Book Windermere Bed & Breakfast

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Check prices for these dates

Next weekend
Nov 14 - Nov 16
In two weeks
Nov 21 - Nov 23
In one month
Dec 5 - Dec 7
In two months
Jan 2 - Jan 4

B&B in Windermere

Porch
Kapp and Kappy B&B

Kapp and Kappy B&B

3.5 star property
Historic Downtown Kissimmee
9.8 out of 10, Exceptional, (124)
"Only B&B in Kissimmee. Owners were excellent. Enjoyed talking to them each morning over a great breakfast. Would definitely go back. "
United States
John
$130 nightly
The price is $148
Nov 9 - Nov 10
Total with taxes and fees
Kapp and Kappy B&B
Design Room | Living area | 40-inch Smart TV with digital channels, TV
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)
"Stay was amazing. Cozy and beautiful for a couple. Albia was easy to reach and very informing on the cottage and things in the area.. will definitely stay here again. "
United States
Luis
$678 nightly
The price is $699
Nov 11 - Nov 12
Total with taxes and fees
The Tiny Cottage in The Springs
Outdoor pool
Styled Bedrooms in a Resort

Styled Bedrooms in a Resort

2.0 star property
Solterra Resort
4.0 out of 10, (1)
"The room wasn't clean and the sink was clogged, there was no way to control the temperature in the room, very disappointed "
United States
Oscar E
$104 nightly
The price is $117
Dec 1 - Dec 2
Total with taxes and fees
Styled Bedrooms in a Resort
Outdoor pool
Hotel Styled Bedrooms in a Villa

Hotel Styled Bedrooms in a Villa

3.0 star property
Kissimmee
6.0 out of 10, (6)
"The house was dirty when I went there, the bed was a mess people was already sleeping in the room, the bathroom was filthy could even bathe in there nutty rags in the bathroom and the tub was dirty, I was offered another room that was a little better, I pulled up to the house to take my kids out the cat and to take out the bags and in less than 15 min someone towed my car, while it was still on key still in the car flashers on and everything, don’t even think of just pulling up just go park and...
United States
Phillojay
$119 nightly
The price is $136
Nov 8 - Nov 9
Total with taxes and fees
Hotel Styled Bedrooms in a Villa
Pool
Condo at Lake Buena Vista Village Resort and Spa

Condo at Lake Buena Vista Village Resort and Spa

2.0 star property
Orlando
$254 nightly
The price is $254
Nov 11 - Nov 12
Total with taxes and fees
Condo at Lake Buena Vista Village Resort and Spa
Shared kitchen
The Gathering Place

The Gathering Place

2.0 star property
Kissimmee
2.0 out of 10, (1)
"Not to clean or to friendly "
United States
Tier
The Gathering Place
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.
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Top Windermere Hotel Reviews

Hyatt Regency Orlando

Hyatt Regency Orlando

10/10 Excellent
"Great, over-sized room...front desk, valet & bell service outstanding...conveniently located"
Ronald Ray 3-night trip
Posted 15 hours ago
Hyatt Regency Orlando

Find out more about Windermere

Windermere B&B information

Number of reviews
132
Accommodation
12 B&B
Lowest Price
$117
Highest Price
$699

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 $117 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.

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