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The Best Hotels in Winter Park, Florida and Fun Things to Do

iStock-578089810.jpgWithin a half hour’s drive of Orlando to the south, and super-close to Full Sail University, Winter Park is a small town of suburban communities in Orange County.

Originally, the popular Florida city was founded as a home for upscale, resort communities, but the local arts scene and antique lovers have allowed the downtown district to become retro in the best way. There are sidewalks everywhere in downtown Winter Park, with small cafes and shops on either side.

Most of the attractions in Winter Park are either historic, outdoors, or both, so pack a good pair of sneakers for an afternoon of sights to see.  There are plenty of fun things to do in Winter Park, FL!


Rollins College on Holt Avenue gives you an up-close look at the local artworks, with exhibits of new installations from student artists. While the interior is perfect for art lovers, the exterior is a great place for nature lovers and history buffs. The grounds are well-kept with a touch of wild Spanish moss, and a nature path that leads to an old chapel with vintage stained glass windows.

Cornell Fine Arts Museum is a favoriiStock-583720904.jpgte in Winter Park, featuring thousands of artworks from centuries past. The exhibits are divided into eras, like modern art and Renaissance era masterpieces, each with a plaque to detail and give credit to artists and artwork facts. There are even a few temporary exhibits that change on a monthly basis to show praise and appreciation for local artists.

Lake Baldwin Park on Lakemont Avenue is a pet-friendly place, with over 23 acres of lakeside beaches, rentable pavilions, boat ramps, fishing docks, and nature trails. Head over during a weekday to avoid weekend crowds.

Though only a few lodging choices in the city, the best hotels in Winter Park are quite pleasant, comfortable, and outfitted with the best in modern comforts. According to TripAdvisor, the best hotel options in the area include The Alfond Inn, Park Plaza Hotel Winter Park, Quality Inn & Suites Winter Park Village, and Country Inn & Suites. 


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Which Winter Park hotel will you choose?


The Alfond Inn

The Alfond Inn, situated on East New England Avenue, has a TripAdvisor rank of number one hotel in Winter Park. The exterior is luxurious, gorgeous, and well-kept, while the interior is often described as akin to paradise. The vintage Florida hotel is large with over 100 rooms, but it is still considered a small boutique. And there are so many things to do and see that you never have to leave the resort to do and see things elsewhere [unless you want to]. Some of the attention-grabbing amenities include an on-site restaurant with a bar, lounge, and outdoor patio, a workout room with all-modern equipment, and a sparkling swimming pool.


The Park Plaza Hotel Winter Park

The Park Plaza Hotel - Winter Park sBeautiful woman eating her breakfast at home.jpegettled on South Park Avenue, is an old-fashioned boutique hotel that lies in Downtown Winter Park. There are 28 themed rooms, with antiques decorating the interiors. Often described as romantic, the hotel offers a plethora of nice amenities, such as free hot breakfasts, free high-speed internet, and laundry services. A concierge is available upon request, so you can work with a professional planner to plan out the entirety of your vacation.


The concierge will help you see all you want to see, while maintaining a budget that won’t break your bank. Park Plaza features beautiful ensuite balconies, each overlooking another section of rose gardens and a well-kept courtyard. Of course, since you are in downtown, you are close to all kinds of restaurants, shops, and activities. However, you should visit the Charles Hosmer Morse Museum of American Art when you have the chance. From stained glass artworks, to local masterpieces, the museum showcases Morse’s life works from one unique, beautiful exhibit to the next.



Quality Inn & Suites Winter Park Village

Couple having a drink at the bar and smiling.jpegAnother hotel favorite, located on Lee Road, is the Quality Inn & Suites Winter Park Village that features hospitable customer services and a number of accommodating amenities. For example, each room is equipped with basic essentials to make your stay homier and more comfortable. Some of these essentials include a microwave, counter space, an abundance of bathroom toiletries, and clean, fluffed towels whenever you need them. Get a flat-screen television with cable access, high-speed internet, and a well-furnished sitting area to relax in after a long afternoon of sight-seeing.


Other hotel accommodations include a swimming pool and hot tub, an on-site fitness center, a free daily breakfast, a business center with meeting rooms, and a banquet room for celebrations such as weddings, receptions, reunions, and mitzvahs


Less than 2 miles from the Quality Inn is Enzian Theatre, a place where you can enjoy dinner and a classic movie. For instance, the theatre showcased the anniversary edition of Dirty Dancing in the summer of 2017, with a chickpea salad, grilled cheese sandwiches, and kettle popcorn. A short walk from the theatre is the Eden Bar—a lounge area that serves up mixed drinks, light lunches, and homemade dinners.


Country Inn & Suites

bigstock-Young-couple-relaxing-in-hot-t-88606304.jpgPositioned on Lee Road, the Country Inn & Suites is an old-fashioned hotel with basic but modern amenities to accommodate a wide range of guests. Business professionals, families, honeymooners, and weekend vacationers have all experienced a positive stay here at one time or another—so says numerous online reviewers. This hotel offers the essentials in a simple, no frills atmosphere, but their customer service shines through as beyond courteous and knowledgeable.


The 200 rooms have suite layouts with size varying with guest needs. Basic hotel amenities include an outdoor swimming pool with a lounge area, free high-speed internet, free parking spots, self-serve laundry rooms, and extra towels and toiletries upon request. Rooms feature a plethora of accommodations, including but not limited to: a kitchen with a mini fridge and microwave, an air conditioning system, a well-furnished sitting area with a flat-screen television and cable access, one or two comfortable double beds, and a spacious, towel-stocked bathroom.


Overcome your fear of heights, or simply plan an adventure, with Via Air Tours. The booked luxurious plane takes you over Winter Park and Orlando to see attractions, like Disney World and the Magic Kingdom, from a new perspective.


Dine at Winter Park's top restaurants!


  • iStock-144273158.jpg4 Rivers Smokehouse - American, Barbecue, Vegetarian Friendly, Gluten Free 
  • Hillstone Restaurant - American, Vegetarian Friendly, Vegan, Gluten Free 
  • Tibby's New Orleans Kitchen Winter Park - American, Seafood, Cajun/Creole, Gluten Free 
  • Bosphorous Turkish Cuisine - Mediterranean, Greek, Middle Eastern, European
  • Luma - American, Vegetarian Friendly, Vegan, Gluten Free
  • Ethos Vegan Kitchen - American, Vegetarian Friendly, Vegan, Gluten Free
  • Prato - Italian, Pizza, Vegetarian Friendly, Gluten Free
  • Winter Park Fish Company - Seafood, American, Cajun/Creole, Gluten Free




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Topics: Florida