By: Andrea Denali
Picture a real Christmas together. Not a quick hello in a crowded lobby, not a cluster of small apartments where everyone eats in shifts, but one long table, one tree, one address. The kitchen hums. Aunties trade recipes. Kids chase cousins from the game room to the yard. Grandparents settle into a good chair and watch it unfold. That scene is hard to pull off now, which is why more families are booking a single private estate and letting the holiday stretch out the way it used to.
Drip Castle Estate Collection was built for that exact week. The portfolio spans Captiva Island, Florida, Stowe, Vermont, and Taos, New Mexico, and each property is designed for large groups that want privacy, space, and service. We are talking real square footage, not a technical headcount. Sea Oats Luxury Estate on Captiva offers roughly 10,000 square feet with 11 bedrooms, nine of them ensuite. Sea Palms Estate, also on Captiva, tops 9,000 square feet with nine ensuite bedrooms and direct beachfront. Meadowstone Manor in Stowe has 14 guest bedrooms, all ensuite, set on approximately 30 private acres. Gem Hacienda in Taos spans about 8,000 square feet on eight acres, with nine ensuite bedrooms and mountain views.
Greg Barry, who founded Drip Castle with his wife, Michelle, puts the reason families come back in simple terms. “It’s great to be able to get that many people together under one roof and comfortable, to be able to hang out and do activities.” That is the holiday promise here. Everyone under one roof, no one cramped, and plenty to do.
The experience starts before arrival. Drip Castle pairs every booking with a concierge who handles the planning. Groceries are stocked. Private chefs can be scheduled for a full holiday menu or a few special meals. Activities and reservations are lined up so the group can move through the week without constant decision-making. Michelle describes it this way: “When they arrive, they are truly on vacation.” For Christmas, that matters. You want the time together, not a long list of logistics.
The kitchens are a quiet show of force. They are built for real cooking, the kind that takes up counters and draws a crowd. There is room for multiple hands to chop, stir, and taste. The estates are stocked with the serving pieces and practical gear that big family meals actually need. If you prefer to hand off the meal entirely, the concierge team can bring in a private chef for a traditional feast or a modern twist. Either way, the space is there and the holiday unfolds around the stove.
Scenes change by location. In Stowe, Christmas looks like snow on open meadows, a spring-fed pond under frost, and a quick drive to Mount Mansfield for skiing. Meadowstone’s two hot tubs, fireplaces, and pub create warm gathering points after the hill. In Taos, Gem Hacienda pairs high desert light with fireplaces and views of the mountains. Skiers head to Taos Ski Valley while others browse galleries and museums in town. On Captiva, the script flips. Sea Palms is direct beachfront, so the holiday table might sit near open terrace doors as the sun drops into the Gulf. Sea Oats stretches along the bay with a private dock and a quiet path to the sand. Mornings start with beach walks. Afternoons drift into paddleboarding, kayaking, and unhurried time by the pool.
Across the collection, the through-line is comfort at scale. Bedrooms feel considered. White linens keep it clean and crisp. Ensuite bathrooms cut down on the small frictions of a big group. Common areas are large enough for a crowd to gather without feeling stacked on top of each other. For families with young children or older relatives, that mix of space and calm sets the tone. There is room for s’mores by the fire, a puzzle on the table, and a movie night that does not wake the baby.
Families also appreciate that every estate is in the United States. No passports. Fewer travel hurdles. For many, that means grandparents can join more easily and with peace of mind. Drive-to access is part of the draw. Captiva is a straightforward trip for guests coming from Florida cities and retirement communities. Stowe pulls from the Tri-State and New England. Taos attracts the Southwest and anyone who wants mountain air without crossing an ocean.
Activities are there if you want them, and the concierge can scale as needed. Tennis and pickleball. Yoga and in-home massage. Dolphin and sunset tours straight from the Sea Oats dock. Brewery and distillery stops in Vermont. Art and culture itineraries in Taos. The point is not to pack the schedule. It is to make it easy to choose, then return to the same shared living room when the day slows down.
Guest feedback mirrors the intent. One corporate client who uses the collection for team off-sites summed up what also resonates for families. The thoughtful layout, private rooms, and on-property activities create natural chances to connect. It is the same outcome at Christmas. People keep running into each other in the best way. Coffee ends up long. Games get competitive. Stories fill the house.
If you want the holiday to feel like it did years ago, space is the secret. A tree that fits the room. A dining table that fits the family. A kitchen that can handle the menu you actually cook. The rest is simple. A walk on the beach. Fresh snow and cocoa. A few hours where the only plan is being together.
That is what Drip Castle sells without ever saying a word about it. Not a slogan. A week that carries real weight. The kind you remember in March and bring up next summer. The kind you want to repeat.
For families mapping out future holidays now, the advice is basic and useful. Pick the backdrop that matches your crew. If your people want the Gulf in winter and long golden afternoons, book Captiva. If your crew hears sleigh bells and sees ski tracks, choose Stowe. If your group splits between skiers and art lovers, Taos threads the needle. Then let the concierge do the heavy lift and save your energy for what you came for.
The modern holidays ask a lot of us. Travel schedules, school breaks, work calendars. Finding one house that fits everyone sounds impossible until you see how these estates are built. Big rooms. Real kitchens. Private space when you need it. Shared space when you want it. That is the heart of a good Christmas, and it is still possible.
More information and full property details at https://www.dripcastleestatecollection.com/
