Search Luxury Hotels in Winter Park

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Check availability on Winter Park Luxury Hotels

Tonight
30 Dec - 31 Dec
Tomorrow
31 Dec - 1 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Winter Park luxury hotels

Exterior
The Alfond Inn

The Alfond Inn

The Alfond Inn
4.0 star property
Winter Park
9.6 out of 10, Exceptional, (1008)
"Beautiful, classy hotel w/o breaking the bank. Pretty grounds and conveniently located."
United States
Craig
The Alfond Inn
Front of property
Park Plaza Hotel

Park Plaza Hotel

Park Plaza Hotel
3.0 star property
Park Avenue District
8.6 out of 10, Excellent, (1004)
"Would stay at the Park again."
United States
Edward
The price is ฿5,473
฿6,157 total
includes taxes & fees
23 Jan - 24 Jan 2026
Park Plaza Hotel
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

Top Winter Park Hotel Reviews

Universal's Cabana Bay Beach Resort

Universal's Cabana Bay Beach Resort

10/10 Excellent
"All great !"
Chong 8-night trip
Posted 17 hours ago
Universal's Cabana Bay Beach Resort

Frequently asked questions

Are you searching for a great accommodation for your luxury trip to Winter Park?
During your visit, you might want to enjoy the university which Winter Park is known for.
What's the best high-end place to stay in Winter Park?
The Alfond Inn is a luxury hotel with 2 outdoor pools and spa services, and it's a popular choice for Expedia travellers looking for an elegant place to stay.
When can I expect good weather in Winter Park?
Planning for the weather is an important factor for making your trip to Winter Park a success, especially when you're splurging. The hottest months are usually July and August, with an average temperature of 28°C, while the coldest months are January and February, with an average of 18°C. The rainiest months in Winter Park are August, September, July and June, with each month seeing an average of 185 mm of rainfall.
What's there to see and do in Winter Park?
When you're in Winter Park, enjoy exploring the sights and attractions here including Casa Feliz Historic Home Museum, Winter Park Village and Morse Museum of American Art. If you have some spare time during your trip, you might want to check out Kraft Azalea Gardens and Lake Virginia.
How can I get around Winter Park?
It's easier to get around town comfortably when you know your options. To see more of the larger area, hop aboard a train at Winter Park Station.