$27 Cheap flight deals from Hagerstown (DCA) to Windermere (ORL)

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This Weekend's Flight Deals from Hagerstown 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, May 10 - Sat, May 17
BWI
Baltimore Washington Intl. Thurgood Marshall
MCO
Orlando Intl.
$173 Roundtrip, just found
$173
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, May 10 from Baltimore Washington Intl. Thurgood Marshall to Orlando Intl., returning Sat, May 17, priced at $173 just found
Sat, May 10 - Tue, May 13
DCA
Ronald Reagan Washington National
MCO
Orlando Intl.
$234 Roundtrip, just found
$234
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, May 10 from Ronald Reagan Washington National to Orlando Intl., returning Tue, May 13, priced at $234 just found
Sun, May 11 - Sat, May 17
IAD
Washington Dulles Intl.
MCO
Orlando Intl.
$236 Roundtrip, found 1 hour ago
$236
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sun, May 11 from Washington Dulles Intl. to Orlando Intl., returning Sat, May 17, priced at $236 found 1 hour ago

Airfares from $27 One Way, $53 Round Trip from Hagerstown to Windermere

Prices starting at $53 for return flights and $27 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, May 28 - Tue, Jun 3
BWI
Baltimore
MCO
Orlando
$53 Roundtrip, just found
$53
Roundtrip
just found
Select Spirit Airlines flight, departing Wed, May 28 from Baltimore to Orlando, returning Tue, Jun 3, priced at $53 just found
Thu, May 29 - Mon, Jun 2
BWI
Baltimore
MCO
Orlando
$54 Roundtrip, found 3 hours ago
$54
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Thu, May 29 from Baltimore to Orlando, returning Mon, Jun 2, priced at $54 found 3 hours ago
Tue, May 27 - Sat, May 31
BWI
Baltimore
MCO
Orlando
$60 Roundtrip, just found
$60
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, May 27 from Baltimore to Orlando, returning Sat, May 31, priced at $60 just found
Sat, May 31 - Sat, Jun 7
IAD
Washington
MCO
Orlando
$75 Roundtrip, just found
$75
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, May 31 from Washington to Orlando, returning Sat, Jun 7, priced at $75 just found
Tue, Jul 8 - Sat, Jul 12
IAD
Washington
MCO
Orlando
$125 Roundtrip, found 5 hours ago
$125
Roundtrip
found 5 hours ago
Select United flight, departing Tue, Jul 8 from Washington to Orlando, returning Sat, Jul 12, priced at $125 found 5 hours ago

Windermere economy flight packages

Price found within the past 48 hours. Click for updated prices.
Westgate Blue Tree Resort in Lake Buena Vista
3.5-star property

Westgate Blue Tree Resort in Lake Buena Vista

8.4/10 Very Good! (949 reviews)

Jun 10 - Jun 14

4 night stay

Baltimore (BWI) to Orlando (MCO)

Spirit Airlines • Roundtrip • Coach
per person
found 6 hours ago
Our 8 day stay was wonderful. This is our preferred WG property in the Orlando area because it is less crowded and parking is readily available. The full kitchen and washer/dryer in room made this ideal for us. There are plenty of grilling areas and numerous pools throughout the property.

Reviewed on Jul 3, 2024

Westgate Lakes Resort & Spa Universal Studios Area
4.0-star property

Westgate Lakes Resort & Spa Universal Studios Area

8/10 Very Good! (4,595 reviews)

Jun 12 - Jun 15

3 night stay

Baltimore (BWI) to Orlando (MCO)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Check-in took over 35 min. We were put at the very last building on the main floor by the elevator. It was noisy all night and when staff started their shift in the morning. You can hear everything going on outside of the window

Reviewed on May 5, 2025

Seasons Florida Resort
2.0-star property

Seasons Florida Resort

8.8/10 Excellent! (2,698 reviews)

Jun 23 - Jun 28

5 night stay

Baltimore (BWI) to Orlando (MCO)

Spirit Airlines • Coach

Orlando (MCO) to Baltimore (BWI)

Frontier Airlines • Coach
Save 100% on your flight
per person
found 18 hours ago
Probably the best hotel for this price range. I didn’t have high expectation when booking, but the cleanliness and property condition is way above my expectation. I like how they make the window tinted for one way view so during the day you can open the blinds without worrying that people can see inside the room from outside.

Reviewed on Apr 9, 2025

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Windermere first class 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

7.8/10 Good! (1,199 reviews)

Jun 27 - Jun 30

3 night stay

Washington (WAS) to Orlando (MCO)

Delta • Non-stop roundtrip • FirstClass
per person
found 8 hours 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

Margaritaville Cottages Orlando with H2O Waterpark by Vstays
4.0-star property

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

9/10 Wonderful! (1,002 reviews)

Jun 27 - Jun 30

3 night stay

Washington (WAS) to Orlando (MCO)

Delta • Non-stop roundtrip • FirstClass
per person
found 8 hours 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

Kompose Boutique Resort at Theme Parks
4.0-star property

Kompose Boutique Resort at Theme Parks

No reviews

Jun 27 - Jun 30

3 night stay

Washington (WAS) to Orlando (MCO)

Delta • Non-stop roundtrip • FirstClass
per person
found 8 hours ago
Beautifully designed facility. The staff are excellent and friendly.

Reviewed on May 3, 2025

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More About Flying To Windermere from Hagerstown

Route Information for Flights from Hagerstown to Windermere

Origin Airport IATA Code
DCA
Destination Airport IATA Code
ORL
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Hagerstown to Windermere

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Get a great package with your Hagerstown to Windermere flights

With frequent updates on your flight status, including delays and changes in bookings, traveling becomes more hassle-free than ever. Not only do we offer huge discounted deals on flights from Hagerstown to Windermere, we also have fantastic savings on vacation packages, hotel room, cruises, activities, and car rentals so you can pick and choose and create the best travel package for you.

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.