Cheap Vacations in Windsor Hills

Choose two or more items and save on your trip:

Windsor Hills vacations

Price found within the past 48 hours. Click for updated prices.
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
Price was $817, price is now $361 per person
$361
per person
Apr 11 - Apr 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was $1,436, price is now $589 per person
$589
per person
Apr 11 - Apr 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,232, price is now $653 per person
$653
per person
Apr 30 - May 3
just found
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Save 100% on your flight
Price was $1,572, price is now $969 per person
$969
per person
Apr 11 - Apr 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
Price was $1,121, price is now $702 per person
$702
per person
Apr 11 - Apr 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Reunion Resort & Golf Club

Reunion Resort & Golf Club

5 out of 5
Reunion
Save 100% on your flight
Price was $1,071, price is now $692 per person
$692
per person
Apr 11 - Apr 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Lake Buena Vista Resort Village & Spa

Lake Buena Vista Resort Village & Spa

4 out of 5
Save 100% on your flight
Price was $1,007, price is now $665 per person
$665
per person
Apr 11 - Apr 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Sonesta Essential Orlando Airport

Sonesta Essential Orlando Airport

3 out of 5
Save 100% on your flight
Price was $705, price is now $468 per person
$468
per person
Apr 11 - Apr 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Legacy Vacation Resorts - Kissimmee/Orlando

Legacy Vacation Resorts - Kissimmee/Orlando

3.5 out of 5
Save 100% on your flight
Price was $556, price is now $370 per person
$370
per person
Apr 11 - Apr 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)

3-night Windsor Hills vacations

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

Parkway International Resort

3 out of 5
Save 100% on your flight
Price was $408, price is now $292 per person
$292
per person
Apr 13 - Apr 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Save 100% on your flight
Price was $1,232, price is now $653 per person
$653
per person
Apr 30 - May 3
just found
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was $690, price is now $430 per person
$430
per person
Apr 21 - Apr 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was $677, price is now $451 per person
$451
per person
Apr 23 - Apr 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Hilton Garden Inn Jacksonville Ponte Vedra Sawgrass

Hilton Garden Inn Jacksonville Ponte Vedra Sawgrass

3 out of 5
Save 100% on your flight
Price was $570, price is now $388 per person
$388
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
Westgate Blue Tree Resort in Lake Buena Vista

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5
Price was $533, price is now $365 per person
$365
per person
Apr 30 - May 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Price was $753, price is now $531 per person
$531
per person
Apr 9 - Apr 12
found 1 day ago
Roundtrip flight included
Islip (ISP) to Orlando (MCO)
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
Price was $586, price is now $430 per person
$430
per person
Apr 21 - Apr 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
The Kenwood Inn

The Kenwood Inn

3.5 out of 5
Save 100% on your flight
Price was $1,016, price is now $755 per person
$755
per person
Apr 17 - Apr 20
found 22 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Price was $1,115, price is now $835 per person
$835
per person
Apr 19 - Apr 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)

4-night Windsor Hills vacations

Price found within the past 48 hours. Click for updated prices.
Westgate Blue Tree Resort in Lake Buena Vista

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5
Price was $619, price is now $392 per person
$392
per person
Apr 24 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was $1,910, price is now $974 per person
$974
per person
Apr 7 - Apr 11
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
Price was $843, price is now $478 per person
$478
per person
Apr 19 - Apr 23
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
Price was $701, price is now $431 per person
$431
per person
Apr 24 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was $756, price is now $477 per person
$477
per person
Apr 19 - Apr 23
found 2 days ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
The Shores Resort & Spa

The Shores Resort & Spa

4 out of 5
Save 100% on your flight
Price was $663, price is now $442 per person
$442
per person
Apr 15 - Apr 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Grand Seas MOD Collection by Sonesta

Grand Seas MOD Collection by Sonesta

3.5 out of 5
Save 100% on your flight
Price was $581, price is now $399 per person
$399
per person
Apr 15 - Apr 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Bahama House

Bahama House

3 out of 5
Save 100% on your flight
Price was $718, price is now $495 per person
$495
per person
Apr 15 - Apr 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Hard Rock Hotel Daytona Beach

Hard Rock Hotel Daytona Beach

4 out of 5
Save 100% on your flight
Price was $623, price is now $436 per person
$436
per person
Apr 15 - Apr 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
The Resort on Cocoa Beach

The Resort on Cocoa Beach

3.5 out of 5
Price was $1,256, price is now $882 per person
$882
per person
Apr 16 - Apr 20
found 8 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)

5-night Windsor Hills vacations

Price found within the past 48 hours. Click for updated prices.
Villa 1565

Villa 1565

3 out of 5
Price was $486, price is now $329 per person
$329
per person
Apr 25 - Apr 30
just found
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
Price was $1,037, price is now $504 per person
$504
per person
Apr 21 - Apr 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
Price was $856, price is now $484 per person
$484
per person
Apr 21 - Apr 26
found 10 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
Price was $934, price is now $617 per person
$617
per person
Apr 21 - Apr 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Blue Tree Resort in Lake Buena Vista

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5
Price was $839, price is now $562 per person
$562
per person
Apr 21 - Apr 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
The Kenwood Inn

