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Windsor Hills Vacation Packages

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Windsor Hills Vacation: Coronavirus Information

Most Windsor Hills hotels offer free cancellation. Consider booking refundable hotels rather than non-refundable ones. Just look for the ‘free cancellation’ message during your hotel search. Prices can vary, but right now we believe that flexibility matters.

For more information about the impact of COVID-19 on your Windsor Hills trip, please visit our Coronavirus Information page (opens in new window).

Top Vacation Package Deals in Windsor Hills

Hyatt Regency Orlando

Hyatt Regency Orlando

4.5 out of 5
Save 100% on your flight$502

$309

per person
Jan 15 - Jan 18
Roundtrip flight included
Newark (EWR) to Orlando (ORL)
4.5/5Wonderful! (2,053 reviews)

"Everything! I have no complaints about this hotel.…"

Reviewed on Oct 30, 2020

Fairfield Inn & Suites Lake Buena Vista in Marriott Village

Fairfield Inn & Suites Lake Buena Vista in Marriott Village

3 out of 5
Save 100% on your flight$503

$336

per person
Dec 26 - Dec 30
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
4.3/5Excellent! (1,368 reviews)

"Spacious room, got a free upgrade from a room with 1 bed to a room with 1 king bed and a set of bunk beds (we didn’t need the bunk beds but it added lots of extra space); parking costs extra which is strange for a hotel…"

Reviewed on Mar 14, 2020

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight$432

$300

per person
Dec 18 - Dec 23
Roundtrip flight included
Boston (BOS) to Orlando (ORL)
3.9/5Good! (3,330 reviews)

"The property was nice there was an alligator in the lake. We didn’t have shuttles to anywhere not even the airport. Drafts at the front of the property was open the service we got there was terrible we ended up leaving there without eating and they were not busy. The waitress/server we had was so rude she got our drinks wrong and when we said we were ready to order food she told us we were to have to wait. We left without eating paid for our drinks and left.…"

Reviewed on Oct 26, 2020

The Ritz-Carlton Orlando, Grande Lakes

The Ritz-Carlton Orlando, Grande Lakes

5 out of 5
Save 100% on your flight$1,384

$962

per person
Jan 25 - Jan 29
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
4.6/5Wonderful! (999 reviews)

"The Ritz needs an adult only pool besides the spa pool that is reserved for spa guests only.…"

Reviewed on Mar 18, 2020

Quality Inn & Suites Heritage Park

Quality Inn & Suites Heritage Park

2.5 out of 5
$280

$200

per person
Dec 13 - Dec 18
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
4.1/5Very Good! (559 reviews)

"Extremely clean room and bathroom. Large room, plenty of room, comfortable bed and pillows. Free parking and limited breakfast. Would definitely recommend and go back.…"

Reviewed on Sep 21, 2020

2021 Windsor Hills vacation deals

Hyatt Regency Orlando

Hyatt Regency Orlando

4.5 out of 5
Save 100% on your flight$502

$309

per person
Jan 15 - Jan 18
Roundtrip flight included
Newark (EWR) to Orlando (ORL)
4.5/5Wonderful! (2,053 reviews)

"Everything! I have no complaints about this hotel.…"

Reviewed on Oct 30, 2020

B Resort & Spa in the Disney Springs Resort Area™

B Resort & Spa in the Disney Springs Resort Area™

4 out of 5
Save 100% on your flight$465

$291

per person
Feb 14 - Feb 18
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
3.9/5Good! (3,636 reviews)

"It was a nice hotel and the Lobby was nice and smelled really good but the hallways and rooms did not! And the bathroom wasn’t very clean. The pillows were awful too.…"

Reviewed on Oct 30, 2020

Fantasy World Resort

Fantasy World Resort

3.5 out of 5
Save 100% on your flight$465

$305

per person
Feb 14 - Feb 18
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
4.2/5Very Good! (3,430 reviews)

"Nice place. I love the washer and dryer. The king bed could be changed it was very worn out. However the rest of the place was very nice.…"

Reviewed on Oct 27, 2020

Summer Bay Orlando by Exploria Resorts

Summer Bay Orlando by Exploria Resorts

3.5 out of 5
West Kissimmee
$472

$321

per person
Feb 4 - Feb 11
Roundtrip flight included
Boston (BOS) to Orlando (ORL)
4.1/5Very Good! (2,707 reviews)

"The property was huge and fun people were nice loved it loved it we will do it again…"

Reviewed on Oct 1, 2020

The Ritz-Carlton Orlando, Grande Lakes

The Ritz-Carlton Orlando, Grande Lakes

5 out of 5
Save 100% on your flight$1,658

$1,134

per person
Feb 14 - Feb 18
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
4.6/5Wonderful! (999 reviews)

"The Ritz needs an adult only pool besides the spa pool that is reserved for spa guests only.…"

Reviewed on Mar 18, 2020

Top Hotels in Windsor Hills

3 BR 2 Miles to Disney, Pool, Spa, Water Park, Game Room, Free Wifi and More
3 BR 2 Miles to Disney, Pool, Spa, Water Park, Game Room, Free Wifi and More
Kissimmee, FL
4.6/5Exceptional! (49 reviews)
Nice Stay

