10 Holiday Trips Worth Your PTO, Based on Your OOO Vibe
Wellness

10 Holiday Trips Worth Your PTO, Based on Your OOO Vibe

This content was created by Girlboss in partnership with Hilton.

Sure, you could go back to your hometown for the holidays, where you’ll probably run into your high school ex at the local bar. *Shudders.* Or you could just… skip it entirely?

That’s right, we’re making the case for booking a holiday getaway instead. From an all-inclusive beach resort in Punta Cana to a cozy ski retreat in Park City, we rounded up 10 Girlboss editor-approved Hilton hotels worth using up your PTO for, no matter your OOO vibe.

P.S. Your aunt might be a little annoyed that you’re missing out on her world-famous mashed potatoes, but we think she’ll understand when you send a postcard from somewhere warm.

If you want an all-inclusive where you can turn your brain off…

A woman sitting on a lounge chair with her laptop in her lap at the Zemi Miches Punta Cana All-Inclusive Resort, Curio Collection by Hilton.

Zemi Miches Punta Cana All-Inclusive Resort, Curio Collection by Hilton

📍 Punta Cana

The lowdown: This Pinterest-worthy all-inclusive escape sits on the untouched shores of Miches, with four pools, an ancestral-inspired cave spa, and 17 restaurants, bars, and lounges. They even have beachside bungalows with private plunge pools if you want to go all out.

What to eat and drink: Make a reservation at Toa for Taíno-inspired Caribbean dishes, or at Boba if you’re craving Thai street food (the tuna tartar cone is a don’t-miss).

Don’t miss: Acana Spa & Wellness, a cave-inspired sanctuary built around a tranquil Ojo de Agua, which pays homage to Taíno heritage. Book the Opia Quartz Sand Massage, performed on a bed of warm quartz sand.

Good to know: The Club Azure upgrade comes with private check-in, a dedicated concierge, and lounge access. You’ll also get butler service, VIP airport transfer to and from Punta Cana Airport, and a 15% discount on spa massages. So worth the splurge!

If you want to spend the last few days of 2026 on island time…

An aerial view of Hilton Hawaiian Village Waikiki Beach Resort

Hilton Hawaiian Village Waikiki Beach Resort

📍 Waikiki Beach, HI

The lowdown: This 22-acre oceanfront resort sits on a wide stretch of Waikiki Beach, with multiple pools, waterslides, and a five-acre saltwater lagoon where you can try stand-up paddle yoga or ride an aquacycle.

What to eat and drink: Book dinner at Bali Oceanfront for mouthwatering island harvest cuisine with a dreamy view of Waikiki Beach. Order a tropical cocktail (Mai Tai, anyone?) at the Hau Tree Bar by the Super Pool, then swing by Chee Hoo Patisserie for French pastries and Dole Whip if you’ve still got room for dessert (duh).

Don’t miss: The Waikiki Starlight Luau, where you'll indulge in an island feast (like kalua pig!), and see an incredible dance show covering Samoan, Tahitian, and Hawaiian traditions, plus fire knife dancers. And every Friday, there’s a fireworks show!

Good to know: The resort has five towers, and the Kalia Adult Pool (18+) is a fully kid-free zone. If you’re traveling for Thanksgiving, the resort hosts a dinner at Bali Oceanfront and a buffet at Rainbow Lanai on November 26.

If you want back-to-back spa treatments and an overflowing glass of Cab Sauv...

A private terrace at the Casa Mani Resort Napa Valley, Curio Collection by Hilton.

Casa Mani Resort Napa Valley, Curio Collection by Hilton

📍 Napa, CA

The lowdown: This urban resort is the best of both worlds: it’s about a mile from downtown Napa and a short drive from the vineyards. Spend the day vineyard hopping, then wind down at either the resort-style pool, hot tub, or redwood-shaded lawn with firepits (pictured above).

What to eat and drink: Start with a glass at The Collective Wine Bar in the lobby lounge, where the pours come from Lawrence Wine Estates (and you get preferred access to estate tastings, hello, bougie!). Then reserve a table at BOA Steakhouse for dry-aged prime steaks by candlelight. Um, how romantic!

Don’t miss: The spa’s Hydrothermal Circuit, which has a sauna, a steam room, and a cold shower to reset your whole nervous system. Treat yourself to a massage, and you’ll get an hour of complimentary access beforehand. Bonus: phones aren’t allowed in the spa, so you’ve got the perfect excuse to unplug.

