
Windsor Hills Vacation Packages
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Top Windsor Hills vacation package deals
Price found within the past 48 hours. Click for updated prices.

3.0-star property
Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive
International Drive District
8/10 Very Good! (122 reviews)
Dec 11 - Dec 16
5 night stay
Boston (BOS) to Orlando (MCO)
Breeze Airways • Non-stop • Coach
Orlando (MCO) to Boston (BOS)
Spirit Airlines • Non-stop • Coach
Save 100% on your flight
Price was $726, price is now $371 per person
$371
per person
found 1 day ago
The staff were super nice especially the lady at the front desk and the lady around the cocktail area. The hotel was nice and clean with a nice view it was walkable to Icon park and restaurants. Will stay there again.
Reviewed on Jul 31, 2025

4.0-star property
Westgate Town Center Resort
8/10 Very Good! (1,360 reviews)
Dec 23 - Dec 30
7 night stay
Boston (BOS) to Orlando (MCO)
Southwest Airlines • Non-stop • Coach
Orlando (MCO) to Boston (BOS)
Frontier Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,468, price is now $697 per person
$697
per person
found 1 day ago
We took our 3 year old nephew here and he had a BLAST! There is so much to do, we didn’t leave for 2 of the 3 days that we stayed.
He’s about 42 inches which got him on most of the slides but not all. Keep size in mind when booking for little ones because if they’re under 40in they’re limited to the slides.
He was a little bummed that he couldn’t do the pirates plunge (biggest slide) but there were enough distractions that it didn’t matter.
Also, the lazy river is great! Just be careful with the big kids, they tend to knock the little ones over or into the wall because they’re just running through it.
The water park is an extra fee FYI
There’s “ice” skating, swan paddle boats, water park, mini golf, a train trolly, restaurants, arcade, jungle gym, multiple pools. Definitely a good spot if you don’t want to do the parks every day that you’re there! Highly recommend.
Reviewed on Apr 6, 2025

4.0-star property
Westgate Cocoa Beach Resort
8.8/10 Excellent! (486 reviews)
Dec 25 - Jan 1
7 night stay
Boston (BOS) to Orlando (MCO)
Frontier Airlines • Roundtrip • Coach
Price was $3,135, price is now $1,493 per person
$1,493
per person
found 4 hours ago
Sue behind the bar was amazing. Hotel is a little dated and could use a new external color scheme. Rooms were modernized and mostly clean (sofa needs vacuumed) We had a great time and made use of all the pool areas and took advantage of happy hour every day. It is a bit of a walk from the main part of the resort to the beach so keep that in mind. Great place for family relaxing
Reviewed on Oct 5, 2025

4.0-star property
Summerville Vacation Homes by Columbia Management
8.4/10 Very Good! (151 reviews)
Dec 23 - Dec 30
7 night stay
Boston (BOS) to Orlando (MCO)
Southwest Airlines • Non-stop • Coach
Orlando (MCO) to Boston (BOS)
Frontier Airlines • Non-stop • Coach
Price was $2,509, price is now $1,226 per person
$1,226
per person
found 1 day ago
This concept is nicer than staying in a hotel room. The home was spacious and decorated very well. All necessities were provided. However, the ice maker in the refrigerator was not working. We were only there for 3 nights so I didn’t bother management with it.
Reviewed on Apr 19, 2021

5.0-star property
ette hotel
9.8/10 Exceptional! (336 reviews)
Jan 7 - Jan 13
6 night stay
Boston (BOS) to Orlando (MCO)
United • Non-stop roundtrip • Coach
Price was $1,818, price is now $914 per person
$914
per person
found 24 hours ago
Beautiful and very clean place to stay. We definitely will be back.
Reviewed on Sep 23, 2023
Top rated hotels for your Windsor Hills vacation package

6/4 Home Pool/Spa Close to Disney, Free Water Park Use, Game RMThemed, WIFI BBQ
0.2 mi from Windsor Hills
Guests staying at this vacation home enjoy access to a water park, a gym, and a hot tub. Other amenities at this family-friendly vacation home include an arcade/game room, laundry facilities, and barbecue grills.
Pool
Hot Tub

2 Bedroom, 2 Bath Condo 2 miles from Disney and 10 miles from Universal studios.
0.34 mi from Windsor Hills
At this condo, guests enjoy a water park, an outdoor pool, and a gym. Other amenities at this family-friendly condo building include a hot tub, an arcade/game room, and laundry facilities.
Pool
Hot Tub

Villa 7748 - Arcade Rm Updated Mar 2025! 3 mi from Disney, Pool Heat, BBQ & PS5
0.17 mi from Windsor Hills
Guests of this vacation home enjoy a water park, an outdoor pool, and a gym. Other amenities at this family-friendly vacation home include a hot tub, an arcade/game room, and laundry facilities.
Pool
Hot Tub
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.