Oreo-Stuffed Hostess Cupcake Cookies – Easy Dessert Lovers’ Favorite

Let me set the scene: you open the oven door and a rush of chocolatey, sweet vanilla aroma hits you smack in the face. The smell is almost sinful, like you’ve just walked into an old-school bakery—frosting, melted chocolate, and yes, a hint of Oreo. The first time I made these Oreo-Stuffed Hostess Cupcake Cookies, I was knee-high to a grasshopper, helping my grandma at her kitchen table with a bowl bigger than my head. She’d let me sneak an extra Oreo now and then (okay, more than “now and then”), and honestly, those afternoons are still some of my favorite memories.

I remember biting into one fresh out of the oven. The cookie was still warm, the Oreo inside had gone a bit gooey, and the frosting on top was just barely set—pure, nostalgic comfort. I paused, took a deep breath, and grinned because you know what? I knew I’d stumbled onto something truly special. These cookies combine the best of both worlds: the classic Hostess cupcake vibe and the irresistible crunch of Oreo in every bite.

My family couldn’t stop sneaking them off the cooling rack (and I can’t really blame them). Even my uncle, who claims he “doesn’t do sweets,” ate three in one sitting. They’ve been a staple for birthday parties, gifting, and—let’s face it—those days when you just need a pick-me-up. Honestly, I wish I’d discovered this Oreo-Stuffed Hostess Cupcake Cookie recipe years ago for school bake sales or potlucks. It’s dangerously easy, fits right in with Pinterest-worthy dessert boards, and feels like a warm hug wrapped in chocolate and nostalgia. I’ve tested and tweaked this recipe more times than I care to admit (in the name of research, of course!), and each time, it reminds me why these cookies are a must for dessert lovers. You’re going to want to bookmark this one!

Why You’ll Love This Oreo-Stuffed Hostess Cupcake Cookie Recipe

There’s a reason these decadent Oreo-Stuffed Hostess Cupcake Cookies have become my go-to dessert for nearly every occasion. I’ve baked countless batches—sometimes just for the joy of it, sometimes for family gatherings, and once for a friend’s birthday party where they disappeared so fast I barely snagged one for myself. Here’s why they stand out from the crowd:

• Quick & Easy: Comes together in under 45 minutes, so you’re not stuck in the kitchen all afternoon. Perfect for that last-minute sweet tooth attack.
• Simple Ingredients: No fancy grocery trips required. You probably have everything already—Oreos, basic cookie dough staples, and Hostess cupcake essentials.
• Perfect for Any Occasion: Whether it’s a kid’s birthday party, a grown-up potluck, or just a Tuesday night treat (no judgment), these cookies fit right in.
• Crowd-Pleaser: Trust me, adults and kids alike will fight over the last one. The Oreo surprise in the middle gets rave reviews every time.
• Unbelievably Delicious: The combination of soft cookie, creamy filling, and crunchy Oreo is next-level comfort food—there’s just nothing else like it.

What makes this Oreo-Stuffed Hostess Cupcake Cookie recipe really different? For starters, the filling is made with a blend of marshmallow cream and a touch of vanilla, so it’s ultra-smooth (like a Hostess cupcake, but even better). Instead of just plopping an Oreo on top, you get that dramatic, gooey Oreo center with every bite. The cookie dough itself is rich but not too sweet, so it balances perfectly with the Oreo and frosting.

Honestly, this isn’t just another cookie—it’s the kind you close your eyes after that first bite and think, “Yup, this is worth every single calorie.” It’s comfort food made faster and easier, but with all the soul-soothing satisfaction you crave. I love that it impresses guests with almost zero stress. Just whip up the dough, stuff in the Oreos, and boom—you’ve got a dessert that’s as memorable as it is delicious. If you’re after a dessert that makes people pause and savor, this is the one.