"As advertised!"…"

Reviewed on Oct 29, 2020

3 BR 2 Miles to Disney, Pool, Spa, Water Park, Game Room, Free Wifi and More
Dream Disney Family Vacation, Best Resort, 2 Miles To Disney, Space For 10
Dream Disney Family Vacation, Best Resort, 2 Miles To Disney, Space For 10
Kissimmee, FL
4.6/5Exceptional! (49 reviews)
Perfect for our family trip

"Very roomy, the kids loved the pool and slides!"…"

Reviewed on Sep 14, 2020

Dream Disney Family Vacation, Best Resort, 2 Miles To Disney, Space For 10
5-10 Min. To Disney - Gated Resort With Large Heated Pool And Slide
5-10 Min. To Disney - Gated Resort With Large Heated Pool And Slide
Kissimmee, FL
4.8/5Exceptional! (28 reviews)
Great location

"Clean, comfortable and very close to Disney! We (family) loved our 4 day weekend at this beautiful condo. The condo was clean and had everything we needed!"…"

Reviewed on Sep 7, 2020

5-10 Min. To Disney - Gated Resort With Large Heated Pool And Slide
See all 2443 properties in Windsor Hills
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.

Top things to do in Windsor Hills

Image for Universal Orlando Resort Theme Park Tickets

Universal Orlando Resort Theme Park Tickets

$140
Per adult
86% of travellers recommend
Universal Orlando Resort Theme Park Tickets
Image for SeaWorld Parks and Resorts Theme Parks Tickets

SeaWorld Parks and Resorts Theme Parks Tickets

$39
Per adult
82% of travellers recommend
SeaWorld Parks and Resorts Theme Parks Tickets
Image for LEGOLAND® Florida Tickets

LEGOLAND® Florida Tickets

$91
Per adult
82% of travellers recommend
LEGOLAND® Florida Tickets
See all activities in Orlando

Frequently asked questions

How much does a Windsor Hills vacation package cost?
Starting from a low $200, a vacation package is your gateway to affordable travel. Custom make your Windsor Hills trip by selecting from our wide range of hotels, airfares and rental cars.
If I'm not able to travel, can I cancel my Windsor Hills vacation package?
If you’ve chosen a Windsor Hills vacation package, you can change or cancel it, but you may incur a charge depending on the situation. You may be able to cancel and rebook at no cost if you’ve locked in your package in the last 24 hours. If it’s been longer than that, you may incur additional charges from your hotel, airline or car rental company. If you suddenly need to change your plans, make our Customer Service Portal your first stop for more info.
How do I get a cheap travel package to Windsor Hills?
It’s easy. Just bundle everything together. Hotels, rental cars and flights — combine whatever you need into a Windsor Hills vacation package and save as much as $583. Score even more discounts when you add extras such as tours or experiences to your booking. But here’s the impressive part. You have the flexibility to put together your vacation your way. We offer more than 550 air carriers and 1,000,000 hotel options all over the world, so that everyone has an opportunity to travel and fulfill those vacation fantasies.
What are the top hotels in Windsor Hills?
Secure a room at Windsor Hills Resort by Global Resort Homes. It’s one of the neighborhood’s most sought-after hotels. Another top-rated option in Windsor Hills is Windsor Hills by FunQuest Vacation.
When is the best time of year to visit Windsor Hills?
That depends on what’s important to you. If you want to score the best deal, visit in . Airfares and hotels are generally cheaper around this time of year than they are in . If you’d like to experience the buzz of Windsor Hills in the peak season, lock in your escape for . is typically a quieter time of year.
How far in advance should I book my Windsor Hills vacation?
While not all air carriers advertise ticket prices early, you can normally compare international flights on Expedia up to 12 months in advance. This is the time when you’ll bag some incredible deals. If you’ve left everything to the last minute, you might still be in luck. Low prices occasionally become available only weeks prior to departure.
What does an Expedia Windsor Hills travel package include?
It comes down to what you’re after. If you’re traveling alone, you might decide to combine flights and hotels. Bringing the whole crew to Windsor Hills? A travel package including hotels, flights and rental cars might suit you better. Expedia gives you the flexibility and freedom to customize your travel package.
What should I know before booking a Windsor Hills travel package?
So many places to go, so many things to see and do. With a travel package, you can tick more of them off your list. Bundle your hotels, rental cars and flights and make big savings.
Does Expedia offer Book Now, Pay Later Windsor Hills vacation packages?
Expedia has partnered with online lender Affirm to help ease any financial stress related to your trip. This may be useful if your need to travel has cropped up suddenly. Book Now, Pay Later and spread the price of your activities and hotel package booking over a number of payments.
Can I choose my airline with a Windsor Hills Expedia vacation package?
You can, and with over 550 airlines to choose from worldwide, you’ve got lots of choice. Browse the available options and find out which airline suits your budget and needs.