$45 Cheap flight deals from Boston (BOS) to Leesburg (ORL)
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This Weekend's Flight Deals from Boston to Leesburg
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.
BOS
Logan Intl.
MCO
Orlando Intl.
$139 Roundtrip, found 3 hours ago
$139
Roundtrip
found 3 hours ago
PSM
Portsmouth Intl.
MCO
Orlando Intl.
$172 Roundtrip, found 1 day ago
$172
Roundtrip
found 1 day ago
MHT
Manchester-Boston Regional
MCO
Orlando Intl.
$268 Roundtrip, found 1 day ago
$268
Roundtrip
found 1 day ago
PVD
T.F. Green
MCO
Orlando Intl.
$295 Roundtrip, just found
$295
Roundtrip
just found
Airfares from $45 One Way, $108 Round Trip from Boston to Leesburg
Prices starting at $108 for return flights and $45 for one-way flights to Leesburg were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
BOS
Boston
MCO
Orlando
$108 Roundtrip, just found
$108
Roundtrip
just found
PSM
Portsmouth
MCO
Orlando
$112 Roundtrip, found 3 hours ago
$112
Roundtrip
found 3 hours ago
MHT
Manchester
MCO
Orlando
$132 Roundtrip, found 2 days ago
$132
Roundtrip
found 2 days ago
PVD
Providence
MCO
Orlando
$146 Roundtrip, found 1 day ago
$146
Roundtrip
found 1 day ago
PVD
Providence
MCO
Orlando
$195 Roundtrip, found 5 days ago
$195
Roundtrip
found 5 days ago
Leesburg economy flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Westgate Lakes Resort & Spa Universal Studios Area
8.4/10 Very Good! (5,960 reviews)
May 8 - May 11
3 night stay
Boston (BOS) to Orlando (MCO)
Frontier Airlines • Coach
Orlando (MCO) to Boston (BOS)
Southwest Airlines • Coach
Save 100% on your flight
Price was $858, price is now $369 per person
$369
per person
found 1 day ago
We had to get 4 room keys for our door to finally work, however staff was kind and helped us as much as they could.
Reviewed on Feb 12, 2026
3.0-star property
Palazzo Lakeside Hotel
8.2/10 Very Good! (5,182 reviews)
May 8 - May 11
3 night stay
Boston (BOS) to Orlando (MCO)
Delta • Coach
Orlando (MCO) to Boston (BOS)
Southwest Airlines • Coach
Price was $1,154, price is now $400 per person
$400
per person
found 1 day ago
Gracias excelentes 👌 pronto estare de vuelta bendiciones
Reviewed on Feb 9, 2026
4.0-star property
Westgate Cocoa Beach Resort
8.6/10 Excellent! (525 reviews)
May 1 - May 5
4 night stay
Boston (BOS) to Orlando (MCO)
Frontier Airlines • Roundtrip • Coach
Price was $1,540, price is now $798 per person
$798
per person
found 1 day 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
Leesburg packages with premium economy flights
Price found within the past 48 hours. Click for updated prices.
3.5-star property
Florida Hotel & Conference Center in the Florida Mall
9.2/10 Wonderful! (2,530 reviews)
May 22 - May 26
4 night stay
Boston (BOS) to Orlando (MCO)
Delta • PremiumEconomy
Orlando (MCO) to Boston (BOS)
Spirit Airlines • PremiumEconomy
Price was $1,074, price is now $860 per person
$860
per person
found 1 day ago
What a stunning and beautiful hotel. My son loved it also and having full access to the mall was a bonus!! Will definitely be back soon!
Reviewed on Dec 9, 2025
4.0-star property
Margaritaville Cottages Orlando by Vstays with H2O Waterpark
9.2/10 Wonderful! (1,008 reviews)
May 22 - May 26
4 night stay
Boston (BOS) to Orlando (MCO)
Delta • PremiumEconomy
Orlando (MCO) to Boston (BOS)
Spirit Airlines • PremiumEconomy
Price was $1,572, price is now $1,165 per person
$1,165
per person
found 1 day ago
We were very displeased with the cleanliness of our cottage upon arrival. I found multiple hairs on the ground and furniture, so vacuumed Before I even unpacked my suitcase. At the end of the night, our feet were so filthy dirty, we had to wash them before we could get into bed because the floors werent clean. The pool was gross, even had a used band aid in it. The kitchen barely had enough dishes and they left nothing to help with cooking coffee or anything. We've had many vrbo properties in the past, and this was one of the least desirable that we've stayed at.
Reviewed on Oct 7, 2024
3.5-star property
The Delaney Hotel
9.6/10 Exceptional! (1,068 reviews)
May 22 - May 26
4 night stay
Boston (BOS) to Orlando (MCO)
Delta • PremiumEconomy
Orlando (MCO) to Boston (BOS)
Spirit Airlines • PremiumEconomy
Price was $1,073, price is now $865 per person
$865
per person
found 1 day ago
Great location for hospital access
Reviewed on Jul 8, 2025
Leesburg first class flight packages
Price found within the past 48 hours. Click for updated prices.
2.0-star property
Seasons Florida Resort
9/10 Wonderful! (3,493 reviews)
May 19 - May 23
4 night stay
Boston (BOS) to Orlando (MCO)
Delta • Roundtrip • FirstClass
Price was $981, price is now $822 per person
$822
per person
found 1 day ago
I rated 5-stars for the location and price of the stay. The rooms were in fact clean, but perhaps the age of the hotel (even though renovated) had a particular smell that only helped when running the a/c which wasn’t needed (I visited during the January attic blast).
Reviewed on Feb 10, 2026
4.0-star property
Margaritaville Cottages Orlando by Vstays with H2O Waterpark
9.2/10 Wonderful! (1,008 reviews)
May 19 - May 23
4 night stay
Boston (BOS) to Orlando (MCO)
Delta • Roundtrip • FirstClass
Price was $1,709, price is now $1,279 per person
$1,279
per person
found 1 day ago
We were very displeased with the cleanliness of our cottage upon arrival. I found multiple hairs on the ground and furniture, so vacuumed Before I even unpacked my suitcase. At the end of the night, our feet were so filthy dirty, we had to wash them before we could get into bed because the floors werent clean. The pool was gross, even had a used band aid in it. The kitchen barely had enough dishes and they left nothing to help with cooking coffee or anything. We've had many vrbo properties in the past, and this was one of the least desirable that we've stayed at.
Reviewed on Oct 7, 2024
4.0-star property
Westgate Town Center Resort
8/10 Very Good! (1,510 reviews)
May 19 - May 23
4 night stay
Boston (BOS) to Orlando (MCO)
Delta • Roundtrip • FirstClass
Price was $1,116, price is now $852 per person
$852
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
More About Flying To Leesburg from Boston
Route Information for Flights from Boston to Leesburg
Origin Airport IATA Code | BOS |
|---|---|
Destination Airport IATA Code | ORL |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Boston to Leesburg
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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.