Windsor Hills Vacation Packages from $297

Windsor Hills flight + hotel vacation packages

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

Palazzo Lakeside Hotel

per person

Jul 29 - Aug 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This hotel features an outdoor pool, a gym, and a restaurant. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a picnic area are also on offer.

Westgate Palace Hotel / Universal / I-Drive

Florida Center

per person

Jun 24 - Jun 30

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 Lakes Resort & Spa Universal Studios Area

Save 100% on your flight

per person

Jul 11 - Jul 16

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Orlando (MCO)

This smoke-free hotel features a full-service spa, a water park, and a marina. There's fun for all ages with a lazy river and a children's club, and barbecue grills are available on site. Enjoy the 7 outdoor pools and get free valet parking.

Magic Moment Resort and Kids Club

Save 100% on your flight

per person

Jul 9 - Jul 15

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This hotel features an outdoor pool, a 24-hour gym, and a restaurant. There's fun for all ages with a theme park shuttle and a playground, and families will appreciate the onsite laundry facilities. There's no skimping on freebies - guests receive free breakfast, free WiFi, and free self parking.

Westgate Vacation Villas Resort

Save 100% on your flight

per person

Jul 29 - Aug 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to Orlando (MCO)

This smoke-free resort features a water park, a marina, and 4 restaurants. There's fun for all ages with a children's club and a children's pool, and families will appreciate the onsite laundry facilities. Enjoy the 14 outdoor pools and get free self parking.

Top Windsor Hills hotel deals

Free Waterpark, Free Heated Pool/Spa and Grill, Game/Theater Rm, & 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 barbecue grills are available on site. Enjoy the gym and perks like free WiFi.

Vibrant Townhome near parks!

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.

3BD/2BA Comfy Updated Condo Near Disney

Get rates

This condo features a gym and a spa tub.

Our DisneyDreamVilla - Salt water pool! Only minutes to DisneyWorld!!!

Get rates

A water park and an outdoor pool are featured at this smoke-free villa. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the spa tub and conveniences like a garden and concierge services.

Top-Rated Amazing Villa! Salt💧Pool, Game Room + Pool Heat, BBQ & Baby Gear

Get rates

Hot Tub

Pet friendly

Free Waterpark, Free Heated Pool/Spa and Grill, Game/Theater Rm, & PS5

Get rates

Hot Tub

Pool

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 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.

Photos of local treasures

Frequently asked questions

How much are vacation packages to Windsor Hills?

Travelocity provides package deals to Windsor Hills, as well as flights and hotels, starting from as low as $297. With all the extra money, you could book some interesting tours or maybe tack on some extra nights to your exciting adventure.

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

Travelocity has all you need to score a terrific Windsor Hills package deal. Select from 400 air carriers and 1,000,000 properties around the world and create a travel itinerary that suits your style. With so much choice, it’s time to start planning your next great adventure.

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

With our Price Match Guarantee, we’ll match any cheaper price you find. Add on our 24/7 customer support and exceptional service and the vacation you’ve been dreaming of is well within reach.

Can I save on my Windsor Hills car rental if I bundle it with a hotel or flight?

You sure can — and if you also add a tour to your Windsor Hills vacation package, you’ll save even more. With one of our packages, you can find things to do in the region that are right for you. Then, hop in your rental car and work your way through the list. Daytona International Speedway is one fantastic sight to take a look at. You’ll find it 70 mi from Windsor Hills.

What is the best time of year to go to Windsor Hills?

You’ll land the best hotel prices in and pay the highest prices in . You can expect it to be more relaxed in February, July and October, while you’ll have plenty more fellow visitors to meet during the months of March, April and June. It all depends on how much you’re willing to spend, the climate and how well you deal with crowds.