Windsor Hills Hotels, Orlando

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Filter by

Guest rating
Guest rating
Star rating

1836 Cheap Hotels in Windsor Hills - Specials, Reviews, & Last Minute Deals

Magical Adv 5 Star Villa Movie Room Arcade Pool and More

2.0 star property
Windsor Hills
Magical Adv 5 Star Villa Movie Room Arcade Pool and More

The Grove Resort & Water Park Orlando

4.0 star property
6.9 km from Windsor Hills
8.0 out of 10, Very good, (8744)
"Great stay"
United States
Breanna
The price is NZ$365
includes taxes & fees
18 Nov - 19 Nov
The Grove Resort & Water Park Orlando

Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

4.0 star property
10.4 km from Windsor Hills
9.2 out of 10, Wonderful, (3930)
"Nice place to stay for family. "
United States
Niketan Chhaganbhai
The price is NZ$196
includes taxes & fees
7 Dec - 8 Dec
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando

Westgate Lakes Resort & Spa Universal Studios Area

4.0 star property
16.9 km from Windsor Hills
8.2 out of 10, Very good, (5498)
"Great staff and resort"
United States
Parker
The price is NZ$245
includes taxes & fees
30 Nov - 1 Dec
Westgate Lakes Resort & Spa Universal Studios Area

Kompose Boutique Resort at Theme Parks

3.0 star property
1.8 km from Windsor Hills
9.4 out of 10, Exceptional, (1787)
"Everything about the hotel was excellent, from location to amenities. "
United States
Sheilla Maria
The price is NZ$188
includes taxes & fees
18 Nov - 19 Nov
Kompose Boutique Resort at Theme Parks

Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

4.0 star property
13.8 km from Windsor Hills
9.2 out of 10, Wonderful, (2604)
"Stayed here before always enjoyed it "
United States
Margaret
The price is NZ$190
includes taxes & fees
8 Dec - 9 Dec
Sheraton Vistana Villages Resort Villas, I-Drive/Orlando

Rosen Inn International

3.0 star property
18.9 km from Windsor Hills
8.4 out of 10, Very good, (5880)
"Yes was really clean staff very nice people "
United States
Francis
The price is NZ$154
includes taxes & fees
18 Nov - 19 Nov
Rosen Inn International

Rosen Inn Lake Buena Vista

3.5 star property
12.1 km from Windsor Hills
8.6 out of 10, Excellent, (5574)
"Amazing stay "
United States
Elsy
The price is NZ$133
includes taxes & fees
24 Nov - 25 Nov
Rosen Inn Lake Buena Vista

DoubleTree by Hilton at the Entrance to Universal Orlando

4.0 star property
22.1 km from Windsor Hills
8.4 out of 10, Very good, (6844)
"Great stay "
United States
Anthony
The price is NZ$193
includes taxes & fees
24 Nov - 25 Nov
DoubleTree by Hilton at the Entrance to Universal Orlando

Hyatt Regency Grand Cypress

4.0 star property
11.3 km from Windsor Hills
9.2 out of 10, Wonderful, (2288)
"Rooms were a nice size and clean, we enjoyed the property grounds and overall atmosphere of the hotel."
United States
Casey
The price is NZ$445
includes taxes & fees
29 Nov - 30 Nov
Hyatt Regency Grand Cypress

Home2 Suites by Hilton Orlando at Flamingo Crossings

3.0 star property
7.1 km from Windsor Hills
9.2 out of 10, Wonderful, (4938)
"Really nice place to stay and the breakfast was really great to have each morning. "
United States
Amanda Kay
The price is NZ$204
includes taxes & fees
30 Nov - 1 Dec
Home2 Suites by Hilton Orlando at Flamingo Crossings

Seasons Florida Resort

2.0 star property
12.4 km from Windsor Hills
8.8 out of 10, Excellent, (3242)
"Great place!"
United States
Andrea
The price is NZ$112
includes taxes & fees
18 Nov - 19 Nov
Seasons Florida Resort

