Find a Bed and Breakfast in Winter Park from CA $221

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Check prices for these dates

Next weekend
Aug 29 - Aug 31
In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19

Browse Select Winter Park B&B

Oakland Manor House
Staircase

Oakland Manor House

3.0 star property
Oakland Manor House
The Tiny Cottage in The Springs
Design Room | Living area

The Tiny Cottage in The Springs

4.0 star property
9.8 out of 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."
The price is CA $221
CA $939 total
includes taxes & fees
Aug 31 - Sep 1
The Tiny Cottage in The Springs
Luxury Home Near Disney sleeps 20
Outdoor pool, a heated pool

Luxury Home Near Disney sleeps 20

10.0 out of 10, Exceptional, (1)
"We all enjoyed the space & comfort of the house. Beds and linens were very comfortable with plenty of seating area for a large group. Neighborhood was very quiet and pool area was great for relaxing in the evenings when the sun went down. Our golfers loved the four golf courses near by. Owner was readily available (though we had no issues). We were enjoying spending time with our family so didn’t really make use of the movie room or the huge TV. Recommended for large groups."
Luxury Home Near Disney sleeps 20
Chilled Spot the perfect hide away.
Interior

Chilled Spot the perfect hide away.

10.0 out of 10, Exceptional, (3)
"We had a great time and the home was perfect for my family !!! Highly recommend!"
Chilled Spot the perfect hide away.
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 Winter Park Hotel Reviews

Rosen Inn at Pointe Orlando

Rosen Inn at Pointe Orlando

10/10 Excellent
"It was truly wonderful, the staff was so friendly and helpful that made my want to stay longer than I planned. "
Judith 2-night trip
Posted 7 hours ago
Rosen Inn at Pointe Orlando

Frequently asked questions

What is the nightly rate for a Bed & Breakfast in Winter Park?
Prices for B&Bs in Winter Park often vary, but you can find a great deal from CA $221 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Winter Park 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.
What is the difference between a Winter Park Bed and Breakfast and a hotel?
Every Winter Park 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 Winter Park B&Bs.