$29 Cheap flight deals from Hagerstown (DCA) 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 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.

Fri, Jan 9 - Mon, Jan 12
IAD
Washington Dulles Intl.
MCO
Orlando Intl.
$169 Roundtrip, just found
$169
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Jan 9 from Washington Dulles Intl. to Orlando Intl., returning Mon, Jan 12, priced at $169 just found
Sat, Jan 10 - Fri, Jan 23
DCA
Ronald Reagan Washington National
MCO
Orlando Intl.
$200 Roundtrip, found 16 hours ago
$200
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Sat, Jan 10 from Ronald Reagan Washington National to Orlando Intl., returning Fri, Jan 23, priced at $200 found 16 hours ago
Fri, Jan 9 - Mon, Jan 12
BWI
Baltimore Washington Intl. Thurgood Marshall
MCO
Orlando Intl.
$204 Roundtrip, just found
$204
Roundtrip
just found
Select Spirit Airlines flight, departing Fri, Jan 9 from Baltimore Washington Intl. Thurgood Marshall to Orlando Intl., returning Mon, Jan 12, priced at $204 just found

Airfares from $29 One Way, $58 Round Trip from Hagerstown to Windermere

Prices starting at $58 for return flights and $29 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.

Mon, Jan 19 - Fri, Jan 30
IAD
Washington
MCO
Orlando
$58 Roundtrip, found 5 days ago
$58
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Mon, Jan 19 from Washington to Orlando, returning Fri, Jan 30, priced at $58 found 5 days ago
Sun, Feb 1 - Wed, Feb 4
BWI
Baltimore
MCO
Orlando
$58 Roundtrip, found 1 hour ago
$58
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sun, Feb 1 from Baltimore to Orlando, returning Wed, Feb 4, priced at $58 found 1 hour ago
Tue, Feb 3 - Wed, Feb 4
BWI
Baltimore
MCO
Orlando
$63 Roundtrip, found 6 hours ago
$63
Roundtrip
found 6 hours ago
Select Spirit Airlines flight, departing Tue, Feb 3 from Baltimore to Orlando, returning Wed, Feb 4, priced at $63 found 6 hours ago
Fri, Jan 30 - Fri, Feb 13
IAD
Washington
MCO
Orlando
$80 Roundtrip, found 8 hours ago
$80
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Fri, Jan 30 from Washington to Orlando, returning Fri, Feb 13, priced at $80 found 8 hours ago
Mon, Mar 9 - Mon, Mar 16
DCA
Washington
MCO
Orlando
$105 Roundtrip, found 19 hours ago
$105
Roundtrip
found 19 hours ago
Select Southwest Airlines flight, departing Mon, Mar 9 from Washington to Orlando, returning Mon, Mar 16, priced at $105 found 19 hours ago

Windermere economy flight packages

Price found within the past 48 hours. Click for updated prices.
Seasons Florida Resort
2.0-star property

Seasons Florida Resort

8.8/10 Excellent! (3,229 reviews)

Feb 7 - Feb 14

7 night stay

Baltimore (BWI) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Price was $585, price is now $295 per person
$295
per person
found 10 hours ago
Nice room, very clean, friendly staff. They didn't have breakfast that why I'm giving 4 star

Reviewed on Jan 2, 2026

Summerville Vacation Homes by Columbia Management
4.0-star property

Summerville Vacation Homes by Columbia Management

8.4/10 Very Good! (152 reviews)

Feb 13 - Feb 18

5 night stay

Baltimore (BWI) to Orlando (MCO)

Frontier Airlines • Coach

Orlando (MCO) to Baltimore (BWI)

Spirit Airlines • Coach
Save 100% on your flight
Price was $1,208, price is now $700 per person
$700
per person
just found
This concept is nicer than staying in a hotel room. The home was spacious and decorated very well. All necessities were provided. However, the ice maker in the refrigerator was not working. We were only there for 3 nights so I didn’t bother management with it.

Reviewed on Apr 19, 2021

Westgate Town Center Resort
4.0-star property

Westgate Town Center Resort

8/10 Very Good! (1,367 reviews)

Feb 15 - Feb 20

5 night stay

Baltimore (BWI) to Orlando (MCO)

Frontier Airlines • Coach

Orlando (MCO) to Baltimore (BWI)

Spirit Airlines • Coach
Price was $873, price is now $332 per person
$332
per person
found 4 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

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

Windermere first class flight packages

Price found within the past 48 hours. Click for updated prices.
Motel 6 Lakeland, FL
2.0-star property

Motel 6 Lakeland, FL

6/10 (387 reviews)

Feb 18 - Feb 21

3 night stay

Washington (IAD) to Orlando (ORL)

United • Roundtrip • FirstClass
Price was $804, price is now $787 per person
$787
per person
found 1 hour ago
It's an above average motel 6. No complaints

Reviewed on Jul 26, 2024

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

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

The perfect trip begins with Orbitz. From booking your flights from Hagerstown to Windermere to finding the best hotels, Orbitz has got it covered.

Stress-free Searching

With an easy to use system, Orbitz takes the stress and expense out of travel. Not only does Orbitz match your Hagerstown to Windermere flights to your ideal hotel, the Display Matrix shows your deals and discounts, including free nights and other savings.

Be One Step Ahead

Need to know what is going on at the airport before you get there? With Orbitz’s free alerts service, you can quickly find out about any booking changes, or flight from Hagerstown to Windermere disruptions, saving you hours of wasted time. And if you are being picked up at the airport after your Hagerstown to Windermere flights, have alerts sent straight to your contact’s mobile phone or email.

Cutting-Edge Mobile Tools

Find the best price on flights from Hagerstown to Windermere with Orbitz’s mobile apps for iPhone and Android. Use m.orbitz.com on your mobile browser to check your gate, baggage allowance and delays, or find exclusive deals on hotels only available to mobile users.

We Work, you Rest and Play

Not only does booking with us ensure guaranteed low prices, but Orbitz does the hard work, leaving you to relax. Just tell us what you want, from Hagerstown to Windermere flights, to great deals on hotels and car rental, and activities and tours, and we will do all the rest.

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.