
$37 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 $37 One Way, $66 Round Trip from Boston to Windermere
Prices starting at $66 for return flights and $37 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

Boardwalk Inn and Suites
Mar 1 - Mar 5
Boston (BOS) to Orlando (MCO)
Reviewed on Dec 3, 2025

The Shores Resort & Spa
Feb 26 - Mar 4
Boston (BOS) to Orlando (MCO)
Reviewed on Sep 20, 2025

Parkway International Resort
Feb 26 - Mar 4
Boston (BOS) to Orlando (MCO)
Reviewed on Nov 17, 2025
Windermere first class flight packages

Westgate Town Center Resort
Feb 6 - Feb 9
Boston (BOS) to Orlando (MCO)
Reviewed on Apr 6, 2025

Margaritaville Cottages Orlando with H2O Waterpark by Vstays
Feb 6 - Feb 9
Boston (BOS) to Orlando (MCO)
Reviewed on Oct 7, 2024

Reunion Resort & Golf Club
Feb 6 - Feb 9
Boston (BOS) to Orlando (MCO)
Reviewed on Oct 15, 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
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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.


