Latest deals
Insights
FAQs
Price Alerts

Cheap flights from New Windsor to Massachusetts from $102

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from New Windsor to Massachusetts departing on 1/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from New Windsor to Massachusetts

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
12:13 pm - 11:19 pm
SWF
-
BOS
11h 06m1 stop
Multiple Airlines Logo
5:27 pm - 10:19 am
BOS
-
SWF
16h 52m1 stop
$368Multiple Airlines
Sun, Jan 11 - Sun, Jan 18
Multiple Airlines Logo
12:13 pm - 11:19 pm
SWF
-
BOS
11h 06m1 stop
Multiple Airlines Logo
5:27 pm - 10:19 am
BOS
-
SWF
16h 52m1 stop
$372Multiple Airlines
Sun, Jan 11 - Sun, Jan 18
Multiple Airlines Logo
12:24 pm - 12:13 pm
SWF
-
BDL
23h 49m1 stop
Multiple Airlines Logo
8:05 am - 5:56 pm
BDL
-
SWF
9h 51m1 stop
$592Multiple Airlines
Mon, Dec 29 - Fri, Jan 2
Multiple Airlines Logo
12:24 pm - 11:54 am
SWF
-
BDL
23h 30m2 stops
Multiple Airlines Logo
8:05 am - 5:56 pm
BDL
-
SWF
9h 51m1 stop
$608Multiple Airlines
Mon, Dec 29 - Fri, Jan 2
Multiple Airlines Logo
10:28 am - 11:59 pm
SWF
-
BOS
13h 31m1 stop
Multiple Airlines Logo
11:32 am - 5:55 pm
BOS
-
SWF
30h 23m2 stops
$676Multiple Airlines
Sun, Jun 14 - Fri, Jun 26
Allegiant Air Logo
10:40 am - 3:02 pm
SWF
-
ALB
28h 22m1 stop
Allegiant Air Logo
11:42 am - 9:30 am
ALB
-
SWF
21h 48m1 stop
$732Allegiant Air
Wed, Dec 31 - Sun, Jan 4
Multiple Airlines Logo
10:40 am - 3:02 pm
SWF
-
ALB
28h 22m1 stop
Multiple Airlines Logo
1:20 pm - 10:47 am
ALB
-
SWF
21h 27m2 stops
$771Multiple Airlines
Wed, Dec 31 - Sun, Jan 4

momondo Fare Finder

 
Customize your flight search to find flights from New Windsor 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, momondo users made 832,500 searches. Data last updated December 16, 2025.
Use the filters below to find and compare flights from New Windsor to Massachusetts that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Sun 1/11

12:13 pm-11:19 pm

1 stop11h 06m

Boston Logan Intl

Sun 1/18

5:27 pm-10:19 am

1 stop16h 52m

$368

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Sun 1/11

12:13 pm-11:19 pm

1 stop11h 06m

Boston Logan Intl

Sun 1/18

5:27 pm-10:19 am

1 stop16h 52m

$372

New WindsorHartford

SWF - BDL

SWFBDL

New Windsor Stewart

Mon 12/29

12:24 pm-12:13 pm

1 stop23h 49m

Hartford Bradley Intl

Fri 1/2

8:05 am-5:56 pm

1 stop9h 51m

$592

New WindsorHartford

SWF - BDL

SWFBDL

New Windsor Stewart

Mon 12/29

12:24 pm-11:54 am

2 stops23h 30m

Hartford Bradley Intl

Fri 1/2

8:05 am-5:56 pm

1 stop9h 51m

$608

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Sun 6/14

10:28 am-11:59 pm

1 stop13h 31m

Boston Logan Intl

Fri 6/26

11:32 am-5:55 pm

2 stops30h 23m

$676

New WindsorAlbany

SWF - ALB

SWFALB

New Windsor Stewart

Wed 12/31

10:40 am-3:02 pm

1 stop28h 22m

Albany Intl

Sun 1/4

11:42 am-9:30 am

1 stop21h 48m

$732

New WindsorAlbany

SWF - ALB

SWFALB

New Windsor Stewart

Wed 12/31

10:40 am-3:02 pm

1 stop28h 22m

Albany Intl

Sun 1/4

1:20 pm-10:47 am

2 stops21h 27m

$771

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Mon 1/12

11:09 am-11:57 pm

1 stop12h 48m

$102

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 1/23

11:09 am-11:57 pm

1 stop12h 48m

$110

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Sun 2/15

6:02 pm-9:08 am

1 stop15h 06m

$162

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 17 resultsSorted by cheapest first
1
2

See travel insights to Massachusetts from

How to get the cheapest flight ticket from New Windsor to Massachusetts

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from New Windsor Stewart to Massachusetts?

Allegiant Air is the most popular carrier operating from New Windsor Stewart to Massachusetts

What airlines fly to Massachusetts?

United Airlines, Delta and JetBlue are the top three most popular airlines that fly to Massachusetts from New Windsor according to our data. United Airlines is the first choice among our users, with 35% of people opting to fly with this airline when traveling to Massachusetts. Keep in mind that there are 7 different airlines that fly to Massachusetts on a routine basis, so you have a few additional options to choose from.

Cheap New Windsor to Massachusetts flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from New Windsor to Massachusetts

Fastest flight time

11h 06m

Direct flights

None
The fastest flight from New Windsor to Massachusetts takes 11h 06m
There are no direct flights from New Windsor to Massachusetts. There are no popular flight routes from New Windsor to Massachusetts.
Search flight deals

  • When did momondo last update prices for flights from New Windsor Stewart Airport to Massachusetts?

    Prices for flights from New Windsor Stewart Airport to Massachusetts were last updated today.

  • How old do you have to be to fly from New Windsor Stewart Airport to Massachusetts?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from New Windsor Stewart Airport to Massachusetts.

  • What documentation or ID do you need to fly to Massachusetts?

    The required travel and health documents for your Massachusetts trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Massachusetts. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Why use momondo?

Why should I use momondo to find a flight deal from New Windsor to Massachusetts?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from New Windsor to Massachusetts. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from New Windsor to Massachusetts with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for New Windsor to Massachusetts flights to just show those with flexible booking policies.

How can momondo help me find flights from New Windsor to Massachusetts?

Once you have performed a search for New Windsor to Massachusetts flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from New Windsor to Massachusetts right now. Can momondo alert me if prices change?

Price alerts on flights to Massachusetts from New Windsor are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Massachusetts trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Thu 1/15
Thu 1/22
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Massachusetts

Popular cities in Massachusetts

Popular flights according to clicks in the last 7 days on momondo
Flights to New Yorkfrom $45
Flights to Los Angelesfrom $48
Flights to Miamifrom $49
Flights to Chicagofrom $58
Flights to Orlandofrom $40
Flights to San Franciscofrom $58
Flights to Las Vegasfrom $49
Flights to Washington, D.C.from $57
Flights to Bostonfrom $51
Flights to Atlantafrom $46
Flights to Dallasfrom $57
Flights to Seattlefrom $58