Hotel Monreale Express and Studios IDrive District

3.0 star property
18.4 km from Windsor Hills
7.4 out of 10, Good, (3038)
"Definitely enjoyed my stay, great location and friendly atmosphere "
United States
Regina
The price is NZ$138
includes taxes & fees
18 Nov - 19 Nov
Hotel Monreale Express and Studios IDrive District

Holiday Inn Club Vacations at Orange Lake Resort by IHG

4.0 star property
Orange Lake, 4.6 km from Windsor Hills
8.8 out of 10, Excellent, (2492)
"My fave place to stay when in Orlando."
United States
Jodi
The price is NZ$311
includes taxes & fees
25 Nov - 26 Nov
Holiday Inn Club Vacations at Orange Lake Resort by IHG

Clarion Inn & Suites Across From Universal Orlando Resort

3.0 star property
22.2 km from Windsor Hills
8.0 out of 10, Very good, (1919)
"Nice place to stay loved the room and pool area staff was great "
United States
Andrea
The price is NZ$157
includes taxes & fees
23 Nov - 24 Nov
Clarion Inn & Suites Across From Universal Orlando Resort

Holiday Inn Express & Suites Clermont Se West Orlando by IHG

2.5 star property
6.8 km from Windsor Hills
8.4 out of 10, Very good, (1024)
"Great room great breakfast"
United States
Kelly
The price is NZ$197
includes taxes & fees
16 Dec - 17 Dec
Holiday Inn Express & Suites Clermont Se West Orlando by IHG

Summer Bay Orlando by Exploria Resorts

3.5 star property
6.8 km from Windsor Hills
8.8 out of 10, Excellent, (2070)
"The staff are very friendly and the resort is gorgeous! "
United States
Katherina
The price is NZ$261
includes taxes & fees
1 Dec - 2 Dec
Summer Bay Orlando by Exploria Resorts

Vacation Village Orlando, Celebration

3.0 star property
6.6 km from Windsor Hills
8.6 out of 10, Excellent, (3040)
"Great place to stay"
United States
Jose
The price is NZ$226
includes taxes & fees
1 Dec - 2 Dec
Vacation Village Orlando, Celebration

Holiday Inn Resort Orlando Suites - Waterpark by IHG

3.5 star property
9.2 km from Windsor Hills
7.0 out of 10, Good, (4403)
"Nice with good dining options "
United States
Maria G.
The price is NZ$251
includes taxes & fees
18 Nov - 19 Nov
Holiday Inn Resort Orlando Suites - Waterpark by IHG

Avanti International Resort

4.0 star property
18 km from Windsor Hills
7.8 out of 10, Good, (4218)
"Great places "
Canada
Felipe
The price is NZ$185
includes taxes & fees
14 Dec - 15 Dec
Avanti International 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.

Hotels in Windsor Hills with free breakfast

Hotels in Windsor Hills with a pool

Top guest rated hotels in Windsor Hills

Our guide on where to stay in Windsor Hills

Find the best Windsor Hills areas for the activities you enjoy most.

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.

Bay Lake

Exciting theme parks plentiful wildlife and top sights from Epcot® to Walt Disney World® Resort – discover Bay Lake, a destination also famous for its entertainment.

Downtown Orlando

One of the most popular neighborhoods in Florida, this bustling area is full of art galleries, shops, bars and restaurants.

Florida Center

If you're spending some time in Florida Center, Universal Orlando Resort and Universal Studios Florida are top sights worth seeing.

Champions Gate

Ample dining options and top 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.

