Ocean City in the winter is gives that cozy laid back vibe.. No crowds and so many cute things to do with your friends. If you’re planning a girls’ weekend that’s equal parts relaxing, fun, and lowkey unhinged (in the best way), here’s how to do Ocean City, Maryland — winter edition.
Where We Stayed (and Stayed In for Dinner)
- First things first: accommodations. We stayed at DoubleTree by Hilton and Hyatt Place, and honestly? 10/10. Both have kitchenettes, which is so nice because it means you can hit the grocery store, cook dinner in matching pajamas, and save money for shopping and desserts (priorities). Everything you need, comfy beds, and perfect for late-night chats…and perhaps a few glasses of wine.
- The Grande is also located right on the boardwalk and is offering a $64 night stay or free upgrades! Click here to find out your options.
Self-Care but Make It Cute
- We kicked off the weekend with some serious self-care at Tifferson’s. If you’ve never done a head spa before… add it to your bucket list immediately. So relaxing, so aesthetic, and your hair feels unreal after. They also offer sugar cookie and peppermint mocha facials!
- Need a fun workout that doesn’t feel like punishment? We hit The Stoke with @ohthattierney for Pilates and yoga. It’s such a good vibe — great music, great energy, and you feel accomplished enough to fully justify a coffee and sweet treat afterward (as you should).
Coffee Runs & Boardwalk Walks (But Still Sleeping In)
- Winter mornings in OC = coffee in hand, walking the boardwalk, romanticizing life. We grabbed coffee from Java Beach Café at The Grande, and also stopped at Bai Tee on 14th Street for freshly baked treats. I highly recommend the home made chocolate chip cookie!
- After that, we bundled up and walked the boardwalk — so peaceful in the winter. No crowds, just ocean views, quality catch-up time, and of course the decadent smell of caramel popcorn.
- Feeling extra? Rent a surrey and cruise the boardwalk. Yes, it’s a little silly. Yes, people will stare. No, you will not care because it’s actually so fun.
Shopping (Obviously)
We did some damage shopping — in the best way.
- Park Place Jewelers for something sparkly and timeless
- Outlet shopping because deals = happiness
- Matching PJs from Old Navy or J.Crew (non-negotiable)
- HomeGoods & Marshalls because who doesn’t need another candle and a throw blanket?
- Ulta- Because…all the make up!
- For boutique shopping, @pattyjeansoceancity is a must — super cute pieces you won’t find everywhere. And for a forever souvenir, we got permanent jewelry with @shopkaistone. Such a fun girls’ activity and a cute reminder of the weekend.
Food, Wine & Sweet Treats- And a New Outfit
- Dinner at Spain Wine Bar was a VIBE. Amazing food, great wine, and perfect for a cozy but elevated girls’ night out in our dressy outfits.
- Dessert? Liquid Assets, obviously. Because life is short and dessert is mandatory. And their ice cream sandwich with homemade donuts and caramel is dreamy! We ate it too fast for a photo.
- One night we stayed in, cooked dinner at the hotel (thanks kitchenette), wore our matching PJs, and watched movies — honestly one of the best parts of the trip.
- We also caught a movie at Flagship Cinemas because let’s be honest, we’re all tired of our kids shows on repeat.
- And for breakfast, Oceans 13 breakfast boards are elite. The charcuterie style board included pancakes, fruit, bacon, sausage, and potatoes that you will absolutely be posting onto socials. We also ordered their mimosa flight because we could!
- Another option for dinner is the highly sought after roof op restaurant, Vista Roof Top. Offering stellar cocktails and a view that’s unmatched.
Nightlife & Just-for-Fun Moments
- If you want a casual night out, head downtown to Pickles Pub. Pool tables, live music, fun energy — no pressure, just a good time. They’re open 365 days a year!
- And if you really want to lean into the chaos… get old-time photos done. Trust me. You will laugh, you will cringe, and you will have the funniest keepsake forever.
Final Thoughts
Winter Ocean City is cozy, underrated, and literally perfect for a girls’ weekend. Between spa days, Pilates, shopping, wine bars, boardwalk walks, and staying in cooking dinner together, it’s the kind of trip that fills your cup without draining your bank account.
If you’re looking for a sign to plan a winter girls’ getaway — this is it.
