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Stewart

$105+ Cheap flights from Massachusetts to New Windsor (SWF)

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 10/2. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — SWF
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Massachusetts to Stewart

Keep the following information in mind while searching for Massachusetts to Stewart flight deals. Data was last updated September 15, 2025.

Round-trip from

$206
(Kiwi.com)

One-way from

$105
(Kiwi.com)

Popular in

February

Cheapest in

October

Average price

$182
From Massachusetts to New Windsor Stewart
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One-way flight from Massachusetts to New Windsor Stewart
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Highest demand for flights based on searches. 8% potential increase in price ($19 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Massachusetts to Stewart

Cheapest flights from Massachusetts to Stewart
Explore the most affordable flight options available from Massachusetts to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/308:24 pmBOS - SWF
1 stop14h 17mMultiple Airlines
Mon 11/312:01 pmSWF - BOS
1 stop23h 15mMultiple Airlines
Deal found 9/12$206
This Mytrip deal was found by Cheapflights users on 9/14. 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 10/26:49 pmBOS - SWF
1 stop16h 32mMultiple Airlines
Sun 10/55:45 pmSWF - BOS
1 stop15h 15mMultiple Airlines
Deal found 9/14$275
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/59:55 amBOS - SWF
1 stop7h 00mMultiple Airlines
Mon 10/611:01 amSWF - BOS
1 stop24h 25mMultiple Airlines
Deal found 9/14$303
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/59:55 amBOS - SWF
1 stop7h 00mMultiple Airlines
Fri 10/3111:31 amSWF - BOS
1 stop23h 45mMultiple Airlines
Deal found 9/14$312
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/210:00 amBOS - SWF
1 stop6h 55mMultiple Airlines
Fri 10/312:11 pmSWF - BOS
1 stop11h 46mMultiple Airlines
Deal found 9/14$321
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/169:55 amBOS - SWF
1 stop7h 00mMultiple Airlines
Fri 10/1711:31 amSWF - BOS
1 stop23h 55mMultiple Airlines
Deal found 9/15$331
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/308:24 pmBOS - SWF
1 stop14h 17mMultiple Airlines
Thu 11/611:43 amSWF - BOS
1 stop10h 25mMultiple Airlines
Deal found 9/15$367
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/83:56 pmBOS - SWF
1 stop20h 46mMultiple Airlines
Mon 11/1012:01 pmSWF - BOS
1 stop12h 39mMultiple Airlines
Deal found 9/15$384
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/246:57 pmBOS - SWF
2 stops40h 30mMultiple Airlines
Mon 12/15:49 pmSWF - BOS
1 stop21h 07mMultiple Airlines
Deal found 9/14$390

Cheapflights Fare Finder

 
Customize your flight search to find flights from Massachusetts to Stewart 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 September 15, 2025.
Use the filters below to find and compare flights from Massachusetts to New Windsor that are best for you.

Fly from

Massachusetts

Fly to

Stewart

Route

Depart

Return

Price

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Thu 10/30

8:24 pm-10:41 am

1 stop14h 17m

New Windsor Stewart

Mon 11/3

12:01 pm-11:16 am

1 stop23h 15m

$206

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Thu 10/2

6:49 pm-11:21 am

1 stop16h 32m

New Windsor Stewart

Sun 10/5

5:45 pm-9:00 am

1 stop15h 15m

$275

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Sun 10/5

9:55 am-4:55 pm

1 stop7h 00m

New Windsor Stewart

Mon 10/6

11:01 am-11:26 am

1 stop24h 25m

$303

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Sun 10/5

9:55 am-4:55 pm

1 stop7h 00m

New Windsor Stewart

Fri 10/31

11:31 am-11:16 am

1 stop23h 45m

$312

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Thu 10/2

10:00 am-4:55 pm

1 stop6h 55m

New Windsor Stewart

Fri 10/3

12:11 pm-11:57 pm

1 stop11h 46m

$321

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Thu 10/30

8:24 pm-10:41 am

1 stop14h 17m

New Windsor Stewart

Thu 11/6

11:43 am-10:08 pm

1 stop10h 25m

$367

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Sat 11/8

3:56 pm-12:42 pm

1 stop20h 46m

New Windsor Stewart

Mon 11/10

12:01 pm-12:40 am

1 stop12h 39m

$384

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Mon 11/24

6:57 pm-11:27 am

2 stops40h 30m

New Windsor Stewart

Mon 12/1

5:49 pm-2:56 pm

1 stop21h 07m

$390

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Thu 10/2

6:49 pm-11:21 am

1 stop16h 32m

$105

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Thu 10/16

8:24 pm-10:41 am

1 stop14h 17m

$108

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 19 results
1
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Best time to book a flight from Massachusetts to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Massachusetts 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 Massachusetts to New Windsor

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

Currently, October is the cheapest month in which you can book a flight from Massachusetts to New Windsor (average of $109). Flying from Massachusetts to New Windsor in December is currently the most expensive (average of $202). 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.

Related info for your journey

Find useful and relevant information for your journey from Massachusetts to Stewart. 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 into for flights to New Windsor from Massachusetts?

    Located just 4.3 mi from the city center, New Windsor Stewart (SWF) is the airport most travelers will use when flying to New Windsor from Massachusetts.

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

    Most travelers choose Boston Logan Intl - New Windsor Stewart, Albany Intl - New Windsor Stewart or Hartford Bradley Intl - New Windsor Stewart when deciding on the best route from Massachusetts to New Windsor.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Massachusetts to Stewart 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 Massachusetts to New Windsor?

    Currently, October is the cheapest month in which you can book a flight from Massachusetts to New Windsor (average of $109). Flying from Massachusetts to New Windsor in December is currently the most expensive (average of $202). 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.

See more FAQs

Traveling to a place near New Windsor?

Book flights to New Windsor if you plan to visit one of these locations
Kingston

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