What Ingredients You Will Need

This recipe uses simple, wholesome ingredients to deliver bold flavor and satisfying texture without the fuss. Most are pantry staples, so you probably won’t need a special trip to the store. Here’s what you’ll need for Oreo-Stuffed Hostess Cupcake Cookies:

• For the Cookie Dough:
  • 2 1/4 cups (280g) all-purpose flour
  • 1/2 cup (45g) unsweetened cocoa powder (for that Hostess cupcake flavor)
  • 1 tsp baking soda
  • 1/2 tsp salt
  • 1 cup (226g) unsalted butter, softened (adds richness)
  • 1 cup (200g) granulated sugar
  • 1/2 cup (100g) brown sugar, packed (for chewiness)
  • 2 large eggs, room temperature
  • 2 tsp pure vanilla extract (I like Nielsen-Massey)
• For the Oreo Stuffing:
  • 18 classic Oreo cookies (plus more if you’re a snacker)
• For the Hostess Cupcake Filling:
  • 3/4 cup (170g) marshmallow cream
  • 2 tbsp (30g) unsalted butter, softened
  • 1/2 tsp pure vanilla extract
  • 1/2 cup (60g) powdered sugar
  • Pinch of salt
• For the Chocolate Frosting:
  • 1 cup (175g) semisweet chocolate chips
  • 3 tbsp (42g) unsalted butter
  • 2 tbsp (30g) heavy cream (use milk if needed)
  • 1/2 cup (60g) powdered sugar
• Optional Decoration:
  • White icing gel or melted white chocolate (for classic Hostess swirl)
  • Sprinkles (for a fun twist)

Ingredient Tips: For best results, use firm, fresh Oreos (stale ones can get mushy). If you’re gluten-free, swap the flour for a 1:1 gluten-free blend and use gluten-free sandwich cookies. For dairy-free, swap butter for vegan margarine and use coconut cream instead of heavy cream.

Brand Note: I prefer Ghirardelli chocolate chips for the frosting—they melt super smooth. For marshmallow cream, Jet-Puffed is my go-to, but homemade works, too!

Seasonal twist? In summer, try Golden Oreos for a lighter flavor, or mix in crushed peppermint for holiday cookies. The ingredients are flexible enough to let you get creative without losing that Hostess magic.

Equipment Needed

• Large mixing bowl (a must for combining dough—my grandma always used a big ceramic one)
• Electric mixer or stand mixer (makes creaming butter and sugar a breeze)
• Medium bowl (for frosting and filling)
• Rubber spatula (for scraping every last bit—trust me, you’ll want it)
• Baking sheet (standard size, lined with parchment for easy cleanup)
• Small cookie scoop or tablespoon (for portioning dough evenly)
• Wire cooling rack (crucial for setting cookies so they don’t get soggy)
• Microwave-safe bowl (for melting chocolate chips, unless you prefer a double boiler)
• Piping bag or zip-top bag (optional, for decorating with the Hostess swirl)

If you don’t have a stand mixer, a sturdy hand mixer works just fine. I’ve made these with nothing but a wooden spoon when camping (you just need a little elbow grease!). For decorating, a zip-top sandwich bag with a snipped corner is a cheap substitute for fancy piping bags.

Maintenance tip: Wipe your wire cooling rack right away—chocolate frosting can stick if you wait too long. Parchment paper is your best friend for keeping baking sheets clean and getting those cookies off with zero fuss.

Budget-friendly? Absolutely. Most of these tools are already in your kitchen or easy to find at any discount store. No need for specialty equipment—just keep it simple.

Preparation Method

1. Prep the Oven and Ingredients:
   
   Preheat oven to 350°F (175°C). Line your baking sheet with parchment paper. Set out all ingredients to reach room temperature—especially the butter, eggs, and marshmallow cream.
   
   Tip: Room temp ingredients blend smoother and give you fluffier cookies.
2. Make the Cookie Dough:
   
   In a large bowl, whisk together flour, cocoa powder, baking soda, and salt. In another bowl, cream the butter, granulated sugar, and brown sugar together with an electric mixer until light and fluffy (about 2–3 minutes).
   
   Beat in eggs one at a time, then mix in vanilla extract.
   
   Gradually add the dry ingredients to the wet, mixing until just combined.
   