Top Windsor Hills Hotel Reviews

Find out more about Windsor Hills

Top reasons to visit Windsor Hills

  • Family-Friendly Resort: Windsor Hills is a vibrant community ideal for families, offering a mix of outdoor fun and relaxation.
  • Thrilling Theme Parks: Enjoy close proximity to renowned theme parks for unforgettable adventures.
  • Windsor Hills Water Park: Experience exciting water slides and pools, perfect for a day of splashes.
  • Variety of Accommodations: Choose from luxurious resorts to charming vacation rentals, catering to all needs.
  • Beautiful Outdoor Activities: Explore picturesque lakes and golf courses, ensuring a delightful experience for everyone.

Find great hotels near Windsor Hills

Windsor Hills offers a fantastic selection of accommodation options, perfect for families, couples, and pet owners seeking a memorable getaway. From luxurious resorts to charming vacation rentals, including condos and homes, you'll find something that suits your needs. Located in the heart of Four Corners, Florida, this destination provides easy access to attractions while ensuring a relaxing and enjoyable stay.

  • Hilton Vacation Club Aqua Sol Orlando West: Emphasising a family-friendly atmosphere, Hilton Vacation Club Aqua Sol Orlando West is a delightful 3.5-star hotel located a mere 6.4km from Windsor Hills. This property offers a vibrant array of amenities aimed at providing a fun-filled experience for families and LGBTQIA travellers alike. Children can enjoy the free WaterPark, an exciting Arcade Game Room, and a shared playground. With onsite mini-golf, there's plenty to keep the kids entertained while parents unwind in a welcoming environment.
  • Hilton Vacation Club Mystic Dunes Orlando: Situated just 805m from Windsor Hills, Hilton Vacation Club Mystic Dunes Orlando is a versatile 3.5-star hotel that caters to both family and business travellers. The hotel boasts excellent business amenities, including a 24-hour Business Centre and accessible meeting rooms, making it an ideal choice for those merging work and play. Children are also well catered for with onsite mini-golf, foosball tables, and ping pong, ensuring a balanced experience of recreation for the whole family.
  • Walt Disney World Dolphin: A standout among the accommodations near Windsor Hills, the 4-star Walt Disney World Dolphin is perfect for those seeking a beachside retreat while enjoying family-friendly amenities. Located 6.4km away, this property provides direct access to the beach and a welcoming atmosphere for LGBTQIA travellers. Families will appreciate the supervised childcare services, arcade game room, and shared playground, creating a stress-free environment for both parents and children to enjoy their holiday.

Where to stay near Windsor Hills

Windsor Hills, nestled in Kissimmee, Florida, is an ideal family-friendly resort community perfect for a fun-filled holiday. With its vibrant atmosphere and friendly locals, visitors can enjoy a variety of outdoor activities and recreational opportunities. Explore nearby attractions or relax in comfortable accommodation options that cater to families. Whether it's a thrilling theme park adventure or a leisurely day by the pool, Windsor Hills offers an unforgettable vacation experience for everyone.

  • Orlando: A vibrant metropolis and the heart of Florida's entertainment scene, Orlando is renowned for its theme parks, shopping districts, and cultural venues. Situated just a stone's throw from Windsor Hills, this bustling city welcomes millions of visitors year-round, with peak travel periods in March, July, and December. Families flock to Orlando for its outdoor experiences and family-friendly attractions, including iconic theme parks and film studios. Don't miss exploring the local arts centres and indulging in some retail therapy at the shopping areas that dot the landscape.
  • Four Corners: Just a short drive from Windsor Hills, Four Corners is a charming village that serves as a gateway to a myriad of recreational activities. With travel peaks occurring between February to March and during July, this area is perfect for families seeking outdoor adventures and entertainment. Enjoy access to beautiful golf courses and luxurious resorts while being in close proximity to major theme parks and stadiums. Four Corners beautifully balances relaxation and excitement, making it an ideal spot for a family getaway.
  • Crestwynd Bay: Located a mere 483m from Windsor Hills, Crestwynd Bay is a delightful neighbourhood that offers a warm community atmosphere and a plethora of family-friendly activities. With visitor numbers peaking in March, July, and December, it’s an excellent choice for those looking to immerse themselves in Florida's outdoor lifestyle. Here, you can enjoy fantastic resorts, shopping areas, and golf facilities, all while being close to popular landmarks such as theme parks and stadiums. Crestwynd Bay combines the best of leisure and adventure for an unforgettable holiday experience.

