The Four Seasons, Punta Mita

Not the most traditional setting for Christmas—but who can resist white sand and whale sightings? This five-star resort north of Puerto Vallarta offers contemporary villas with Mexican accents and striking five-bedroom suites—one totaling 20,455 square feet, with spa and media room. There’s also the resort spa, sports facilities, and a children’s program. Villas start at $5,950 a night.

The Resort at Paws Up, Greenough

This 37,000-acre ranch in Blackfoot Valley will provide Christmas trees (decorated or D.I.Y.), Santas, and traditional holiday meals in their two-, three- and four-bedroom houses, plus activities such as skating and sleigh rides. Don’t feel like cooking for Thanksgiving either? They offer a similar arrangement that week. $6,241 for five nights, for two adults and two children.

Winvian; Morris, Connecticut

This resort is home to 19 whimsical cottages, each designed by a different architect and with a different theme—including a tree house and a helicopter—on 113 acres in New England. Winvian has a 5,000-square-foot spa, snowshoeing, cross-country skiing, and a gourmet restaurant. Antiquing, shopping, and restaurants are nearby. Cottages from $1,450 a night; full property for $35,000.

Villa Mangiacane, San Casciano

This 16th-century villa in Chianti offers Christmas in the Italian manner for 18 guests. It includes a traditional dinner with wine produced on the estate, cooking lessons, and spa treatments. And all of the cultural attractions of Florence are a short drive away. $4,000 a day for up to 18. For other European estates, contact Marina Gratsos of Carpe Diem Travel or try Homes Away.

Canouan Island, Grenadines

Attached to the Raffles resort on this tiny island is are multi-bedroom villas with infinity pools and separate guest cottages. There is a butler and private chef to do Christmas dinner, a tree-lighting ceremony, and a service in the property’s 19th-century church. Villas are $10,000 a night; suites start at $4,450. To make travel easy, you can charter the Raffles jet from Barbados.

Park Hyatt Beaver Creek

This ski-in, ski-out hotel offers easy access to lifts, including one just for children, as well as all the amenities of Beaver Creek village. Rooms and suites in this large hotel can be grouped on one corridor to keep the family together. For nonskiers, there’s also a $12 million spa with a separate water sanctuary. Rates start at $849 a night.

The Greenbrier, White Sulphur Springs

This grand resort has 10 huge lobbies, 721 rooms—including several separate estates with up to seven bedrooms—and 6,500 acres for sleigh riding, cross-country skiing, and carriage rides. There’s a 40,000-square-foot spa built around the hot springs that have drawn guests since the 18th century, and special holiday activities. Rooms start at $445 a night.

The Dorchester

This grande dame goes all out for Christmas, with special meals, Christmas trees, Santa visits, and carol singing. The staff will help you buy presents and book skating time at the ice rink in Hyde Park. If money isn’t a concern, consider the three new rooftop suites decorated by Alexandra Champalimaud, with views overlooking the park. They start at $4,200 a night; the cost for other rooms vary.