
$33 Cheap flight deals from Boston (BOS) to Windermere (ORL)
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This Weekend's Flight Deals from Boston to Windermere
This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Airfares from $33 One Way, $62 Round Trip from Boston to Windermere
Prices starting at $62 for return flights and $33 for one-way flights to Windermere were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Windermere economy flight packages

Palazzo Lakeside Hotel
Feb 26 - Mar 1
Boston (BOS) to Orlando (MCO)
Orlando (MCO) to Boston (BOS)
Reviewed on Dec 27, 2025

Westgate Town Center Resort
Feb 26 - Mar 4
Boston (BOS) to Orlando (MCO)
Reviewed on Apr 6, 2025

Westgate Cocoa Beach Resort
Mar 1 - Mar 6
Boston (BOS) to Orlando (MCO)
Orlando (MCO) to Boston (BOS)
Reviewed on Oct 5, 2025
Windermere first class flight packages

The Delaney Hotel
Feb 20 - Feb 24
Boston (BOS) to Orlando (MCO)
Reviewed on Jul 8, 2025

Evermore Orlando Resort
Feb 20 - Feb 24
Boston (BOS) to Orlando (MCO)
Reviewed on Oct 24, 2025

Villatel Orlando Resort
Feb 20 - Feb 24
Boston (BOS) to Orlando (MCO)
Reviewed on Feb 3, 2025
More About Flying To Windermere from Boston
Route Information for Flights from Boston to Windermere
Origin Airport IATA Code | BOS |
|---|---|
Destination Airport IATA Code | ORL |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Boston to Windermere
Planning a trip is rarely straight forward, especially when searching for cheap deals. At Orbitz.com, we make it easier than anywhere else by providing you with guaranteed low prices. So if you are looking for Boston to Windermere flights at low cost, you will not be disappointed.
Cruising for a bargain deal
Regardless of your destination, we always provide you fantastic bargains for your trip, and that includes on hotels and even cruises. We offer budget air fares on flights from Boston to Windermere so you can reach your destination with more money in your pocket to spend.
Cheap Boston to Windermere flights that lead to rewards
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Quality combinations
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Even last minute bookings on our apps
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Flights from Boston
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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.



