Winter Park(United States) Travel 2026: Cheap Flights, Hotels & Top Attractions

In Winter Park, top picks for families include The Drury Inn & Suites Orlando - Winter Park, located steps from Lake Howell and the historic downtown district. This hotel offers spacious family rooms, a free breakfast buffet, and an outdoor pool. Nearby attractions like the University of Florida and Orlando Science Center provide educational fun for kids. With easy access to both nature and culture, it's ideal for parents seeking comfort, convenience, and child-friendly amenities in a peaceful setting.

The downtown Winter Park district is the prime area for accommodation. It features charming Victorian architecture, boutique shops, and acclaimed restaurants along Park Avenue. Stay at The Winter Park Resort or The Inn at Winter Park for proximity to Lake Osceola, art galleries, and cultural events. This neighborhood offers a tranquil escape from Orlando’s theme parks while delivering a refined, walkable urban experience with local character and upscale charm.

Don’t miss the Winter Park Art Festival, held annually in spring along Lake Osceola, showcasing over 200 artists from around the world. Another highlight is the Winter Park Playhouse, which stages classic musicals each season, reflecting the city’s deep-rooted theater tradition. Stroll through the Historic District to admire late-19th-century buildings, and explore local galleries and craft studios—perfect for immersing yourself in the city’s creative spirit and heritage.

For couples seeking romance, The Lodge at Winter Park stands out with its lakeside location on Lake Osceola, offering private balconies and panoramic views. The resort features candlelit dinner packages, complimentary wine upon arrival, and opportunities for paddleboarding at sunset. Evening walks along the City Walk path, illuminated by soft lights and surrounded by trees, create intimate moments. Ideal for rekindling love away from tourist crowds, this boutique retreat blends luxury and serenity perfectly.

Road-trippers should consider Holiday Inn Express & Suites Orlando - Winter Park, just a 15-minute drive from Disney World but nestled in a quiet residential area. The hotel provides free airport shuttles, spacious rooms with kitchenettes, and a complimentary breakfast. Nearby, the Winter Park Greenway offers scenic biking routes connecting to Florida State Botanical Garden, making it a perfect pit stop for travelers exploring Central Florida’s natural beauty and small-town charm.

Savor local flavors at Bread & Butter Bistro, known for its gourmet breakfast sandwiches and expertly brewed coffee. For a taste of Mediterranean flair, visit Café Moxie, a cozy café serving organic salads and handmade pastries. On Saturdays, head to the Winter Park Farmers Market to sample fresh produce, artisanal cheeses, and homemade jams—then enjoy a quick bite at a food cart. These culinary spots reflect the city’s emphasis on quality ingredients and community-driven dining.

Capture stunning shots at Lake Osceola, especially during sunrise when mist blankets the water and tall oaks frame the view. The colorful facades along Park Avenue Art Gallery District and public sculptures make for vibrant street photography. Don’t miss the Winter Park City Hall clock tower and rose garden, or the Gothic-style buildings on the University of Florida campus—ideal for architectural and historical photography. Each spot reflects the city’s blend of elegance and natural beauty.

Explore the Winter Park Greenway, a 4.5-kilometer paved trail linking Lake Osceola to the Florida State Botanical Garden. It’s perfect for cyclists and walkers, featuring shaded paths, rest stops, and abundant wildlife like herons and turtles. For a shorter hike, stroll the City Walk from downtown to the Art District, passing fountains, murals, and century-old trees. Both routes combine lush greenery with urban charm, offering a refreshing escape into nature without leaving the city.

Evenings in Winter Park shine with cultural offerings: catch a performance at the Winter Park Playhouse, a professional theater with live musicals. Take a moonlit walk along Lake Osceola, where illuminated fountains dance across the water. Enjoy craft cocktails at The Grove, a popular open-air bar with live music. Or unwind with a spa treatment at Spa at The Lodge, blending relaxation with serene lake views—perfect for ending a day in style.

To feel the pulse of Winter Park, join the weekly Winter Park Farmers Market every Saturday, where locals trade fresh produce, honey, and handmade crafts. Participate in guided tours hosted by the Winter Park Civic Association to uncover hidden stories behind historic buildings. Spend an afternoon browsing independent bookstores, ceramic studios, and neighborhood cafes along Park Avenue—where conversations flow as freely as the coffee. This is how real Floridians live: slowly, thoughtfully, and deeply connected to place.