Find Boutique Hotels in Winter Park, FL

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Winter Park Boutique Hotels

Tonight
3 Dec - 4 Dec
Tomorrow
4 Dec - 5 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Winter Park Boutique Hotels

Exterior
The Alfond Inn

The Alfond Inn

4.0 star property
Winter Park
9.6 out of 10, Exceptional, (1000)
"Amazing location, warm and friendly staff, beautiful property!"
Canada
Diandra
The Alfond Inn
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

Hyatt Regency Orlando

Hyatt Regency Orlando

10/10 Excellent
"the room was very clean, safe walkable area. Descend 21 is quite overpriced but expected for hotel restaurant. "
Nia 1-night trip
Posted 7 days ago
Hyatt Regency Orlando

Explore a world of travel with Expedia

Frequently asked questions

What's the best boutique-style hotel in Winter Park?
The Alfond Inn is a favorite hotel with Expedia travelers looking for a stylish stay, and features spa services and massages.
What's there to see and do in Winter Park?
The shopping and restaurants are just some of the things to enjoy while you're in the area. While you're out and about in Winter Park, popular attractions like Universal Studios Florida, Universal Orlando Resort, and Walt Disney World® Resort are worth a visit. You might also want to see well-known spots like Kia Center, Camping World Stadium, and Orlando International Premium Outlets during your trip.
What kind of weather should I plan for when I travel to Winter Park?
Getting an idea of what to expect from the weather in Winter Park is important when you plan your trip. The hottest months are usually July and August with an average temp of 82°F, while the coldest months are January and February with an average of 64°F. The rainiest months in Winter Park are August, September, July, and June, with each month seeing an average of 7 inches of rainfall.
What's the best way to get to my boutique hotel in Winter Park?
You have a few options for transportation to and around Winter Park. The nearest major airport is Orlando Intl. Airport (MCO), which is located 11.8 mi (19 km) from the heart of the city. If you want to explore the larger area, hop aboard a train at Winter Park Station.