Windsor Hills Vacation Packages 2025/2026 from $280

Windsor Hills flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Westgate Towers Resort

Save 100% on your flight

per person

Sep 5 - Sep 10

found 24 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

This hotel features an outdoor pool and a gym. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the hot tub and perks like free self parking.

Westgate Palace Hotel / Universal / I-Drive

International Drive

per person

Sep 3 - Sep 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This resort features an outdoor pool, a gym, and a restaurant. Bring the family and enjoy the children's pool, free theme park shuttle, and kid-friendly dining. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi.

Westgate River Ranch Resort & Rodeo

per person

Aug 14 - Aug 20

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

This smoke-free resort features free water park access, a marina, and 2 restaurants. There's fun for all ages with mini golf and a playground, and barbecue grills are available on site. Relax with a drink at one of the 3 bars/lounges and enjoy perks like free self parking.

CoCo Key Hotel and Water Resort

International Drive

Save 100% on your flight

per person

Aug 11 - Aug 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

Free water park access, 4 restaurants, and 3 outdoor pools are all featured at this traditional hotel. There's fun for all ages with a children's pool and a theme park shuttle, and families will appreciate the onsite laundry facilities. Traveling on business? Take advantage of the 24-hour business center, express check-out, and valet parking.

Westgate Blue Tree Resort in Lake Buena Vista

Save 100% on your flight

per person

Aug 25 - Aug 31

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This hotel features an outdoor pool and a gym. There's fun for all ages with mini golf and a children's pool, and barbecue grills are available on site. Enjoy the hot tub and perks like free self parking.

Top Windsor Hills hotels deals

6/4 Home Pool/Spa Close to Disney, Free Water Park Use, Game RMThemed, WIFI BBQ

Get rates

A water park and a hot tub are featured at this smoke-free vacation home. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the gym and conveniences like a garden and barbecue grills.

Pool

Hot Tub

2Pool Home Water Park Disney 2 m Universal Sea World! By Mystic Dunes golf !

Get rates

This vacation home features an outdoor pool and a gym. Enjoy the hot tub and conveniences like a garden and laundry facilities.

Pool

Hot Tub

Magical 4 Bedroom Villa with Private Pool Minutes from Disney! Free Pool Heat!

Get rates

A water park and an outdoor pool are featured at this smoke-free vacation home. Families will appreciate the arcade/game room and onsite laundry facilities. A gym and a hot tub are also provided.

Pool

Hot Tub

Villa 7748 - Arcade Rm Updated Mar 2025! 3 mi from Disney, Pool Heat, BBQ & PS5

Get rates

A water park and an outdoor pool are featured at this smoke-free vacation home. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. A gym, a hot tub, and barbecue grills are also on offer.

Pool

Hot Tub

Magical Harry Potter Themed Condo

Almaton Loop 2813, Kissimmee, FL

Get rates

An outdoor pool is featured at this apartment, along with free self parking. WiFi in public areas is free. A garden is also provided.

Pool

Kitchen

1Disney 2 miles, Animal Kingdom, south facing pool Home 3/3 Water Park

Get rates

This vacation home features an outdoor pool and a hot tub. A garden and laundry facilities are also provided.

Pool

Hot Tub

Don't see what you're looking for?

See all available properties in Windsor Hills

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.

Popular places to visit

Walt Disney World® Resort

4.5/5(2,427 reviews)

Have a fun-filled day at Walt Disney World® Resort and find out why this is a popular theme park in Lake Buena Vista. Discover the top-notch restaurants and acclaimed theater scene in this walkable area.

Universal Studios Florida

4.5/5(9,273 reviews)

Movie sets and thrill rides combine to create this internationally acclaimed theme park.

Universal Studios Orlando showing street scenes, a city and rides

Universal Orlando Resort

4.5/5(4,155 reviews)

Have a fun-filled day at Universal Orlando Resort and see why people love this theme park in Orlando. Check out the shops and top-notch restaurants in this family-friendly area.

Frequently asked questions

How much are vacation packages to Windsor Hills?

With Travelocity vacation packages, you can live it up in Windsor Hills for a mere $280. Flights, hotels and tours --- we have it all. You'll save loads just for bundling your bookings. With everything taken care of before you go, you can sit back, relax and not worry about a thing.

Where can I get the best vacation package deals for Windsor Hills?

It's difficult to beat Travelocity when it comes to putting together your Windsor Hills package deal. There are as many as 400 airlines and 1,000,000 worldwide properties to select from. Reserve your trip now and get ready to tick another place off your must-visit list.

Why should I purchase my Windsor Hills vacation package with Travelocity?

Incredible savings, loads of thrilling destinations and 24/7 customer service you can rely on --- that's why. And with our Price Match Guarantee, you can rest easy knowing that you'll always get the best possible deal with Travelocity.

Can I save on my Windsor Hills car rental if I bundle it with hotels and flights?

Sure can --- and if you also add a tour or an experience to your Windsor Hills vacation package, you'll pick up even more savings. With an affordable package from Travelocity, you can find things to do in the region that are just right for you. Then, jump in your rental car and work your way through the list. Daytona International Speedway is one must-see sight to key into your GPS. It's 70 mi from Windsor Hills.