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$94+ Cheap flights from New Windsor (SWF) to Massachusetts

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/30. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — BOS
May 5 — May 121
Mon 5/5
Mon 5/12
1 adult, Economy
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Cheap flight deals from Stewart to Massachusetts

Keep the following information in mind while searching for Stewart to Massachusetts flight deals. Data was last updated April 30, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$193
(Mytrip)

One-way from

$94
(Booking.com)

Popular in

April

Cheapest in

August

Average price

$279
Provider with most accurate pricing for New York (NYC)-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for New York (NYC)-Boston Logan Intl flights.
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From New Windsor Stewart to Massachusetts
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One-way flight from New Windsor Stewart to Massachusetts
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Highest demand for flights based on searches. 17% potential increase in price ($41 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Find flight deals from Stewart to Massachusetts

Cheapest flights from Stewart to Massachusetts
Explore the most affordable flight options available from Stewart to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 30, 2025.

This Mytrip deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/67:18 pmSWF - BOS
1 stop20h 26mMultiple Airlines
Sun 6/83:49 pmBOS - SWF
1 stop26h 39mMultiple Airlines
Deal found 4/29$222
This Mytrip deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/296:06 pmSWF - BDL
1 stop13h 33mMultiple Airlines
Thu 6/512:27 pmBDL - SWF
1 stop30h 01mMultiple Airlines
Deal found 4/29$289
This Mytrip deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/146:42 pmSWF - ALB
1 stop14h 35mAllegiant Air
Sun 5/187:24 pmALB - SWF
1 stop18h 31mAllegiant Air
Deal found 4/29$308
This Mytrip deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/146:42 pmSWF - ALB
1 stop14h 35mMultiple Airlines
Sun 5/182:24 pmALB - SWF
3 stops20h 41mMultiple Airlines
Deal found 4/29$352

Cheapflights Fare Finder

Customize your flight search to find flights from Stewart to Massachusetts that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 30, 2025.
Use the filters below to find and compare flights from New Windsor to Massachusetts that are best for you.

Fly from

Stewart

Fly to

Massachusetts

Route

Depart

Return

Price

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 6/6

7:18 pm-3:44 pm

1 stop20h 26m

Boston Logan Intl

Sun 6/8

3:49 pm-6:28 pm

1 stop26h 39m

$222

New WindsorHartford

SWF - BDL

SWFBDL

New Windsor Stewart

Thu 5/29

6:06 pm-7:39 am

1 stop13h 33m

Hartford Bradley Intl

Thu 6/5

12:27 pm-6:28 pm

1 stop30h 01m

$289

New WindsorAlbany

SWF - ALB

SWFALB

New Windsor Stewart

Wed 5/14

6:42 pm-9:17 am

1 stop14h 35m

Albany Intl

Sun 5/18

7:24 pm-1:55 pm

1 stop18h 31m

$308

New WindsorAlbany

SWF - ALB

SWFALB

New Windsor Stewart

Wed 5/14

6:42 pm-9:17 am

1 stop14h 35m

Albany Intl

Sun 5/18

2:24 pm-11:05 am

3 stops20h 41m

$352

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Mon 5/19

11:55 am-2:44 pm

1 stop26h 49m

$129

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 5/16

11:55 am-10:10 am

2 stops22h 15m

$164

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

Best time to book a flight from Stewart to Massachusetts

Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Stewart with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

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

What is the cheapest month to book a flight from New Windsor to Massachusetts?

Currently, January is the cheapest month in which you can book a flight from New Windsor to Massachusetts (average of $218). Flying from New Windsor to Massachusetts in July is currently the most expensive (average of $311). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Rainfall in Massachusetts by month

Plan your trip to Massachusetts by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Massachusetts ranges from 3.1 - 4.0 inches per month. March is typically the wettest month, when rainfall can reach 4.0 in. July is typically the driest time to visit Massachusetts when rainfall is around 3.1 in.

Temperature in Massachusetts by month

Plan your trip to Massachusetts by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Massachusetts, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 30.2 F).

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Massachusetts. Reviews last updated April 30, 2025.
Allegiant Air
7.3
Good
734 reviews

Overall

7.3

Crew

8.1

Food

5.9

Boarding

7.6

Comfort

6.8

Entertainment

5.5

Reviews

1 / 20
10.0
Excellent

Joellen,Aug 2024

LAS - GEG

Boarding was a hassle. I’ve had the same guy before. Never enjoy seeing him.
Allegiant Air
7.3
Good
734 reviews
Allegiant Air
7.3
Good
734 reviews

Overall

7.3

Crew

8.1

Food

5.9

Boarding

7.6

Comfort

6.8

Entertainment

5.5

Reviews

1 / 20
10.0
Excellent

Joellen,Aug 2024

LAS - GEG

Boarding was a hassle. I’ve had the same guy before. Never enjoy seeing him.

Related info for your journey

Find useful and relevant information for your journey from Stewart to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    If you book a flight to Massachusetts from New Windsor, you will be flying from Stewart, which is the city’s only airport. New Windsor Stewart (SWF) is located 4.3 mi from the center of New Windsor.

  • What are the most popular routes from New Windsor to Massachusetts?

    The most popular flight routes from New Windsor to Massachusetts are New Windsor Stewart - Boston Logan Intl, New Windsor Stewart - Hartford Bradley Intl and New Windsor Stewart - Albany Intl.

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

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

  • How can I find direct flights from Stewart to Massachusetts?

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

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

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

  • What is the cheapest month to book a flight from New Windsor to Massachusetts?

    Currently, January is the cheapest month in which you can book a flight from New Windsor to Massachusetts (average of $218). Flying from New Windsor to Massachusetts in July is currently the most expensive (average of $311). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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