The Kenwood Inn

3.5 out of 5
Price was $1,113, price is now $751 per person
$751
per person
Apr 25 - Apr 30
just found
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Sonesta Essential Orlando Airport

Sonesta Essential Orlando Airport

3 out of 5
Save 100% on your flight
Price was $656, price is now $448 per person
$448
per person
Apr 16 - Apr 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was $521, price is now $356 per person
$356
per person
Apr 16 - Apr 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
Westgate Leisure Resort

Westgate Leisure Resort

3.5 out of 5
Save 100% on your flight
Price was $583, price is now $399 per person
$399
per person
Apr 26 - May 1
found 18 hours ago
Roundtrip flight included
New York (NYC) to Orlando (MCO)
Harbor Island Beach Club by Villatel

Harbor Island Beach Club by Villatel

2 out of 5
Save 100% on your flight
Price was $2,096, price is now $1,444 per person
$1,444
per person
Apr 20 - Apr 25
found 9 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Hilton Garden Inn Jacksonville Ponte Vedra Sawgrass

Hilton Garden Inn Jacksonville Ponte Vedra Sawgrass

3 out of 5
Price was $1,124, price is now $777 per person
$777
per person
Apr 20 - Apr 25
found 7 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
The Local - St. Augustine

The Local - St. Augustine

2 out of 5
Price was $537, price is now $375 per person
$375
per person
Apr 25 - Apr 30
just found
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

6-7 night Windsor Hills vacations

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

Westgate Towers Resort

3.5 out of 5
Save 100% on your flight
Price was $662, price is now $314 per person
$314
per person
Apr 12 - Apr 18
found 14 hours ago
Roundtrip flight included
Philadelphia (PHL) to Orlando (MCO)
Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Price was $1,436, price is now $589 per person
$589
per person
Apr 11 - Apr 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
Price was $817, price is now $361 per person
$361
per person
Apr 11 - Apr 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Blue Tree Resort in Lake Buena Vista

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5
Save 100% on your flight
Price was $896, price is now $498 per person
$498
per person
Apr 4 - Apr 11
found 7 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
The Shores Resort & Spa

The Shores Resort & Spa

4 out of 5
Save 100% on your flight
Price was $2,033, price is now $1,171 per person
$1,171
per person
Apr 11 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
Hilton Garden Inn Jacksonville Ponte Vedra Sawgrass

Hilton Garden Inn Jacksonville Ponte Vedra Sawgrass

3 out of 5
Save 100% on your flight
Price was $1,116, price is now $672 per person
$672
per person
Apr 22 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Save 100% on your flight
Price was $1,572, price is now $969 per person
$969
per person
Apr 11 - Apr 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
Price was $1,121, price is now $702 per person
$702
per person
Apr 11 - Apr 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Grand Seas MOD Collection by Sonesta

Grand Seas MOD Collection by Sonesta

3.5 out of 5
Save 100% on your flight
Price was $990, price is now $624 per person
$624
per person
Apr 11 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)

Flight deals to Windsor Hills

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Wed, Apr 22 - Sat, Apr 25
PHL
Philadelphia
MCO
Orlando
$66 Roundtrip, found 5 days ago
$66
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, Apr 22 from Philadelphia to Orlando, returning Sat, Apr 25, priced at $66 found 5 days ago
Mon, May 11 - Tue, May 12
LGA
New York
MCO
Orlando
$70 Roundtrip, found 1 day ago
$70
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, May 11 from New York to Orlando, returning Tue, May 12, priced at $70 found 1 day ago
Tue, May 5 - Sat, May 9
EWR
New York
MCO
Orlando
$76 Roundtrip, found 23 hours ago
$76
Roundtrip
found 23 hours ago
Select Frontier Airlines flight, departing Tue, May 5 from New York to Orlando, returning Sat, May 9, priced at $76 found 23 hours ago

Top rated hotels for your Windsor Hills vacation

Windsor Hills Condo w/all things Mickey. Pool/Waterpark and minutes from Disney!

Windsor Hills Condo w/all things Mickey. Pool/Waterpark and minutes from Disney!

Kissimmee FL
0.24 mi from Windsor Hills
Get rates
With a stay at this condo, you'll be centrally located in Kissimmee, within a 10-minute drive of Walt Disney World® Resort and Old Town.
6/4 Home Pool/Spa Close to Disney, Free Water Park Use, Game RMThemed, WIFI BBQ

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

Kissimmee FL
0.2 mi from Windsor Hills
Get rates
With a stay at this vacation home, you'll be centrally located in Kissimmee, within a 10-minute drive of Walt Disney World® Resort and Mystic Dunes Golf Club.
Pool
Hot Tub
Top-Rated Amazing Villa! Salt💧Pool, Game Room + Pool Heat, BBQ & Baby Gear

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

Kissimmee FL
0.09 mi from Windsor Hills
$548 nightly
The price is $613 total per night
$613 total
Mar 6 - Mar 7
Total with taxes and fees
With a stay at this vacation home in Kissimmee (Windsor Hills), you'll be within a 10-minute drive of Walt Disney World® Resort and Old Town.
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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.