The cheapest weeks to visit Disney World this winter are usually the ones that avoid holidays, school breaks and big race or festival weekends. Prices, dates and crowds change every year, so use the patterns below as a starting point and check current rates before you book. Staying at a Windsor Hills vacation rental, about 5 to 10 minutes from Disney property, can also help your budget go further.
What makes a week cheap or expensive
Demand drives price. The most expensive stretches tend to be Christmas week, New Year's, and holiday weekends when schools are out. The cheaper weeks sit in between. See our guide to the best time of year to visit with kids for the big picture.
Weeks that are often cheaper
- Early December, once Thanksgiving crowds clear and before school breaks begin.
- Mid-to-late January, after the New Year's rush and outside race weekends.
- Many weeks in late January and early February that don't line up with a school holiday weekend.
- Midweek stays, since weekends often cost more for rentals.
Watch for events that pull in crowds, like the runDisney weekend in January. Our Marathon Weekend guide explains how that week works, and our January guide covers what to expect around it.
Weeks to watch out for
Christmas through New Year's is typically the busiest and priciest stretch, and holiday weekends fill up quickly. If your dates are fixed, book earlier. Our booking timeline shows how far ahead to reserve a vacation home.
Save more once you've picked your week
- Cook some meals in your rental's full kitchen. Our dining plan vs. cooking comparison breaks down the costs.
- Know what you can bring into the parks with our food rules guide.
- Split a larger rental with family. A condo, townhouse or private-pool home gives you more space than a single hotel room.
- Ask the owner about pool heat. Most Windsor Hills owners now include private pool heat at no charge, but confirm before booking.
Compare the total cost, not just the week
A cheap week can still add up if you overlook fees. Ask each owner what the nightly rate includes, and compare the full total with cleaning fees and taxes added. Our rental cost breakdown shows what to look for. Also weigh flexibility: if you can shift your trip by a few days, the same home may cost noticeably less. Booking a slightly longer stay at an off-peak time can lower the per-night cost compared with a short stay in a busy week.
Use the resort on your cheapest days
A low-cost day can be a pool day. The Windsor Hills lagoon pool is heated, and the Sir Windsor AquaVenture water park, splash areas, putting green, games room and courts are all on site for guests. There is no resort shuttle to Disney, so plan on driving or a rideshare; the drive is usually under 15 minutes.
Find your week and book direct
Windsor Hills is a gated resort, and booking direct with owners lets you compare rates for the weeks you're considering. Check Disney's website for current ticket prices and dates, then browse Windsor Hills rentals.
