Windermere Chalets

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Check dates for Windermere hotels

Chalets in Windermere

Beautiful Resort like Chalet - North Of Orlando In Longwood, Florida

With a stay at this chalet, you'll be centrally located in Longwood, within a 10-minute drive of Greenwood Lakes Park and Spring Hammock Preserve.

Outdoor Space

Free WiFi

The Best Vacation you'll ever have Close to all resorts, gated w/ Pool/Jacuzzi😎

With a stay at this chalet in Four Corners, you'll be within a 15-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club.

Pool

Hot Tub

Watch the Sunrise on Lake Louisa

$131

per night

May 13 - May 14

Located in Clermont (Vacation Village), this chalet is within a 5-minute drive of Lake Louisa State Park and Legends Golf & Country Club.

Air conditioning

Washer

Hidden Gem Jiminy Cricket

4715 Kings Castle Cir, Kissimmee, FL

When you stay at this chalet in Kissimmee, you'll be near the airport, within a 10-minute drive of Old Town and Orlando Vineland Premium Outlets.

Pool

Parking included

Don't see what you're looking for?

See all available properties in Windermere

View all properties

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.