Good to know: This resort is in the city of Napa, about an hour north of San Francisco and Oakland and an hour west of Sacramento, which makes it an easy weekend escape. Bringing a pup? Rooms are pet-friendly, so your four-legged bestie can come along.

If you want to experience a classic Home Alone 2 holiday…

A view of the street from a hotel window at the New York Hilton Midtown.

New York Hilton Midtown

📍 New York City, NY

The lowdown: Is there anything more magical than Christmas in New York? This classic hotel is smack in the middle of all the festive action: opposite the Museum of Modern Art and two blocks from both Rockefeller Center and Radio City Music Hall. Catch the famous Christmas tree, then bundle up and walk down Fifth Avenue to see the lights and holiday windows.

What to eat and drink: You simply can’t go hungry in New York. Share pasta and tiramisu at Osteria La Baia, an Italian spot a block from the hotel that’s perfect for a post-skate refuel. Then head to Madame George (a cool cocktail lounge) for a nightcap.

Don’t miss: Radio City Music Hall’s Christmas Spectacular with the Rockettes. Then lace up your skates at the Rockefeller Center rink and pretend you’re in a Hallmark movie.

Good to know: Planning a Thanksgiving trip? The hotel is directly on the parade route, so you can book one of their private parade-view rooms (four- or five-night minimum stay required). Herb N’ Kitchen also hosts a Thanksgiving buffet feast with more than 20 dishes.

If you want to hit the slopes hard and aprés ski harder…

Canopy by Hilton Deer Valley

Canopy by Hilton Deer Valley

📍 Park City, UT

The lowdown: This newly built mountain hideaway in Deer Valley is made for ski and snowboard lovers alike. It has immediate access to the Jordanelle Express Gondola, so you’re never far from the slopes. Come home to an indoor pool, sauna, steam room, and fireplace lounge, because your legs will need it after a day on the hill.

What to eat and drink: Head up to Alpine Attic, the rooftop spot with soul-warming dishes, handcrafted cocktails, and breathtaking mountain views. Then carb-load at Tavolona, an Italian trattoria with homemade pastas and an impressive wine list.

Don’t miss: Take a break from the slopes and head to Park City’s Historic Main Street, about nine miles away from the hotel, for boutiques, galleries, and cozy bars and restaurants, all strung with holiday lights.

Good to know: With immediate access to the gondola, a ski valet, and heated boot storage, this hotel makes hitting the slopes easy. Pets up to 70 pounds are welcome too (a non-refundable fee applies).

If you want a girls’ trip you’ll be talking about until next year…

Lobby of the Las Vegas Hilton at Resorts World

Las Vegas Hilton at Resorts World

📍 Las Vegas, NV

The lowdown: This 3,500-room resort sits on the north end of the Strip and houses three hotel brands under one roof: Hilton, Conrad, and Crockfords. Between the 50-plus restaurants and bars, the spa with its own Fountain of Youth (!!), and the infinity pool overlooking the Strip, it has everything a girls’ trip needs. Stay a week, and you won’t repeat a meal (or an outfit).

What to eat and drink: Start with a glam dinner at Kusa Nori (modern Japanese) or Stubborn Seed (Michelin-recognized, from Top Chef winner Jeremy Ford). For brunch, FUHU does a Saturday brunch with Asian-inspired dishes, and you can add a Pilates class if you’re feeling virtuous. Save room for dessert at Lady M (home of the famous Mille Crêpes cake) and Junior’s cheesecake.

Don’t miss: Miss Loretta’s, the new rhinestone-cowgirl saloon opening November 15. Expect disco cowboy hats, country and house music on the same stage, and cocktails with names like Emotional Support Cowboy and Pearls Before Yeehaw. Some arrive with a crown of cotton candy or a smoke-filled bubble—Instagram catnip!

Good to know: Resorts World Theatre has concerts lined up for December, and if you’re heading in early December, Rodeo World takes over the resort for the National Finals Rodeo (December 3 to 12), with live country music and watch parties.

If you want a trip the whole family will love…

An aerial view of Hilton Orlando

Hilton Orlando

📍 Orlando, FL

The lowdown: This giant resort has more than 1,400 rooms, a zero-entry pool with a waterslide, a splash pad, and an 892-foot lazy river, so the kids may never want to leave. It’s a mile from Universal’s Epic Universe and minutes from International Drive. It’s also a partner hotel of both Universal Orlando Resort and SeaWorld, which comes with perks.

What to eat and drink: Family-friendly options include FastBreak, the sports bar with an outdoor biergarten, and TodoVos for tacos and margaritas. For a nicer night, book Trabucco, the Italian restaurant with handmade pasta and a patio overlooking the pool.

