Whether you’re chasing the sun or embracing festive charm, winter is the perfect time of year to escape. We turned to Olivia Kushner of Arbiter Travel to hear her top resort picks for the 2025 holiday and early 2026 winter season.
From tropical overwater bungalows to cozy coastal escapes, Olivia shares her insider perspective on these sought-after properties. We’ve paired each destination with curated Helen Jon edits that will travel as stylishly as you do.
Enjoy browsing, and happy travels this season!
Four Seasons Resort, Bora Bora
Bora Bora is the perfect destination for an all-out, tropical holiday getaway, and it doesn't get better than the Four Seasons! The iconic overwater bungalows are amazing for couples, while the larger villas with private pools on land are ideal for families. Although often thought of as a honeymoon spot, the property has a wonderful kids club. This resort would make for a great family holiday or special New Year’s getaway!
Montage Palmetto Bluff, South Carolina
For those staying stateside, Montage Palmetto Bluff offers some of the absolute best of the Lowcountry. It truly feels like you're staying at an extended family member's estate. Holiday oyster roast and daily evening s'mores are just some things to love about this property during the holiday season! It has fantastic residence options for multi-gen families — I also love their cottages, and the rooms at the Inn are wonderful as well. Be sure to dine at their on-property restaurant, River House, and if time allows, extend your trip with a visit to nearby Savannah.
Rosewood Kona Village & Mauna Lani, Hawaii
Hawaii is a classic winter escape — and the holidays here are especially magical! Think Santa arriving on the beach, gingerbread house decorating, and letters to Santa. Rosewood Kona Village is an incredible resort on the Big Island. The individual houses are beautiful and real standouts, great for couples or a multi-gen family. Mauna Lani is another favorite on the Big Island that I think is particularly great for families — their food and beverage is some of the best on the island. Don’t miss the unforgettable sunrise canoe paddle!
Four Seasons Resort, Punta Mita
This beachfront paradise is the perfect family beach resort — it would make for an amazing holiday! Lazy river, plenty of pools, and gorgeous beaches (some of the most beautiful I've seen in Mexico). The food and beverage at the Four Seasons is top-notch, and there's something for everyone. They have an adult pool, teen club, and kids club (and even a fun new program called “Babies for All Seasons”), so the whole family will be entertained!
Ojai Valley Inn, California
Ojai Valley Inn is a California gem. The town of Ojai and the Inn itself go all-out for holidays (I was there for Fourth of July this year) — think storytelling with Santa's elves, cookie decorating, and grand Christmas and Hanukkah dinners. If you live nearby, it’s the perfect staycation. It’s extra perfect for the holidays because they’re dog-friendly, so you won’t have to leave your fur babies behind.
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If you’d like to learn more about any of these properties, Olivia would love to help you plan the perfect winter vacation for you and your family. Wherever your travels take you this season, treat yourself to Helen Jon resortwear — luxe pieces that will effortlessly take you from poolside mornings to festive evenings.