Things to do near Windsor Hills

Windsor Hills is perfect for families seeking an entertaining outdoor vacation. Nearby, you can enjoy activities like the Mighty Jungle Golf and visit thrilling theme parks. Additionally, the area boasts a delightful resort atmosphere and various shopping spots, along with fantastic golf options. It's an ideal destination for those looking to create lasting memories with loved ones in sunny Florida.

Shopping

Disney Springs™, located 9.7km from Windsor Hills, offers a vibrant shopping experience with a mix of family-friendly options. Old Town, 8.0km away, combines entertainment and shopping in a lively atmosphere. For unique finds, visit the 192 Flea Market, 14.5km away, brimming with local treasures.

Recreation

At ESPN Wide World of Sports Complex, immerse yourself in vibrant sports energy just 4.8km away. Enjoy a round at Mystic Dunes Golf Club, a scenic 1.1km away, perfect for outdoor enthusiasts. For wellness and relaxation, Northeast Regional Park, located 6.4km away, offers a tranquil escape.

Adventure

Experience the thrills at Disney's Typhoon Lagoon Water Park, located 8.0km from Windsor Hills, where you can enjoy water rides and family fun. For karting enthusiasts, Kissimmee Go-Karts, 12.9km away, offers an adrenaline-pumping experience. Don’t miss the USA Water Ski & Wake Sports Foundation Hall of Fame Museum, 11.3km away, for outdoor sports excitement.

Nightlife

Experience the thrilling medieval battles at Medieval Times, only 12.9km away, while enjoying a night filled with culture and romance. For an adventure-filled evening, visit Wonderworks, located 17.7km away, or catch a captivating film at Regal Pointe Orlando, also 17.7km from Windsor Hills.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Windsor Hills

To save money on your trip to Windsor Hills, consider visiting during the cheaper months of August, September, and November. Booking your hotel about a month in advance typically yields the best rates, and Tuesdays are the least expensive days to stay. Use Expedia to find budget-friendly accommodation, and look out for last-minute deals marked by a green banner. Combine your hotel bookings with flights and activities for additional savings, and explore public transport options to keep travel costs low. Lastly, check for eco-certified hotels for sustainable choices that won't break the bank.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay around Windsor Hills are August to September and November, where the prices are slightly lower. This is in comparison to March to April and December, where prices are slightly higher.
  • The best time to book a hotel: Booking a hotel around Windsor Hills about 1 month out from when you are planning to stay is usually when prices are lowest. If you're a little more spontaneous, you could also peruse Expedia's last minute deals for hotels, look out for the green banner below the price, as this indicates a cheaper deal.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay around Windsor Hills is Tuesday. The most expensive day to stay around Windsor Hills is Saturday.
  • Find cheap hotels on Expedia: Expedia's search tool lets you choose your budget, desired location, and additional preferences. You can arrange the results to display prices from lowest to highest, making it easy to find the most affordable accommodation first. Additionally, you can refine your options by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels available for booking.
  • Consider bundling your trip: You can save some cash by combining your Windsor Hills hotel stay with your flights and activities through an Expedia package deal.

Find the best attractions near Windsor Hills

Windsor Hills is perfect for families seeking outdoor fun and entertainment. Popular attractions include theme parks, picturesque lakes, and golf courses. Don't miss the Windsor Hills Water Park for an exciting day of splashes and slides. Whether you're enjoying thrilling rides or relaxing by the water, there's something for everyone to create lasting memories in this vibrant locale.