   Sensory cue: Dough will be soft but not sticky. If it’s too sticky, pop it in the fridge for 10 minutes.
3. Prepare the Filling:
   
   In a medium bowl, beat together marshmallow cream, butter, vanilla, powdered sugar, and a pinch of salt until fluffy (about 1 minute).
   
   Tip: Don’t overmix or the filling can get runny.
4. Assemble the Cookies:
   
   Using a cookie scoop or tablespoon, scoop a ball of dough (about 2 tablespoons/30g). Flatten slightly, place an Oreo in the center, and top with a small spoonful of filling (roughly 1 teaspoon/5g).
   
   Cover with another scoop of dough, sealing edges so Oreo and filling are hidden.
   
   Troubleshooting: If dough tears, wet fingers lightly to patch seams.
5. Bake:
   
   Arrange cookies 2 inches (5cm) apart on the prepared sheet. Bake for 12–14 minutes, until edges are set but centers are slightly soft.
   
   Sensory cue: Cookies will look crackly on top and smell intensely chocolatey.
   
   Let cool on baking sheet for 5 minutes, then transfer to a wire rack.
   
   Warning: Don’t move them too soon—they’re fragile when hot!
6. Make the Frosting:
   
   In a microwave-safe bowl, melt chocolate chips and butter in 30-second bursts, stirring each time until smooth. Stir in heavy cream and powdered sugar until glossy.
   
   Tip: If frosting is too thick, add more cream by the teaspoon.
7. Decorate:
   
   Once cookies are cool, spread a layer of frosting on each. Pipe a classic Hostess swirl using white icing gel or melted white chocolate.
   
   Add sprinkles if you’re feeling festive.
   
   Efficiency tip: Use a zip-top bag for piping if you don’t have a piping bag.
8. Serve:
   
   Let the frosting set for 15 minutes before serving (if you can wait!). Cookies are best enjoyed fresh but keep well for a few days.
   
   Note: The Oreo center will be soft and gooey right after baking—total magic!

Cooking Tips & Techniques

I’ve made more batches of these Oreo-Stuffed Hostess Cupcake Cookies than I can count, and I’ve learned a few tricks along the way. Here’s what I wish someone had told me:

• Chill the dough if it’s too soft: Ten minutes in the fridge makes shaping way easier and prevents spreading.
• Stuffing technique: Hold the dough in your palm and press the Oreo gently, then pinch the edges closed. Don’t worry about perfection—cracks are fine and add a rustic look.
• Don’t overbake: The cookies should look slightly underdone in the center. They firm up as they cool, and if you bake until fully set, you’ll lose that soft, Hostess-cupcake-like texture.
• Frosting consistency: If your frosting seizes (gets grainy), add a splash of cream and whisk vigorously. I’ve ruined a batch or two by overheating the chocolate, so go slow!
• Multitasking: While cookies bake, whip up the filling and frosting to save time. If you’re making a big batch, set up a cookie assembly line—my kids love helping with the stuffing.
• Consistency matters: Use a cookie scoop for even sizes so they bake at the same rate. Uneven cookies can lead to raw centers or burnt edges.

Common mistakes? I’ve made them all—forgetting to seal the edges so the filling leaks, moving cookies too soon, or skipping the parchment paper (hello, cookie carnage). With practice, you’ll get the hang of it. Honestly, a little mess just means you’re having fun.

Variations & Adaptations

The beauty of these Oreo-Stuffed Hostess Cupcake Cookies is how easily you can customize them. Here are some of my favorite twists:

• Dietary Variation: For gluten-free, swap the flour for a 1:1 gluten-free baking mix and use gluten-free sandwich cookies. For dairy-free, use vegan butter and coconut cream instead of heavy cream.
• Seasonal Twist: Try peppermint-filled Oreos for the holidays, or lemon Oreos for a springtime treat. I once tossed in crushed candy canes for a festive crunch—huge hit with the kids!
• Flavor Adaptation: Add a tablespoon of espresso powder to the dough for a mocha flavor, or substitute the vanilla extract with almond for a nutty twist.
• Cooking Method: Want mini cookies? Use half-size Oreos and reduce baking time by 2–3 minutes. For a deep-dish version, press dough into a muffin tin, stuff, and bake for 16–18 minutes.
• Allergen Substitutions: Nut-free? All ingredients here are naturally nut-free, but always check your brands. For egg-free, use a flaxseed egg (1 tbsp ground flax + 2.5 tbsp water).

