Where to stay in Winter Park, Orlando

Question

What Accommodations are there in Winter Park, Orlando

Answer

Winter Park is one of the most charming and upscale areas in the Orlando region, known for its tree-lined streets, brick-paved avenues, museums, lakes, restaurants, and the famous Park Avenue shopping and dining district. While it’s not packed with large hotels like the tourist corridor areas, it does offer a curated selection of boutique hotels, luxury stays, and nearby options that keep you close to the heart of Winter Park’s attractions.

Below is a detailed breakdown of the main accommodation options in and around Winter Park:

Hotels Located Directly in Winter Park

These are the most convenient choices if you want to be within easy walking distance of Park Avenue shops, restaurants, the Morse Museum, and Rollins College.

The Alfond Inn at Rollins College – The premier hotel in Winter Park. Upscale boutique property with beautiful art displays, refined rooms, a rooftop pool (after the current expansion), and an unbeatable location steps from Park Avenue. Perfect for a classic Winter Park experience.
Park Plaza Hotel – Historic boutique hotel right on Park Avenue. Rooms are charming with a European feel, some featuring wrought-iron balconies overlooking the avenue. Great if you want a cozy, walk-everywhere stay.
Hilton Garden Inn Winter Park – A modern hotel option just minutes from Park Avenue. Comfortable, reliable, and excellent for travelers who want something newer but still close to the action.

Hotels Very Close to Winter Park (5–10 minutes away)

If the Winter Park hotels are booked or you want more mainstream options, nearby areas like Maitland or North Orlando offer great hotels right on the city’s edge.

Homewood Suites by Hilton Orlando-Maitland – Spacious suites with kitchenettes, free breakfast, and a short drive into Winter Park. Good for longer stays.
Sheraton Orlando North (Maitland) – Large full-service hotel with a big atrium lobby. Convenient and comfortable, with easy access to I-4.
Residence Inn Orlando Downtown – A good choice if you prefer to stay between Winter Park and Downtown Orlando. Offers suite-style rooms and modern amenities.

Boutique Inns & Specialty Lodging

For travelers seeking a quieter or more unique Winter Park experience, these smaller inns or B&B-style stays offer charm and personality.

Thurston House Bed & Breakfast – A peaceful historic B&B just minutes from Winter Park, set on beautiful grounds overlooking Lake Eulalia. Ideal for a relaxing, romantic stay.
The Dr. Phillips House (Downtown/Sodo Area) – Not in Winter Park but a charming historic inn nearby, often chosen by visitors wanting character and uniqueness with quick access to Winter Park by car.
Local Vacation Rentals & Guesthouses – Winter Park has a selection of private cottages, carriage houses, and studios, especially near Lake Osceola and around the Rollins College area.

Tips for Choosing the Best Area in Winter Park

If your focus is on dining, art museums, and walkability, staying close to Park Avenue is the ideal choice. If you prefer more space, easier parking, or lower rates, look just outside the city in Maitland or North Orlando — you’ll still be only 5–10 minutes from the Winter Park highlights.

Where to stay in Winter Park, Orlando

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