Cheap Vacations in Windsor Hills

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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 $501, price is now $276 per person
$276
per person
Apr 30 - May 3
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Save 100% on your flight
Price was $595, price is now $293 per person
$293
per person
Apr 15 - Apr 20
found 15 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was $714, price is now $362 per person
$362
per person
Apr 18 - Apr 25
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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
International Drive District
Price was $629, price is now $381 per person
$381
per person
Apr 12 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Orlando (MCO)
Lake Buena Vista Resort Village & Spa

Lake Buena Vista Resort Village & Spa

4 out of 5
Price was $1,200, price is now $765 per person
$765
per person
Apr 18 - Apr 25
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was $656, price is now $426 per person
$426
per person
Apr 18 - Apr 25
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Alhambra Villas

Alhambra Villas

3 out of 5
Solivita
Save 100% on your flight
Price was $994, price is now $648 per person
$648
per person
Apr 6 - Apr 12
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
Price was $2,011, price is now $1,333 per person
$1,333
per person
Apr 18 - Apr 25
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)

3-night Windsor Hills vacations

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

Seasons Florida Resort

2 out of 5
Price was $396, price is now $263 per person
$263
per person
May 1 - May 4
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
Price was $501, price is now $276 per person
$276
per person
Apr 30 - May 3
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Save 100% on your flight
Price was $671, price is now $399 per person
$399
per person
Apr 30 - May 3
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Grand Seas MOD Collection by Sonesta

Grand Seas MOD Collection by Sonesta

3.5 out of 5
Price was $466, price is now $308 per person
$308
per person
Apr 11 - Apr 14
found 1 day ago
Roundtrip flight included
New York (NYC) 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 $499, price is now $342 per person
$342
per person
Apr 5 - Apr 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
The Fold Hotels Orlando

The Fold Hotels Orlando

2 out of 5
Save 100% on your flight
Price was $701, price is now $484 per person
$484
per person
Apr 16 - Apr 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 $640, price is now $452 per person
$452
per person
Apr 8 - Apr 11
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Reunion Resort & Golf Club

Reunion Resort & Golf Club

5 out of 5
Save 100% on your flight
Price was $643, price is now $467 per person
$467
per person
Apr 30 - May 3
found 1 day ago
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 $1,144, price is now $838 per person
$838
per person
Apr 16 - Apr 19
found 21 hours ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Wyndham Grand Orlando Resort Bonnet Creek

Wyndham Grand Orlando Resort Bonnet Creek

4 out of 5
Price was $692, price is now $516 per person
$516
per person
Apr 16 - Apr 19
found 21 hours ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)

4-night Windsor Hills vacations

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

Alhambra Villas

3 out of 5
Price was $364, price is now $245 per person
$245
per person
Apr 13 - Apr 17
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was $580, price is now $284 per person
$284
per person
Apr 16 - Apr 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Extended Stay America Suites Orlando Conv Ctr Universal Blvd

Extended Stay America Suites Orlando Conv Ctr Universal Blvd

2.5 out of 5
Save 100% on your flight
Price was $1,119, price is now $555 per person
$555
per person
Apr 30 - May 4
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 $629, price is now $381 per person
$381
per person
Apr 12 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Orlando (MCO)
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was $446, price is now $274 per person
$274
per person
Apr 11 - Apr 15
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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 $1,250, price is now $791 per person
$791
per person
Apr 13 - Apr 17
found 1 hour ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Bryan’s Spanish Cove

Bryan’s Spanish Cove

3 out of 5
Save 100% on your flight
Price was $562, price is now $371 per person
$371
per person
Apr 10 - Apr 14
found 12 hours ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
The Delaney Hotel

The Delaney Hotel

3.5 out of 5
Price was $869, price is now $593 per person
$593
per person
Apr 12 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Orlando (MCO)
Costa d'Este Beach Resort and Spa

Costa d'Este Beach Resort and Spa

4 out of 5
Save 100% on your flight
Price was $939, price is now $647 per person
$647
per person
Apr 29 - May 3
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was $386, price is now $269 per person
$269
per person
Apr 11 - Apr 15
found 1 day ago
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
Price was $1,127, price is now $796 per person
$796
per person
Apr 11 - Apr 15
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)

5-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 $595, price is now $293 per person
$293
per person
Apr 15 - Apr 20
found 15 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Extended Stay America Suites Orlando Conv Ctr Universal Blvd