My personal favorite? Swapping in peanut butter Oreos for an extra punch. It’s a game changer. Honestly, don’t be afraid to mix and match flavors—you might just stumble on your new family tradition.

Serving & Storage Suggestions

These decadent Oreo-Stuffed Hostess Cupcake Cookies are best served slightly warm so the Oreo center is gooey and the frosting is soft. Arrange them on a pretty platter for parties, or stack them in a cookie tin lined with wax paper for gifting. They pair beautifully with a cold glass of milk, hot coffee, or even a scoop of vanilla ice cream if you’re feeling extra indulgent.

For storing, keep cookies in an airtight container at room temperature for up to 4 days. If you want to freeze them, wrap each cookie in plastic wrap and freeze for up to 2 months. Let thaw at room temp before serving.

To reheat, pop a cookie in the microwave for 10–12 seconds (don’t overdo it—frosting melts fast). The flavors actually deepen after a day or two, so leftovers are almost better. If you want the Hostess swirl to stay pretty, refrigerate cookies after frosting for 20 minutes before stacking or storing.

Nutritional Information & Benefits

Each Oreo-Stuffed Hostess Cupcake Cookie clocks in at around 260 calories, with 12g fat, 35g carbohydrates, and 3g protein. They’re a definite treat, best enjoyed in moderation. Key ingredients like cocoa powder and eggs bring a boost of antioxidants and protein, while marshmallow cream keeps things light and fluffy.

For those watching dietary needs, the recipe adapts easily to gluten-free or dairy-free. These cookies are nut-free, so safe for most school events. The main allergens are wheat, egg, dairy, and soy (from Oreos)—always check labels if serving to a crowd.

From a wellness perspective, I see these as a joyful indulgence. Sometimes, comfort food is what you need, and if you’re going to splurge, these cookies deliver all the satisfaction. Enjoy every bite!

Conclusion

To sum it up, Oreo-Stuffed Hostess Cupcake Cookies are the ultimate dessert for anyone who believes cookies should be fun, indulgent, and memorable. They’re shockingly easy, totally customizable, and packed with nostalgic flavor. Whether you’re baking for a crowd, giving homemade gifts, or just treating yourself, this recipe is a keeper.

Don’t be afraid to tweak the flavors and make them your own. My favorite part is sharing these with friends and family—seeing their faces light up after the first bite is what dessert is all about. If you love decadent, Pinterest-worthy cookies, you owe it to yourself to try this recipe.

Let me know how yours turn out in the comments below, or share your creative twists! I love seeing how everyone puts their own spin on these—so tag me if you post them on Instagram or Pinterest. Happy baking, dessert lovers!

Frequently Asked Questions About Oreo-Stuffed Hostess Cupcake Cookies

Can I make these Oreo-Stuffed Hostess Cupcake Cookies ahead of time?

Absolutely! You can bake them a day ahead and store in an airtight container. The flavors actually get even better after a night’s rest.

Can I freeze these cookies?

Yes, just wrap each cookie in plastic and freeze for up to 2 months. Thaw at room temperature before serving for best texture.

What’s the best way to stuff the cookies without them falling apart?

Use chilled dough and gently pinch the edges closed around the Oreo. Don’t stress about perfection—cracks add charm!

Can I use Double Stuf Oreos in the center?

You sure can! Just be aware the cookies will be even bigger and gooier—so maybe bake a minute longer.

Are there any nut or allergy concerns with this recipe?

The basic recipe is nut-free, but always check labels for cross-contamination. Main allergens are wheat, egg, dairy, and soy (from Oreos).

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