In terms of precipitation, rainfall in Maryland ranges from 2.9 - 4.1 inches per month. July is typically the wettest month, when rainfall can reach 4.1 in. February is typically the driest time to visit Maryland when rainfall is around 2.9 in.

If weather is an important factor for your trip to Maryland, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 77.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 33.8 F).

What are the most popular routes from New Windsor to Maryland?

Most travelers choose New Windsor Stewart - Philadelphia, New Windsor Stewart - Baltimore/Washington or New Windsor Stewart - Washington, D.C. Dulles Intl when deciding on the best route from New Windsor to Maryland.

What is the cheapest time of day to fly from SWF to MD?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from New Windsor to Maryland as you normally would.

What airport do you fly from for flights from New Windsor to Maryland?

New Windsor Stewart (SWF), located 4.3 mi from the city center, is the airport you fly out of when you book flights from New Windsor to Maryland.

Can I find deals for flights from Stewart to Maryland that include hotel bookings?

Yes. In addition to deals on Stewart to Maryland flights, Cheapflights offers vacation packages that include both flights and hotel.

How can I find direct flights from Stewart to Maryland?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Stewart to Maryland.

Can I find deals for business class flights from Stewart to Maryland?

Yes. Cheapflights offers flight deals from Stewart to Maryland by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$242+ Cheap Flights from New Windsor to Maryland

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Cheap flight deals from Stewart to Maryland

One-way

One-way flights from Stewart to Maryland
Search for one-way flight options from Stewart to Maryland. Find affordable one-way fares based on user searches. Data last updated September 28, 2026.

Sun 10/115:48 pm -

1 stop26h 23m

Wed 12/3112:00 am -

Nonstop0h 00m

Deal found 9/23

$242

Fri 11/612:16 pm -

3 stops31h 20m

Wed 12/3112:00 am -

Nonstop0h 00m

Deal found 9/26

$331

Find flight deals from Stewart to Maryland

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Highest demand for flights based on searches. 9% potential increase in price ($24 potential increase over avg. RT price).

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Average for round-trip flights in September 2026

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New WindsorHagerstown

SWF New Windsor Stewart - HGR Hagerstown Regional

SWFHGR

New Windsor Stewart

Sun 10/11

5:48 pm-8:11 pm

1 stop26h 23m

Hagerstown Regional

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$242

New WindsorSalisbury

SWF New Windsor Stewart - SBY Salisbury-Ocean City

SWFSBY

New Windsor Stewart

Fri 11/6

12:16 pm-7:36 pm

3 stops31h 20m

Salisbury-Ocean City

Wed 12/31

12:00 am-12:00 am

Nonstop0h 00m

$331

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/23

Sorted by cheapest first

Best time to book a flight from Stewart to Maryland

Have a flexible travel schedule? Discover the best time to fly to Maryland from Stewart with our price prediction graph.

SWF-HGR

SWF-SBY

Estimated round-trip price

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Everything you need to know about your flight from New Windsor to Maryland

SWF-USMD

SWF-HGR

SWF-SBY

No data available for this route at this time. Please check back soon.

Related info for your journey

What airport do you fly from for flights from New Windsor to Maryland?
New Windsor Stewart (SWF), located 4.3 mi from the city center, is the airport you fly out of when you book flights from New Windsor to Maryland.
What are the most popular routes from New Windsor to Maryland?
Most travelers choose New Windsor Stewart - Philadelphia, New Windsor Stewart - Baltimore/Washington or New Windsor Stewart - Washington, D.C. Dulles Intl when deciding on the best route from New Windsor to Maryland.
Can I find deals for flights from Stewart to Maryland that include hotel bookings?
Yes. In addition to deals on Stewart to Maryland flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Stewart to Maryland?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Stewart to Maryland.
Can I find deals for business class flights from Stewart to Maryland?
Yes. Cheapflights offers flight deals from Stewart to Maryland by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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$242+ Cheap flights from New Windsor (SWF) to Maryland

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/11. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Stewart to Maryland with Cheapflights

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Cheap flight deals from Stewart to Maryland

One-way flights from Stewart to MarylandSearch for one-way flight options from Stewart to Maryland. Find affordable one-way fares based on user searches. Data last updated September 28, 2026.

Search for one-way flight options from Stewart to Maryland. Find affordable one-way fares based on user searches. Data last updated September 28, 2026.

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Use the filters below to find and compare flights from New Windsor to Maryland that are best for you.

Best time to book a flight from Stewart to Maryland

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Cheapflights Insights

Related info for your journey

What airport do you fly from for flights from New Windsor to Maryland?

What are the most popular routes from New Windsor to Maryland?

Can I find deals for flights from Stewart to Maryland that include hotel bookings?

How can I find direct flights from Stewart to Maryland?

Can I find deals for business class flights from Stewart to Maryland?

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Stewart to Maryland

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Complete your trip

Complete your trip to Maryland by adding a car rental and/or hotel reservation to your travel itinerary.

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Stewart and Maryland flights

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One-way flights from Stewart to Maryland
Search for one-way flight options from Stewart to Maryland. Find affordable one-way fares based on user searches. Data last updated September 28, 2026.