An aerial view of a residential area with numerous houses, roads, and several lakes.

Windsor Hills Vacations from $232

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Your Windsor Hills Vacation

Take all the hassle out of planning your next escape with a Windsor Hills vacation package. Take in the sights and sounds of this enticing neighborhood and experience all it has to offer. Eager to sightsee during your trip to Windsor Hills? Be sure to check out nearby attractions like Mystic Dunes Golf Club, Orange Lake Golf and Jack Nicklaus Course. Stop dreaming and start doing. When it's time to book your dream vacation to Windsor Hills, Expedia will help you get there.

The Latest Windsor Hills Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A modern interior with a white spiral staircase, a large Christmas tree, and a dining area with white furniture.
    Jan 10 - Jan 16

    Palazzo Lakeside Hotel + Flight

    Kissimmee
    6 nights
    3.0 star property
    8.4/10 - Very good (5,379 reviews)
    Roundtrip • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    $395
    $232
    per traveler
    found 1 day ago
    Palazzo Lakeside Hotel
  • A resort with multiple buildings, a central pool area, a beach, and a dock with a boat.
    Jan 10 - Jan 16

    Margaritaville Cottages Orlando by Vstays with H2O Waterpark + Flight

    Kissimmee
    6 nights
    4.0 star property
    9.2/10 - Wonderful (1,000 reviews)
    Roundtrip • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    $1,799
    $781
    per traveler
    found 1 day ago
    Margaritaville Cottages Orlando by Vstays with H2O Waterpark
  • A modern hotel lobby with a reception desk, a round coffee table, a sofa, and a large window with curtains.
    Jan 10 - Jan 16

    Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort + Flight

    Kissimmee
    6 nights
    2.0 star property
    9.0/10 - Wonderful (4,096 reviews)
    "Nice spot. To enjoy comfort peace and quiet. Coffee each morning was a bonus"
    Reviewed November 7, 2026
    Roundtrip • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    $830
    $365
    per traveler
    found 1 day ago
    Seasons Kissimmee - Orlando - Lake Buena Vista South, Florida Resort
  • A stone wall, a brown sofa with orange and yellow cushions, a glass table with a fire feature, and a wooden door with decorative glass panels.
    Jan 10 - Jan 16

    The Delaney Hotel + Flight

    South Orange
    6 nights
    3.5 star property
    9.6/10 - Exceptional (1,244 reviews)
    "Great Hotel. Well Located and the staff is very friendly!"
    Reviewed November 6, 2026
    Roundtrip • Boston (BOS) - Orlando (MCO)
    BOS - MCO • Nonstop MCO - BOS • Nonstop
    $1,179
    $580
    per traveler
    found 1 day ago
    The Delaney Hotel
  • A deck with lounge chairs and tables overlooking a beach with palm trees and ocean waves.
    Jan 22 - Jan 26

    Westgate Cocoa Beach Resort + Flight

    Cocoa Beach
    4 nights
    4.0 star property
    8.6/10 - Excellent (577 reviews)
    "Great place!"
    Reviewed November 2, 2026
    Roundtrip • New York (NYC) - Orlando (MCO)
    LGA - MCO • Nonstop MCO - LGA • Nonstop
    $1,090
    $548
    per traveler
    found 1 day ago
    Westgate Cocoa Beach Resort

Where to stay in Windsor Hills

Find the best Windsor Hills areas and neighborhoods for the activities you enjoy most. Learn more about Windsor Hills
Learn more about Windsor Hills
The entrance to the Hollywood Studios area with a large sign and distinctive architecture.
Photo by Gary Burke
Open Photo by Gary Burke

Bay Lake

Home to all four Walt Disney World Resort theme parks and one water park, this city offers endless entertainment, including Disney's Fort Wilderness Resort & Campground and Magnolia and Palm Golf Courses.

A large Ferris wheel with blue lights, surrounded by a cityscape with illuminated buildings and a tall green tower.

International Drive District

Adventure activities, iconic attractions, shopping and world-class dining destinations make this famous street one of Orlando’s most popular tourist attractions.

A roller coaster at Universal Orlando Resort, featuring a tall palm tree and a clear blue sky.
Photo by Peter Sutton
Open Photo by Peter Sutton

Florida Center

While visiting Florida Center, you might make a stop by sights like Universal Orlando Resort and Universal Studios Florida.

A large Ferris wheel with blue lighting, surrounded by a parking lot and buildings.

Champions Gate

Abundant dining options and pristine golf courses are well-reviewed features of Champions Gate. Make a stop by top sights like ChampionsGate Golf Club while you're exploring the area.

A golf course with bunkers, water hazards, and a large lake.

Reunion

The waterparks and pristine golf courses are top of the list for many visitors to Reunion. A stop by Reunion Resort Golf Course or Jack Nicklaus Course might round out your trip.

Windsor Hills Hotel Deals

A resort with multiple swimming pools, palm trees, and lounge areas.

Mickey s Hideaway Windsor Hills Resort

Mickey s Hideaway Windsor Hills Resort
2.5 star property
Windsor Hills
$343 nightly
The price is $389
Nov 29 - Nov 30
Total with taxes and fees
Mickey s Hideaway Windsor Hills Resort
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.
See all properties in Windsor Hills
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.