  • Walt Disney World® Resort: Experience the magic at Walt Disney World® Resort, a world-renowned theme park located 11.3km from Windsor Hills. With thrilling rides, beloved characters, and enchanting shows, it's a place where families can create unforgettable memories together.
  • Orange County Convention Center: Immerse yourself in culture at the Orange County Convention Center, situated 16.1km away. This vibrant arts centre hosts a variety of events and exhibitions, showcasing local and international talent in a dynamic setting.
  • ChampionsGate Golf Club: Enjoy a family-friendly day at ChampionsGate Golf Club, located 6.4km from Windsor Hills. This golf course accommodation offers stunning greens and friendly staff, making it perfect for both seasoned golfers and newcomers looking to unwind.

Best time to go to Windsor Hills

The best time to visit Windsor Hills is dependant on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are average and weather is mostly sunny with moderate rain. January is its coolest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January60.6°F (15.9°C)Light RainMostly SunnySlightly HighAverage
February64.4°F (18.0°C)Light RainMostly SunnyAverageAverage
March67.6°F (19.8°C)Light RainMostly SunnySlightly HighSlightly High
April72.7°F (22.6°C)Light RainMostly SunnySlightly HighSlightly High
May77.2°F (25.1°C)Light RainMostly SunnyAverageAverage
June81.1°F (27.3°C)Light RainMostly SunnyAverageAverage
July82.4°F (28.0°C)Moderate RainMostly SunnyAverageAverage
August82.6°F (28.1°C)Moderate RainMostly SunnyAverageSlightly Low
September80.4°F (26.9°C)Moderate RainMostly SunnyAverageSlightly Low
October75.2°F (24.0°C)Light RainMostly SunnySlightly LowAverage
November68.5°F (20.3°C)Light RainMostly SunnySlightly LowSlightly Low
December64.4°F (18.0°C)No RainMostly SunnySlightly LowSlightly High

The nearest major airports for your trip to Windsor Hills

Windsor Hills is conveniently accessible via two major airports. Orlando International Airport (MCO) is situated 30.6km away, with top hotels like The Ritz-Carlton Orlando, located 12.9km from the airport, offering amenities such as 24-hour airport shuttles. Another nearby option is Hyatt Regency Orlando, 16.1km from MCO, which also provides shuttle services. Kissimmee Gateway Airport (ISM) is closer at 16.1km, with luxurious hotels such as Waldorf Astoria Orlando, just 11.3km away, offering transfers and shuttles. Additionally, the Conrad Orlando at Evermore is located 16.1km from ISM, ensuring easy access for travellers.

Explore a world of travel with Expedia

Frequently asked questions

What's it like in Windsor Hills?
Travellers will be sure to enjoy their time in Four Corners's Windsor Hills neighbourhood.
Where is the best place to stay in Windsor Hills?
For your stay in Windsor Hills, Villa 7748 - Updated Home w/ Arcade Rm! 3 mi from Disney, Pool Heat, BBQ & PS5 is one of the top choices based on our traveller data. Other good choices for your stay in the neighbourhood include 2 Bedroom, 2 Bath Condo 2 miles from Disney and 10 miles from Universal studios. and Our DisneyDreamVilla - minutes to DisneyWorld!!!.
How many hotels can I expect to find in the Windsor Hills area?
Expedia has 1816 hotels and other accommodation options in Windsor Hills to choose from, making this an ideal home base for exploring the greater Four Corners area.
If I need to cancel my hotel reservation in Windsor Hills, will I receive a refund?
Yes, the majority of room reservations are fully refundable provided that you cancel before the hotel's cancellation deadline, which is usually within 24-48 hours of check in. If you have a reservation that's non-refundable, you might be able to still cancel and be given a refund within 24 hours of booking. Enter dates in and click on "Search", then filter by "fully refundable" to review the best options available in Windsor Hills.
What are the top things to see and do in Windsor Hills?
Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports Complex are some popular places to visit in the area around Windsor Hills. While you're out sightseeing in Four Corners, make sure that you visit other sights such as Mystic Dunes Golf Club or Bonanza Golf & Gifts.