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$328+ Cheap flights from Watertown, NY (ART) to Massachusetts

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 12/2. Fares are subject to change and may not be available on all flights or dates of travel.
ART — BOS
Dec 19 — Dec 261
Fri 12/19
Fri 12/26
1 adult, Economy
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Find flight deals from Watertown to Massachusetts

Cheapest flights from Watertown to Massachusetts
Explore the most affordable flight options available from Watertown to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 19, 2025.

This American Airlines deal was found by Cheapflights users on 11/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/26:00 amART - BOS
1 stop6h 22mAmerican Airlines
Sat 12/64:10 pmBOS - ART
1 stop6h 53mAmerican Airlines
Deal found 11/17$328
This American Airlines deal was found by Cheapflights users on 11/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/186:00 amART - BOS
1 stop6h 22mAmerican Airlines
Wed 11/198:00 amBOS - ART
1 stop6h 08mAmerican Airlines
Deal found 11/17$736

Cheap flight deals from Watertown to Massachusetts

Keep the following information in mind while searching for Watertown to Massachusetts flight deals. Data was last updated November 19, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$328
(American Airlines)
Provider with most accurate pricing for Watertown-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Watertown-Boston Logan Intl flights.
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From Watertown to Massachusetts
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Watertown 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 November 19, 2025.
Use the filters below to find and compare flights from Watertown to Massachusetts that are best for you.

Fly from

Watertown

Fly to

Massachusetts

Route

Depart

Return

Price

WatertownBoston

ART - BOS

ARTBOS

Watertown

Tue 12/2

2:33 pm-11:50 pm

2 stops9h 17m

Boston Logan Intl

Sat 12/6

4:10 pm-11:03 pm

1 stop6h 53m

$334

WatertownBoston

ART - BOS

ARTBOS

Watertown

Fri 3/13

4:37 pm-10:24 pm

1 stop5h 47m

Boston Logan Intl

Tue 3/17

11:23 am-2:55 pm

1 stop3h 32m

$476

WatertownBoston

ART - BOS

ARTBOS

Watertown

Tue 2/17

6:00 am-10:34 am

1 stop4h 34m

Boston Logan Intl

Wed 2/18

6:49 pm-10:56 pm

1 stop4h 07m

$736

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/17

Best time to book a flight from Watertown to Massachusetts

Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Watertown 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 Watertown to Massachusetts

What is the cheapest month to book a flight from Watertown, New York to Massachusetts?

Currently, January is the cheapest month in which you can book a flight from Watertown, New York to Massachusetts (average of $63). Flying from Watertown, New York to Massachusetts in October is currently the most expensive (average of $128). 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 Watertown 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 Watertown to Massachusetts?

    Watertown (ART), located 5.6 mi from the city center, is the airport you fly out of when you book flights from Watertown to Massachusetts.

  • How long is the flight from Watertown, New York to Massachusetts?

    For as low as $334, American Airlines can have you in Massachusetts from Watertown, New York in 9h 17m. Watertown, New York and Massachusetts are separated by a distance of 276 mi.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Watertown 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 Watertown, New York to Massachusetts?

    Currently, January is the cheapest month in which you can book a flight from Watertown, New York to Massachusetts (average of $63). Flying from Watertown, New York to Massachusetts in October is currently the most expensive (average of $128). 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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