Windsor Hills Vacation Packages 2026 from $287

Windsor Hills flight + hotel vacation packages

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

Seasons Florida Resort

Save 100% on your flight

$287

per person

Sep 20 - Sep 25

found 2 days ago

Roundtrip flight included

Hartford (BDL) to Orlando (MCO)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. An outdoor pool and laundry facilities are also provided.

Westgate Palace Hotel / Universal / I-Drive

International Drive District

$414

per person

Sep 6 - Sep 11

found 15 hours ago

Roundtrip non-stop 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 Towers Resort

Save 100% on your flight

$399

per person

Oct 3 - Oct 10

found 1 day ago

Roundtrip flight included

Hartford (BDL) to Orlando (MCO)

2 outdoor pools, 2 hot tubs, and a gym are all featured at this smoke-free hotel. There's fun for all ages with a children's pool and a playground, and barbecue grills are available on site. Relax with a drink at the bar/lounge and enjoy perks like free self parking.

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

International Drive District

$491

per person

Oct 14 - Oct 21

found 1 day ago

Roundtrip flight included

Hartford (BDL) to Orlando (MCO)

This hotel features an outdoor pool and a rooftop terrace. Enjoy the hot tub and free perks like continental breakfast and free self parking. A business center, free WiFi in public areas, and a terrace are also on offer.

WorldQuest Orlando Resort

Save 100% on your flight

$579

per person

Oct 3 - Oct 10

found 1 day ago

Roundtrip flight included

Hartford (BDL) to Orlando (MCO)

This aparthotel features an outdoor pool and a 24-hour gym. Families will appreciate the free theme park shuttle and onsite laundry facilities. Relax with a drink at the poolside bar and enjoy perks like free self parking and free WiFi.

Top Windsor Hills hotels deals

Magical Memories in Windsor Hills Resort

Four Corners FL

Get rates

This villa features an outdoor pool and a hot tub. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities.

Pool

Hot Tub

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

Kissimmee FL

Get rates

This vacation home features a gym and a hot tub. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. A garden and barbecue grills are also provided.

Pool

Hot Tub

Dream Disney Family Vacation, Best Resort, 2 Miles To Disney, Space For 8

Kissimmee FL

Get rates

This condo features laundry facilities.

Pool

Kitchen

SUNNY DISNEY ESCAPE: as close to Disney as you can get with the comforts of home

Kissimmee FL

Get rates

This condo features a gym and a hot tub. Families will appreciate the playground and barbecue grills. WiFi in public areas is free.

Pool

Hot Tub

Livin the Dream❤️Closest FREE Resort to Disney! 3 Kings

Kissimmee FL

$500 nightly

$558 total

Aug 18 - Aug 19

Total with taxes and fees

A water park and a hot tub are featured at this smoke-free vacation home. Families will appreciate the arcade/game room and onsite laundry facilities. Enjoy the gym and perks like free WiFi.

Pool

Hot Tub

Amazing 6-bedroom Villa with Private Pool Minutes from Disney! 5 Star Theming!

Kissimmee FL

Get rates

This vacation home features an outdoor pool and a gym. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the hot tub and perks like free WiFi.

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.

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 $287. 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.