$44 Cheap flight deals from Boston (BOS) to Windermere (ORL)

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

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.

Sat, Oct 11 - Wed, Oct 22
PSM
Portsmouth Intl.
MCO
Orlando Intl.
$177 Roundtrip, just found
$177
Roundtrip
just found
Select Breeze Airways flight, departing Sat, Oct 11 from Portsmouth Intl. to Orlando Intl., returning Wed, Oct 22, priced at $177 just found
Sat, Oct 11 - Wed, Oct 22
PSM
Portsmouth Intl.
MCO
Orlando Intl.
$177 Roundtrip, just found
$177
Roundtrip
just found
Select Breeze Airways flight, departing Sat, Oct 11 from Portsmouth Intl. to Orlando Intl., returning Wed, Oct 22, priced at $177 just found
Sun, Oct 12 - Sat, Oct 18
PVD
T.F. Green
MCO
Orlando Intl.
$285 Roundtrip, found 2 hours ago
$285
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Sun, Oct 12 from T.F. Green to Orlando Intl., returning Sat, Oct 18, priced at $285 found 2 hours ago
Sat, Oct 11 - Thu, Oct 23
ORH
Worcester Regional
MCO
Orlando Intl.
$351 Roundtrip, found 3 hours ago
$351
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Sat, Oct 11 from Worcester Regional to Orlando Intl., returning Thu, Oct 23, priced at $351 found 3 hours ago

Airfares from $44 One Way, $87 Round Trip from Boston to Windermere

Prices starting at $87 for return flights and $44 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.

Wed, Oct 29 - Sat, Nov 1
BOS
Boston
MCO
Orlando
$87 Roundtrip, found 5 hours ago
$87
Roundtrip
found 5 hours ago
Select Spirit Airlines flight, departing Wed, Oct 29 from Boston to Orlando, returning Sat, Nov 1, priced at $87 found 5 hours ago
Fri, Oct 31 - Sat, Nov 8
BOS
Boston
MCO
Orlando
$91 Roundtrip, found 3 hours ago
$91
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Fri, Oct 31 from Boston to Orlando, returning Sat, Nov 8, priced at $91 found 3 hours ago
Wed, Dec 10 - Wed, Dec 17
PSM
Portsmouth
MCO
Orlando
$102 Roundtrip, found 7 hours ago
$102
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Wed, Dec 10 from Portsmouth to Orlando, returning Wed, Dec 17, priced at $102 found 7 hours ago
Tue, Dec 9 - Fri, Dec 12
ORH
Worcester
MCO
Orlando
$103 Roundtrip, found 6 days ago
$103
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Tue, Dec 9 from Worcester to Orlando, returning Fri, Dec 12, priced at $103 found 6 days ago
Sat, Dec 13 - Wed, Dec 17
MHT
Manchester
MCO
Orlando
$122 Roundtrip, found 1 day ago
$122
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Dec 13 from Manchester to Orlando, returning Wed, Dec 17, priced at $122 found 1 day ago

Windermere economy flight packages

Price found within the past 48 hours. Click for updated prices.
Westgate Town Center Resort
4.0-star property

Westgate Town Center Resort

8/10 Very Good! (1,360 reviews)

Nov 6 - Nov 10

4 night stay

Boston (BOS) to Orlando (MCO)

Spirit Airlines • Non-stop • Coach

Orlando (MCO) to Boston (BOS)

Southwest Airlines • Non-stop • Coach
Save 100% on your flight
Price was $678, price is now $409 per person
$409
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

Westgate Palace Hotel / Universal / I-Drive
4.0-star property

Westgate Palace Hotel / Universal / I-Drive

8.8/10 Excellent! (1,012 reviews)

Nov 7 - Nov 10

3 night stay

Boston (BOS) to Orlando (MCO)

Spirit Airlines • Non-stop • Coach

Orlando (MCO) to Boston (BOS)

Southwest Airlines • Non-stop • Coach
Save 100% on your flight
Price was $762, price is now $432 per person
$432
per person
found 1 day ago
The location is conveniently close to Universal, with a nearby 7-Eleven and several restaurants. The room is clean and pleasant, and parking is easily accessible.

Reviewed on Aug 6, 2025

The Shores Resort & Spa
4.0-star property

The Shores Resort & Spa

9/10 Wonderful! (1,692 reviews)

Nov 5 - Nov 11

6 night stay

Boston (BOS) to Orlando (MCO)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $917, price is now $521 per person
$521
per person
found 1 day ago
Pretty hotel with nice layout and nice rooms. Great restaurant and friendly staff.

Reviewed on Sep 20, 2025

Don't see what you're looking for?
See all available trips from Boston to Windermere
View all trips

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

For the best travel experience from Boston to Windermere domestic and international travelers everywhere choose Orbitz for guaranteed low prices and cutting-edge mobile tools.

Convenient Low-Cost Travel

Orbitz makes it simple to book discount flights from Boston to {destination.name} without compromising your schedule. You can always find deals on domestic flights from a location near you. You may find the best deals to fit your schedule by mixing and matching airlines to get you from Boston to Windermere.

Access Orbitz On The Move

You can access Orbitz anywhere at anytime for travel from Boston to Windermere using the latest technology. Via your mobile phone you can track any changes to your flight status, gate and baggage claim details, and with Orbitz’s full-service mobile apps for iPhone and Android you can view these trip details anytime anywhere. You can also get fare alerts and travel updates to keep you informed of the cheapest flights from Boston to Windermere.

Earn Rewards on Your Boston to Windermere Flights

At Orbitz you can benefit from low cost travel and have your loyalty rewarded on certain types of Boston to Windermere flights. All you need to do is enter you frequent flyer number when booking and rack up your rewards through Orbitz online on the Traveler Information page for use on future flights. You can even add your frequent flyer number to an existing reservation to start the ball rolling.

More Destinations

More Destinations

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.