrounded by a brick patio and palm trees.

2. Hotel Styled Bedrooms in a Villa

A pool area with a clear view of the surrounding buildings, a blue inflatable shark, and several lounge chairs.

3. Kapp and Kappy B&B

A covered porch with wooden chairs and a ceiling fan.

4. The Gathering Place

A swimming pool with blue tiles, a glass-enclosed patio with blue lounge chairs, and a gray sofa with red cushions.

5. The Tiny Cottage in The Springs

A modern living room with a white sofa, a dining table with chairs, a fireplace, and a staircase leading to an upper level.

6. Styled Bedrooms in a Resort

A swimming pool with blue tiles, a glass-enclosed patio with blue lounge chairs, and a gray sofa with red cushions.

7. Serene 1-bedroom bed & breakfast in lovely Orlando neighborhood

A swimming pool with a hot tub, surrounded by a covered patio area with chairs and a grill.

8. PrivateOakForest RanchFirepit, BBQ&FamilyRetreat

A cozy room with a sofa, armchair, and a small table, large windows with a view of the parking lot, and a ceiling with hanging plants.

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

Learn more about Windermere

Nestled among pristine lakes, this charming town offers a peaceful escape with upscale golf courses and country clubs. Nature lovers can explore the Tibet-Butler Preserve's trails, while four-legged friends enjoy romping at Buena Vista Place Dog Park.

See all hotels in Windermere

A lakeside community with houses and boats.

Frequently Asked Questions

What is the nightly rate for a B&B in Windermere?

Prices for B&Bs in Windermere often vary, but you can find a great deal from $114 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Windermere B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.

When is the best time to book a Bed and Breakfast in Windermere?

The most popular time to book a B&B in Windermere is from July to September, when the area comes alive with outdoor enthusiasts seeking the stunning landscapes and recreational activities that this beautiful region offers. During these peak months, visitors can enjoy warm temperatures averaging in the mid-70s to low 80s Fahrenheit, making it ideal for hiking, boating, and exploring the charming local attractions.

July stands out as the busiest month, with an array of festivals and events drawing crowds from near and far. Adventurers can take advantage of the long, sunny days to experience everything from tranquil boat rides on the lake to invigorating hikes along scenic trails that overlook breathtaking vistas.

For those seeking a more budget-friendly option, consider planning your visit in October. This month offers a quieter experience, superb for enjoying the tranquility of the area while still taking in the beautiful fall foliage. Crisp autumn air presents an excellent opportunity for leisurely walks and cozy evenings by the fireplace.

What is the difference between a Windermere Bed and Breakfast and a hotel?

Every Windermere B&B has its own unique feel. Whether it’s a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Windermere B&Bs.

Explore a world of travel with Expedia