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Compare 7 B&B in Winter Park with updated reviews, rates, and availability.

Edgewater Hotel

2.5 star property
9.6 out of 10, Exceptional, (304)
"Nice place , good breakfast"
The price is $173
includes taxes & fees
$153 per night
Jun 1 - Jun 2
Edgewater Hotel

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 $669
includes taxes & fees
$651 per night
May 3 - May 4
The Tiny Cottage in The Springs

Luxury Home Near Disney sleep 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 sleep 20

Room in UCF area. Stay with Hugo and Marli, 68/ngt or 1.100/ monthly.

10.0 out of 10, Exceptional, (9)
"Quaint little room in a nice house. Hosts were very kind and hospitable, and it was very very clean. "
The price is $97
includes taxes & fees
$88 per night
May 7 - May 8
Room in UCF area. Stay with Hugo and Marli, 68/ngt or 1.100/ monthly.

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.

Oakland Manor House

2.0 star property
The price is $703
includes taxes & fees
$625 per night
May 8 - May 9
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.
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Other property types in Winter Park

Lake Buena Vista Resort Village & Spa

4.0 star property
8.4 out of 10, Very Good, (8644)
"Great family spot"
The price is $191
includes taxes & fees
$169 per night
May 7 - May 8
Lake Buena Vista Resort Village & Spa

Florida Hotel & Conference Center in the Florida Mall

3.5 star property
9.0 out of 10, Wonderful, (1892)
"Great spot and very comfy beds "
The price is $192
includes taxes & fees
$171 per night
May 16 - May 17
Florida Hotel & Conference Center in the Florida Mall

The View Studio Suites and Event Venue

3.0 star property
8.4 out of 10, Very Good, (1037)
"Very nice place to stay, with free breakfast "
The price is $77
includes taxes & fees
$69 per night
May 4 - May 5
The View Studio Suites and Event Venue
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.

Frequently asked questions

What is the nightly rate for a Bed and Breakfast in Winter Park?
Prices for B&Bs in Winter Park often vary, but you can find a great deal from $97 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.
When is the best time to book a Bed & Breakfast in Winter Park?
The best time to book a B&B in Winter Park is during the vibrant winter months from January to March, when the area transforms into a snowy paradise for outdoor enthusiasts. This peak season draws skiers and snowboarders from all over, eager to carve their paths on the pristine slopes of Winter Park Resort. With average temperatures ranging from the low 20s to mid-30s Fahrenheit, the crisp mountain air is invigorating, making it great for a day full of outdoor activities.

February, in particular, stands out as the most popular month, offering a festive atmosphere with numerous events and plenty of fresh powder. During this time, you can enjoy not only skiing but also snowshoeing and snowmobiling, all while surrounded by the stunning Rocky Mountain scenery. The lively après-ski scene adds to the experience, making it an excellent choice for those looking to unwind after an active day.

For travelers seeking a more budget-friendly option, consider visiting in early May. During this shoulder season, you can enjoy the beauty of the mountains as the snow begins to melt and flowers start to bloom. It’s a quieter time, great for exploring local trails and soaking in the serene landscapes without the crowds.
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.