$52 Cheap flight deals from Hagerstown (DCA) to Winter Park (ORL)

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This Weekend's Flight Deals from Hagerstown to Winter Park

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, Aug 1 - Sat, Aug 8
HGR
Hagerstown Regional
SFB
Orlando Sanford Intl.
$203 Roundtrip, found 5 days ago
$203
Roundtrip
found 5 days ago
Select Allegiant Air flight, departing Sat, Aug 1 from Hagerstown Regional to Orlando Sanford Intl., returning Sat, Aug 8, priced at $203 found 5 days ago
Sun, Aug 2 - Fri, Aug 7
IAD
Washington Dulles Intl.
MCO
Orlando Intl.
$313 Roundtrip, just found
$313
Roundtrip
just found
Select Frontier Airlines flight, departing Sun, Aug 2 from Washington Dulles Intl. to Orlando Intl., returning Fri, Aug 7, priced at $313 just found
Fri, Jul 31 - Sun, Aug 2
BWI
Baltimore Washington Intl. Thurgood Marshall
MCO
Orlando Intl.
$341 Roundtrip, just found
$341
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Jul 31 from Baltimore Washington Intl. Thurgood Marshall to Orlando Intl., returning Sun, Aug 2, priced at $341 just found
Sun, Aug 2 - Wed, Aug 5
DCA
Ronald Reagan Washington National
MCO
Orlando Intl.
$418 Roundtrip, found 1 hour ago
$418
Roundtrip
found 1 hour ago
Select Southwest Airlines flight, departing Sun, Aug 2 from Ronald Reagan Washington National to Orlando Intl., returning Wed, Aug 5, priced at $418 found 1 hour ago

Airfares from $52 One Way, $101 Round Trip from Hagerstown to Winter Park

Prices starting at $101 for return flights and $52 for one-way flights to Winter Park 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, Oct 26 - Wed, Nov 4
HGR
Hagerstown
SFB
Orlando
$101 Roundtrip, found 2 hours ago
$101
Roundtrip
found 2 hours ago
Select Allegiant Air flight, departing Mon, Oct 26 from Hagerstown to Orlando, returning Wed, Nov 4, priced at $101 found 2 hours ago
Tue, Sep 15 - Wed, Sep 16
IAD
Washington
MCO
Orlando
$104 Roundtrip, found 4 hours ago
$104
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Tue, Sep 15 from Washington to Orlando, returning Wed, Sep 16, priced at $104 found 4 hours ago
Tue, Sep 15 - Wed, Sep 16
BWI
Baltimore
MCO
Orlando
$104 Roundtrip, found 4 hours ago
$104
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Tue, Sep 15 from Baltimore to Orlando, returning Wed, Sep 16, priced at $104 found 4 hours ago
Mon, Aug 24 - Mon, Aug 31
IAD
Washington
MCO
Orlando
$116 Roundtrip, found 10 hours ago
$116
Roundtrip
found 10 hours ago
Select Breeze Airways flight, departing Mon, Aug 24 from Washington to Orlando, returning Mon, Aug 31, priced at $116 found 10 hours ago
Wed, Sep 23 - Sat, Sep 26
DCA
Washington
MCO
Orlando
$199 Roundtrip, found 3 hours ago
$199
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Wed, Sep 23 from Washington to Orlando, returning Sat, Sep 26, priced at $199 found 3 hours ago

Winter Park economy flight packages

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

Seasons Florida Resort

9/10 Wonderful! (3,728 reviews)

Sep 18 - Sep 21

3 night stay

Baltimore (BWI) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Price was $363, price is now $223 per person
$223
per person
found 1 day ago

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

Westgate Palace Hotel / Universal / I-Drive

9/10 Wonderful! (1,294 reviews)

Sep 6 - Sep 8

2 night stay

Baltimore (BWI) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $476, price is now $265 per person
$265
per person
found 1 day ago
Nice roomy and clean

Reviewed on Jul 28, 2026

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

Westgate Lakes Resort & Spa Universal Studios Area

8.4/10 Very Good! (6,738 reviews)

Sep 4 - Sep 7

3 night stay

Baltimore (BWI) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $603, price is now $364 per person
$364
per person
found 1 day ago
Our first night after checking in at almost 1am our room had no working AC. We were miserable. Told it would be cooled off in one hour, and they never happened. They were able to move our room the next day. Difficult to find ice while we waited for our ice maker to start making ice. Washer and dryer are extremely loud. The shops and restaurant on site were awesome!! Close to a Walmart if you’re staying in a room with a kitchen.