Don’t miss: Grown-ups can slip away to the adults-only pool (18+), which has whirlpools and cabanas, or enjoy a day at the eforea Spa (2025 Tripadvisor Travelers’ Choice Award winner). There’s also a Topgolf Swing Suite at FastBreak, which is fun for golfers and non-golfers alike.

Good to know: There’s complimentary transportation to the theme parks, which is the real magic. The hotel offers a shuttle to all four Universal parks (including Epic Universe), plus daily scheduled transportation to Magic Kingdom and EPCOT. Disney transportation is included in the resort charge, but make sure to book a reservation in advance.

If you want to wine and dine your way through the city…

The Starling Atlanta Midtown, Curio Collection by Hilton

The Starling Atlanta Midtown, Curio Collection by Hilton

📍 Atlanta

The lowdown: This stylish hotel is right in the heart of Midtown, next to Colony Square with its plethora of restaurants and shops. It’s a five-minute walk from the MARTA station, and Piedmont Park is steps away, too. Foodies, consider this your base camp.

What to eat and drink: Lantana, the hotel’s gold-and-jewel-toned lobby lounge and restaurant, is a must. Order the Baby Hasselback Potatoes and Bang Island mussels, with a Mandarin Ginger Gin Sour on the side. And thank us later.

Don’t miss: The Atlanta Botanical Garden, which is under a mile away. It’s known for holiday lights in the winter, so check what’s on this year. Then catch a show at the Fox Theater, about a mile away, or take a stroll through Piedmont Park to walk off dinner.

Good to know: Art lovers, the High Museum of Art and MODA are both within a mile, which makes them good rainy-day backups.

If you want a long weekend of sunshine without a long flight…

Golf course and ocean at the Hilton La Jolla Torrey Pines

Hilton La Jolla Torrey Pines

📍 San Diego, CA

The lowdown: This coastal retreat sits on the 18th hole of the Torrey Pines Golf Course (yes, the one that hosted the U.S. Open), with picturesque views of the Pacific Ocean. Even if you’re not the biggest golf fan, the hotel boasts a pool, cabanas, daily garden yoga, and a nature reserve with a trail to the beach, all within a mile or so.

What to eat and drink: Start your morning at Torreyana with the lemon ricotta pancakes or the chicken sausage shakshuka. At sunset, grab a craft cocktail by the fire pits and watch the sky turn pink. It’s the best seat in the house. Catching a game? Torreyana Lounge has 14 TVs (including an 82-inch one, nbd).

Don’t miss: A tee time at Torrey Pines, if you play. The hotel reserves exclusive times for guests, and you can warm up on the driving range and putting green. If golf isn’t your thing, walk to Torrey Pines State Beach via the trailhead at the nature reserve, about a mile away. La Jolla Cove is five miles away, where you can spot seals and sea lions sunning on the beach.

Good to know: Golf is booked separately from your room, and tee times sell out fast, so call early. Guests also get a 15% discount at the course’s pro shop. No clubs? You can rent them. The hotel also has pickleball and tennis courts, basketball courts, and bike rentals.

If you want to escape the cold without needing a passport…

Signia by Hilton Diplomat Beach Resort

Signia by Hilton Diplomat Beach Resort

📍 Hollywood, FL

The lowdown: This recently renovated beachfront resort sits between Miami and Fort Lauderdale, with two oceanfront pools, a 15,000-square-foot spa, and an adults-only beach club. You can also kayak, paddleboard, or take a bike ride along the Hollywood Broadwalk.

What to eat and drink: Order guacamole, ceviche, and a cocktail at Playa Beach Bar & Grill, right by the ocean, then watch the sun set at Solara, where the drinks are flowing until midnight. For a dressy dinner, stop by Diplomat Prime, a modern steakhouse with a raw bar.

Don’t miss: The Verandah Social Club, an adults-only hideaway with shaded cabanas, daybeds, and a more private stretch of beach (pictured). You can even book a spa treatment from your cabana, like the Cooling Cryo Wand Facial. And yes, there’s even poolside caviar!

Good to know: This resort is a short drive from Fort Lauderdale-Hollywood International Airport, so you can go from the plane to the pool fast. Book a cabana early, since spots go quickly!

There’s a Hilton for whatever kind of break you need this holiday season. Guests who book directly through Hilton can earn Hilton Honors Points on eligible stays, access member-exclusive pricing, use Points & Money redemptions, and enjoy the benefits associated with their Hilton Honors status. Plan your next getaway today.