Extended Stay America Suites Orlando Conv Ctr Universal Blvd

2.5 out of 5
Price was $1,402, price is now $553 per person
$553
per person
Apr 30 - May 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
Price was $707, price is now $330 per person
$330
per person
Apr 15 - Apr 20
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Price was $961, price is now $463 per person
$463
per person
Apr 18 - Apr 23
found 1 day ago
Roundtrip non-stop 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 $1,090, price is now $602 per person
$602
per person
Apr 6 - Apr 11
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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 $687, price is now $384 per person
$384
per person
Apr 18 - Apr 23
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
The Shores Resort & Spa

The Shores Resort & Spa

4 out of 5
Save 100% on your flight
Price was $652, price is now $370 per person
$370
per person
Apr 12 - Apr 17
found 1 day ago
Roundtrip flight included
New York (JFK) to Orlando (MCO)
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Save 100% on your flight
Price was $528, price is now $320 per person
$320
per person
Apr 9 - Apr 14
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Boardwalk Inn and Suites

Boardwalk Inn and Suites

2.5 out of 5
Save 100% on your flight
Price was $512, price is now $317 per person
$317
per person
Apr 12 - Apr 17
found 1 day ago
Roundtrip flight included
New York (JFK) to Orlando (MCO)
Lake Buena Vista Resort Village & Spa

Lake Buena Vista Resort Village & Spa

4 out of 5
Price was $845, price is now $556 per person
$556
per person
Apr 12 - Apr 17
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Orlando (MCO)
Westgate Leisure Resort

Westgate Leisure Resort

3.5 out of 5
Save 100% on your flight
Price was $523, price is now $344 per person
$344
per person
Apr 26 - May 1
found 1 day ago
Roundtrip flight included
New York (NYC) to Orlando (MCO)

6-7 night Windsor Hills vacations

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

Orlando Palms Hotel

2.5 out of 5
Save 100% on your flight
Price was $531, price is now $346 per person
$346
per person
Apr 9 - Apr 15
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
Price was $1,640, price is now $640 per person
$640
per person
Apr 11 - Apr 18
found 1 day ago
Roundtrip flight included
New York (JFK) to Orlando (MCO)
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was $714, price is now $362 per person
$362
per person
Apr 18 - Apr 25
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
Price was $1,079, price is now $553 per person
$553
per person
Apr 5 - Apr 11
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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 $786, price is now $434 per person
$434
per person
Apr 11 - Apr 17
found 24 hours ago
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 $1,334, price is now $810 per person
$810
per person
Apr 11 - Apr 18
found 1 day ago
Roundtrip flight included
New York (JFK) 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
Save 100% on your flight
Price was $1,165, price is now $733 per person
$733
per person
Apr 6 - Apr 12
just found
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Lake Buena Vista Resort Village & Spa

Lake Buena Vista Resort Village & Spa

4 out of 5
Price was $1,200, price is now $765 per person
$765
per person
Apr 18 - Apr 25
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was $656, price is now $426 per person
$426
per person
Apr 18 - Apr 25
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Alhambra Villas

Alhambra Villas

3 out of 5
Save 100% on your flight
Price was $994, price is now $648 per person
$648
per person
Apr 6 - Apr 12
just found
Roundtrip flight included
Detroit (DTW) to Orlando (MCO)
Villa 1565

Villa 1565

3 out of 5
Save 100% on your flight
Price was $538, price is now $355 per person
$355
per person
Apr 25 - May 1
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 - Wed, Apr 29
LGA
New York
MCO
Orlando
$56 Roundtrip, found 2 hours ago
$56
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Wed, Apr 22 from New York to Orlando, returning Wed, Apr 29, priced at $56 found 2 hours ago
Mon, Apr 20 - Wed, Apr 22
TTN
Trenton
MCO
Orlando
$68 Roundtrip, found 3 hours ago
$68
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Mon, Apr 20 from Trenton to Orlando, returning Wed, Apr 22, priced at $68 found 3 hours ago
Tue, Apr 28 - Wed, Apr 29
PHL
Philadelphia
MCO
Orlando
$70 Roundtrip, found 3 days ago
$70
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Apr 28 from Philadelphia to Orlando, returning Wed, Apr 29, priced at $70 found 3 days 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.
Pool
Kitchen
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
$863 nightly
The price is $965 total per night
$965 total
Apr 3 - Apr 4
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
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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.