Reviewed on Jul 28, 2026

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Winter Park packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
The Delaney Hotel
3.5-star property

The Delaney Hotel

9.6/10 Exceptional! (1,157 reviews)

Sep 6 - Sep 8

2 night stay

Baltimore (BWI) to Orlando (MCO)

Frontier Airlines • Roundtrip • PremiumEconomy
Price was $490, price is now $398 per person
$398
per person
found 3 hours ago
We booked because it was close to the hospital the night prior to my husband’s surgery. Was pleasantly surprised at how nice it is. Impressed by a comfortable bed & pillows and they even have umbrellas in the room for guest use.

Reviewed on Jul 28, 2026

Florida Hotel & Conference Center in the Florida Mall
3.5-star property

Florida Hotel & Conference Center in the Florida Mall

9.2/10 Wonderful! (1,380 reviews)

Sep 5 - Sep 8

3 night stay

Washington (WAS) to Orlando (MCO)

Frontier Airlines • Roundtrip • PremiumEconomy
Price was $739, price is now $504 per person
$504
per person
found 21 hours ago

The Grove Resort & Water Park Orlando
4.0-star property

The Grove Resort & Water Park Orlando

8/10 Very Good! (10,481 reviews)

Sep 5 - Sep 8

3 night stay

Washington (WAS) to Orlando (MCO)

Frontier Airlines • Roundtrip • PremiumEconomy
Price was $655, price is now $558 per person
$558
per person
found 21 hours ago
This is my second time staying at the Grove ! The property is beautiful and the amenities are enough by itself to keep the kids entertained for the entire vacation . This time my experience was a bit different. I was a bit disappointed that my 3 bedroom condo was very short on bath towels. Each bathroom came with only 1 face towel. Also we bought groceries to cook breakfast by there was only 1 small boiling pot. That was an inconvenience that caused me to lose money. The Grove is still my first choice when visiting Orlando.

Reviewed on Jul 28, 2026

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Winter Park first class flight packages

Price found within the past 48 hours. Click for updated prices.
The Delaney Hotel
3.5-star property

The Delaney Hotel

9.6/10 Exceptional! (1,157 reviews)

Sep 11 - Sep 13

2 night stay

Washington (DCA) to Orlando (MCO)

American Airlines • Non-stop • FirstClass

Orlando (MCO) to Washington (DCA)

Frontier Airlines • Non-stop • FirstClass
Price was $978, price is now $857 per person
$857
per person
found 1 day ago
We booked because it was close to the hospital the night prior to my husband’s surgery. Was pleasantly surprised at how nice it is. Impressed by a comfortable bed & pillows and they even have umbrellas in the room for guest use.

Reviewed on Jul 28, 2026

Florida Hotel & Conference Center in the Florida Mall
3.5-star property

Florida Hotel & Conference Center in the Florida Mall

9.2/10 Wonderful! (1,380 reviews)

Sep 11 - Sep 13

2 night stay

Washington (DCA) to Orlando (MCO)

American Airlines • Non-stop • FirstClass

Orlando (MCO) to Washington (DCA)

Frontier Airlines • Non-stop • FirstClass
Price was $1,022, price is now $874 per person
$874
per person
found 1 day ago

Villatel Resort Orlando
4.0-star property

Villatel Resort Orlando

9.4/10 Exceptional! (499 reviews)

Sep 11 - Sep 13

2 night stay

Washington (DCA) to Orlando (MCO)

American Airlines • Non-stop • FirstClass

Orlando (MCO) to Washington (DCA)

Frontier Airlines • Non-stop • FirstClass
Price was $1,375, price is now $1,241 per person
$1,241
per person
found 1 day ago
Came for my daughter’s birthday that was turning 6. A big party of nine stayed at one of the homes. We had an amazing time it’s so much to do. Will definitely be booking again.

Reviewed on Jul 27, 2026

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More About Flying To Winter Park from Hagerstown

Route Information for Flights from Hagerstown to Winter Park

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

Hagerstown to Winter Park

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With the best deals and easy searching options, Orbitz make it easy and fun to find cheap Hagerstown to Winter Park flights, a great hotel, or a full vacation package. With Orbitz’s low price guarantee, you always get great discounts on air ticket prices.

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.