Book Windermere Bed & Breakfast

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Our top choices for Windermere bed & breakfast

Kapp and Kappy B&B

Kapp and Kappy B&B
3.5 star property
Historic Downtown Kissimmee
9.8 out of 10, Exceptional, (140 reviews)
"Excellent property"
United States
Maikel
$146 nightly
The price is $165
Apr 30 - May 1
Total with taxes and fees
Kapp and Kappy B&B

The Tiny Cottage in The Springs

The Tiny Cottage in The Springs
4.0 star property
Altamonte Springs
9.8 out of 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
Anastasia
$722 nightly
The price is $749
Apr 29 - Apr 30
Total with taxes and fees
The Tiny Cottage in The Springs

Hotel Styled Bedrooms in a Villa

Hotel Styled Bedrooms in a Villa
3.0 star property
Kissimmee
5.8 out of 10, (8 reviews)
"I didn’t know it was a house being shared by like 6 other tenants and parking was a pain"
United States
Veronica
$114 nightly
The price is $129
May 2 - May 3
Total with taxes and fees
Hotel Styled Bedrooms in a Villa

PrivateOakForest RanchFirepit, BBQ&FamilyRetreat

PrivateOakForest RanchFirepit, BBQ&FamilyRetreat
Clermont
10.0 out of 10, Exceptional, (2 reviews)
"Very beautiful property and friendly owners we had an awesome time staying here! "
United States
Angel P.
$293 nightly
The price is $321
May 12 - May 13
Total with taxes and fees
PrivateOakForest RanchFirepit, BBQ&FamilyRetreat

The Gathering Place

The Gathering Place
2.0 star property
Kissimmee
5.0 out of 10, (2 reviews)
"clean room and bathroom"
United States
Matthew
$108 nightly
The price is $123
May 19 - May 20
Total with taxes and fees
The Gathering Place

Styled Bedrooms in a Resort

Styled Bedrooms in a Resort
2.0 star property
Solterra Resort
4.6 out of 10, (4 reviews)
"I was very comfortable with the people that were staying there. Very nice place. Would recommend anyone to stay."
United States
Jason
$104 nightly
The price is $116
Apr 29 - Apr 30
Total with taxes and fees
Styled Bedrooms in a Resort

Oakland Manor House

Oakland Manor House
3.0 star property
Oakland
$898 nightly
The price is $1,010
Apr 29 - Apr 30
Total with taxes and fees
Oakland Manor House
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Windermere Hotel Reviews

Find out more about Windermere

Windermere B&B information

Number of reviews
182
Accommodation
27 B&B
Lowest Price
$116
Highest Price
$1,010

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 $116 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