Search Deals onWindsor Vacation Packages
Windsor Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Palazzo Lakeside Hotel
per person
May 6 - May 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this hotel in Kissimmee. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Old Town and Disney Springs™ are located nearby.
Westgate Palace Hotel / Universal / I-Drive
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 4-star family-friendly resort in Orlando. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Universal’s Volcano Bay and The Orlando Eye at ICON Park are located nearby.
Ocean Sands Beach Boutique Inn - 1 Acre Private Beach
per person
May 7 - May 13
found 23 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 3.5-star beach hotel in St. Augustine. Enjoy free breakfast, free WiFi, and a private beach. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Vilano Beach and Castillo de San Marcos National Monument are located nearby.
Westgate Vacation Villas Resort
Save 100% on your flight
per person
Jun 14 - Jun 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 4-star family-friendly resort in Kissimmee. Enjoy free parking, 14 outdoor pools, and 4 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Disney's Animal Kingdom® Theme Park and ESPN Wide World of Sports are located nearby.
Westgate Lakes Resort & Spa Universal Studios Area
Save 100% on your flight
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 4-star spa hotel in Orlando. Enjoy free parking, 7 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions The Wheel at ICON Park™ and Aquatica are located nearby.
Seasons Florida Resort
Save 100% on your flight
per person
May 22 - May 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
Book a stay at this business-friendly hotel in Kissimmee. Enjoy free WiFi, free parking, and laundry facilities. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Old Town and Disney Springs™ are located nearby.
Bryan’s Spanish Cove
Save 100% on your flight
per person
May 6 - May 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 3-star hotel in Orlando. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Disney Springs™ and Orlando Vineland Premium Outlets are located nearby.
Encore Resort and Water Park At Reunion by Rentyl
Save 100% on your flight
per person
Jun 4 - Jun 7
found 2 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
Stay at this 5-star luxury resort in Kissimmee. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions ESPN Wide World of Sports and Disney's Animal Kingdom® Theme Park are located nearby.
Windsor Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Windsor Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Tue, May 6 - Thu, May 8
LGA
LaGuardia
MCO
Orlando Intl.
$69 Roundtrip, found 1 day ago
$69
Roundtrip
found 1 day ago
Wed, Apr 9 - Tue, Apr 15
BOS
Logan Intl.
MCO
Orlando Intl.
$82 Roundtrip, found 1 day ago
$82
Roundtrip
found 1 day ago
Mon, May 12 - Thu, May 15
TTN
Mercer
MCO
Orlando Intl.
$84 Roundtrip, found 1 day ago
$84
Roundtrip
found 1 day ago
Wed, Jul 9 - Tue, Jul 15
PHL
Philadelphia Intl.
MCO
Orlando Intl.
$84 Roundtrip, found 1 day ago
$84
Roundtrip
found 1 day ago
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