Going on a vacation during the holidays is a special experience; the world is adorned in festive lights and decorations, the air is filled with a palpable sense of joy and goodwill, and everything feels slightly more magical.
Whether you’d like to embark on a snowy winter getaway or bask in the sun on a tropical beach, the holidays provide a unique opportunity to escape the routine of daily life and create lasting memories with loved ones—from cozying up by the fire with hot cocoa to exploring new cultures and traditions.
Inspirato homes offer the perfect place to come together, offering expansive, gorgeous spaces with room for everyone to gather—and spread out when needed. Here are a few of our favorite homes where Inspirato members can spend their winter break, holiday weeks, or New Year’s celebrations.
Casa Gardenias — Los Cabos, Mexico
This penthouse unit within the Auberge Private Residences at Esperanza sleeps up to 10 people across four bedrooms. Located just steps from a gorgeous resort pool, Casa Gardenias features a glimpse of the ocean and a spacious outdoor patio. Its open layout with vaulted ceilings offers an ideal space for family and friends to gather for a warm-weather holiday getaway. A stay here includes the use of a golf cart to take you to resort amenities like the spa, restaurants, fitness center, and more.
Andesite — Big Sky, Montana
Get cozy this holiday season around the fireplace at Andesite, a modern mountain home in the Spanish Peaks neighborhood of Big Sky, Montana. Take in surrounding views of the old-growth pines and rugged mountain peaks from floor-to-ceiling windows in the open living area. Located within walking distance of the Highlands ski lift, you can easily enjoy legendary skiing at Big Sky and come home to relax in the outdoor hot tub under the stars.
Hepburn — New York City, New York
New York City is one of the best places to experience holiday magic—from extravagant decorations adorning the streets to charming winter markets. Stay in the heart of it all at Hepburn, a four-bedroom brownstone located on one of the most exceptional blocks of the Upper East Side, just six blocks from Central Park. With multiple fireplaces, several living areas, a wine cellar with wet bar, and a library, there are so many places to come together and enjoy the holidays in this chic space.
Water Lily — Hilton Head Island, South Carolina
This classic Lowcountry home has tons of outdoor living space, including a heated pool and screened-in porch with a fireplace perfect for those cooler temps during holiday season. And with Water Lily’s expansive gourmet kitchen, two indoor living areas, and five bedrooms, there’s plenty of space for up to 10 guests to gather together inside, too. Spend your days taking long winter walks on the beach close by, or head to the golf course just steps away.
Sunset Cottage — Rosemary Beach, Florida
Enjoy the holidays at the beach with a stay at Sunset Cottage, a four-bedroom home located within WaterColor Resort that gives you full access to resort pools, restaurants, a spa, and more. Plus, the home has its own private pool and hot tub. Enjoy the warm weather from a spacious screened-in upper deck and lower-level porch or enjoy an evening playing games or watching movies in the oversized family room. And if you’re feeling motivated, Sunset Cottage also has a Peloton bike for an in-home workout.
Cherrybrook — Breckenridge, Colorado
Embrace winter and the holiday season at Cherrybrook, a four-bedroom home with room for 12 guests. This mountain home is nestled just five minutes from charming Breckenridge that comes alive during the holidays with twinkling lights and festive decorations. Spend the day skiing or snowboarding, snow tubing, or snowshoeing, then come home to soak in your own private hot tub. Breckenridge is also a great place to take a festive sleigh ride through the snowy forest—what better way to experience holiday magic.
