1. WASHINGTON, D.C.
Through year's end, the boutique Hotel Monticello of Georgetown (800/388-2410) has a special Friday- and Saturday-night rate of $250. This gets you a two-bedroom, 11/2-bath suite that can sleep up to six, with a full kitchen. Guests who book round-trip Amtrak travel to Washington through the hotel can also get a 15 percent discount on train tickets.
2. BRITISH VIRGIN ISLANDS
Through November 16, save up to 25 percent with the Admiral's Family Package at the Bitter End Yacht Club (800/872-2392; www.beyc.com) on Virgin Gorda. The five-night plan now costs $3,375 for a family of four and includes a pair of adjoining beachfront villas or suites, all meals, water sports, children's programs, airport transfers, daily excursions, and a sailing course.
You've got until December 14 to snap up a Kids Fly and Play Free package to Disneyland from Alaska Airlines Vacations (800/468-2248; www.alaskaair.com). Prices include round-trip airfare to Los Angeles from most cities served by Alaska Airlines (and its partner Horizon Air), a minimum of three nights in a hotel near Disneyland, a four-day Disneyland Resort Park Hopper Pass, and airport transfers. Sample starting rates for one adult and one child: $475 from Portland, Oreg., or Seattle; $530 from Spokane.
For the same francs you'd spend on a good hotel room, you can rent a furnished flat. The Chicago office of Paris Sejour Reservation (312/587-7707; www.psryourhomeinparis.com) has two-bedroom apartments ranging from $140 to $280 a night, with a required stay of at least five nights. One-bedroom units go for $100 to $200; three-bedrooms from $300 a night. There's also a one-time service fee based on the number of bedrooms and people; a one-bedroom for four people is $148.
The Woodstock Inn & Resort (800/448-7900; www.woodstockinn.com) has scheduled five Family Ski Weeks in January and early February. Priced at $353 per night, the three-night packages provide lodging for two adults and up to four children (in a connecting room), plus ski tickets for Suicide Six or the inn's cross-country center, equipment rentals, one group lesson per person (except for kids five and under), breakfast, transportation from the inn to the slopes, and a ride in a horse-drawn sleigh.
Hyatt's Sunshine on Sale package at the Hyatt Regency Aruba Resort & Casino (800/554-9288; www.hyatt.com) starts at $220 a night, double, through December 18. Children can share their parents' room at no extra cost, or you can book a second room for the kids at 50 percent off—either way, you'll get the fifth night free for each room when you reserve a four-night stay. The rate also provides one free day of supervised Camp Hyatt activities (usually $46 a day per child) for two children.
On October 26, lower rates kick in at Eagle Ridge Inn & Resort in Galena, Ill. (800/892-2269; www.eagleridge.com), about two hours west of Chicago. The price of an Eagle Ridge Getaway package—available every night except Thanksgiving—drops to $259 weekdays/$309 weekends for two nights at the inn (originally $389/$429); for a one-bedroom villa, it falls to $279/$329 (from $419/$479). The package includes a $25 resort credit, 25 percent discount on Saturday youth programs, and reduced rates on spa services plus horseback rides and lessons.
8. PUERTO RICO
The Condado Plaza Hotel & Casino in San Juan (800/468-8588; www.condadoplaza.com) has a Four-for-Free offer for families, available through November 22. With prices starting at $170, double, per night (kids share a room with parents at no charge), it includes a room upgrade, use of the hotel's fitness center, a daily program of supervised children's activities with lunch, and a free fifth night with a four-night stay.
9. SOUTH CAROLINA
Villa rental rates at Kiawah Island Resort (800/576-1570; www.kiawahresort.com), the golf and tennis mecca on a barrier island off the South Carolina coast, drop to their lowest levels in the fall. One-bedroom units start at $109 a night; two-bedroom villas at $139. A two-bedroom ocean-view villa goes for $229 nightly or $1,239 per week (summer prices are $379/$2,729), plus tax and service charge. Rates include an hour of tennis a day.
10. AROUND THE U.S.A.
If your parents are planning to visit the grandkids on an upcoming holiday, check out Candlewood Suites (888/226-3539; www.candlewoodsuites.com), which has locations in Boston, San Francisco, Dallas, Minneapolis, and 93 other cities. Grandparents stay free on Thanksgiving, Christmas, or New Year's Day—or any night, if it's their first time with the chain—when they book a second, paid night. To get this deal, simply flash a photo of a grandchild at check-in.