Hotels in Winter Park (Florida, USA)

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162 hotels in Winter Park

  1. The Alfond Inn

    4 Stars
    Walkable access to Winter Park
    See prices from 20 sites
    from$404

  2. Park Plaza Hotel Orlando - Winter Park

    3 Stars
    Historic 1922 boutique hotel architecture
    See prices from 15 sites
    from$265

  3. SpringHill Suites by Marriott Winter Park

    3 Stars
    24-Hour Fitness Center Access
    See prices from 12 sites
    from$305

  4. Hilton Garden Inn Winter Park

    3 Stars
    Garden Grille restaurant and bar
    See prices from 13 sites
    from$323

  5. 1br 1ba In Historic Park Ave Home

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  6. Spacious Modern Japandi Retreat - Winter Park

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  7. Comfy Home In Winter Park, Can Accommodate Up 6 Guests!

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  8. Comfy Tiny Home WP Large Private Deck Queen bed

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  9. Charming home wp. Patio +Gazebo. close to highwys, park ave and downtown Orlando

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  10. Park Inn Orlando Winter Park

    3 Stars
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  11. Cute 5-bedroom house in peaceful Winter Park

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  12. Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow

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  13. Modern Elegance In The Heart Of Winter Park

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  14. Quaint Winter Park East End Market Home

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  15. Quaint Key West Pool Home

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  16. Florida Vacation Rental about 6 Mi to Downtown Orlando

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  17. Charming 2br/2ba Winter Park Cottage, Steps From Park Ave

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  18. Winter Park Lux 1 Bedrm 15 Mins From Downtown Orlando

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  19. Little Gem Apartment

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  20. Beautiful Mid Term Home In The Elegance Of Winter Park!nn

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  21. The Beautiful Melrose Cottage

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  22. Family Fun 3-bedroom house with gym, games, toys, outdoor hangout and coffee

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  23. Stylish 3BR/2BA Home in Lake View Retreat, near to Park,Trails,Pickleball,Golf.

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  24. Mills House @WP. Sleeps 11 Renovated. Queen beds

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  25. 5/4 King bed LUX Arcade near WP/CP & DT Orlando

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  26. Modern 3BR/3BA home in Prime Winter Park Location

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  27. 5-bedroom,6bed house in superb Winter Park

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  28. Cozy home 5min to Park Ave and Downtown Orlando, shopping, food and much more

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  29. Funky Remodeled Otown Bungalow Sleeps 8

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  30. Newly Remodeled Cottage

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  31. 3b/2ba Winter Park Residence w Music Studio & Office

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  32. Resort Like Winter Park Pool Home

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  33. Winter Park Spacious Unit - 118

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  34. Fantastic, quiet home minutes from Park Ave.

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  35. Enjoyable and cozy 1-bedroom apartment with AC in Winter Park

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The prices and availability we receive from booking sites change constantly. This means you may not always find the exact same offer you saw on trivago when you land on the booking site.

Other stays in Winter Park

Popular hotel categories in Winter Park

When to book a hotel in Winter Park

  • Cheapest month: March
    $328 per night
  • Yearly typical price
    $393 per night
  • Peak month: February
    $439 per night

Frequently Asked Questions about Winter Park

  • When is the cheapest time to book a hotel in Winter Park?

    March is usually the cheapest month to book a hotel in Winter Park, with typical prices around $328 per night based on 35 price comparisons.

  • When are hotel prices highest in Winter Park?

    Hotel prices in Winter Park are usually highest during February, with typical prices around $439 per night.

  • How much does a hotel in Winter Park cost per night?

    Hotel prices in Winter Park usually range from $295 per night to $467 per night, with typical prices around $393 per night.

  • How do hotel prices in Winter Park change throughout the year?

    Hotel prices in Winter Park are typically lowest in March at around $328 per night, rising to around $439 per night in February.

  • November

    2026

    $393
    $310 — $485

  • December

    2026

    $376
    $326 — $439

  • January

    2027

    $343
    $307 — $424

  • February

    2027

    $439
    $436 — $467

  • March

    2027

    $328
    $295 — $397

  • April

    2027

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  • May

    2027

    $426
    $419 — $442

  • June

    2027

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  • July

    2027

    $414
    $408 — $475

  • August

    2027

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  • September

    2027

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  • October

    2027

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Frequently Asked Questions about Winter Park

Hotels in Winter Park

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