Find cheap flights from New Windsor to Massachusetts

Find cheap flights from New Windsor to Massachusetts

Round-trip
Economy
New Windsor (SWF)
Massachusetts
Thu 12/3
Thu 12/10
Any month
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Top tips for finding cheap flights to Massachusetts

  • Book at least 3 weeks before departure in order to get a below-average price.
  • High season is considered to be March, April and May. The cheapest month to fly to Massachusetts is February.
  • Morning departure is around 1,117% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs - booking Massachusetts flights

How long is the flight to Massachusetts from New Windsor?

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Top airline flying New Windsor Stewart to Massachusetts

Scores according to KAYAK customer reviews

7.2
Allegiant Air
Overall score based on 1,957 reviews
7.7
Boarding
7.0
Comfort
8.1
Crew
6.1
Entertainment
6.4
Food
Airline reviews

Cons: "Great price. Wonderful flight. Seats are so close knees touched the whole flight."

Pros: "Crew was Aamazzing! Went above and beyond even to sit with one of kids while I used restroom, put my kids at ease, went above and beyond to make sure at such a tender age that they were okay! Made me very happy with allegiant and happy that I chose them!"
Cons: "It’d be cool to see more inflight services some day? As in maybe WiFi at a cost or TVs, seat recliner"

Pros: "Comfortable leg room"
Cons: "Delayed as usual"

Cons: "A place to out my bottle of water"

Pros: "Florida was amazing. The people were very friendly."
Cons: "Nothing"

Cons: "I would have liked to have a drink of water for free!!"

Pros: "The crew was good and the flight was smooth."
Cons: "The seats were far too close to have any kind of real comfort."

Pros: "There was nothing outstanding really"
Cons: "It’s a low cost airline, so expectations are very low. Plane was very dirty because it just keeps on hopping back and forth without any cleaning service it seems"

Pros: "Comfortable and inexpensive tickets"
Cons: "It was all good!"

Pros: "No leg room & very misbehaved children sitting behind me. The children screamed the whole time, kicked our seats, and the mother had no control. If you are any taller than 5’9”, you may want to consider an exit row seat to have room for your legs. My knees were jammed in to the seat in front of me."

Pros: "Great fares even for last minute booking."
Cons: "Services and comfort as expected for the price."

Cons: "Delayed due to weather"

Pros: "Nice pilot and crew."
Cons: "The warning about alcohol was a bit sarcastic, but I guess in today's world people who have acted out are the real culprits..."

Pros: "Definitely the price. Boarding process was pretty quick. Flight attendants seemed nice."
Cons: "Left a little late, but still arrived on time, so that was okay. Seats aren't the most comfortable, but that's expected. Was still able to get a little nap in."

Pros: "The crew was courteous and helpful; plane was clean; flight was on time; no problems"

Pros: "Very efficient. You cannot beat the price. All I expected is to get there."
Cons: "The plane was very clean and looked new, the seats were comfortable but did not recline. I missed that."

Pros: "All went well. No real disappointments!"
Cons: "A little cramped but not terrible. Would like to know kayak fee up front before booking and all hidden charges!"

Pros: "Crew friendly and professional"
Cons: "Everything is extra, even water or soda. Seats are narrow so glad im not a heavier person"

Cons: "I dislike their pricing structure."

Pros: "Going in & out of small airports."
Cons: "We arrived late. Pricing system."

Cons: "4 hours late. No explanation. I have flown Allegiant 3 times. Late twice."

Pros: "Passengers were fun"
Cons: "Need entertainment"

Pros: "Crew likes to have fun with their passengers -- making the whole experience that much more enjoyable. It's a budget airline so you have to pay for things like refreshments and snacks (also, carryons and if you want you boarding pass printed at the airport) -- but don't let that sway you! All it takes is a little prior organization (we packed a couple of sandwiches and printed our passes at home, plus packed very light). Overall a great experience."

Pros: "Keep the free snacks and drinks, NA or soda, I really just miss the legroom (nearly 6’ tall) and cushions, a chair that can ease back a bit. All airlines do this but you are worse than frontier, the major carriers have skimped but not like this."
Cons: "3 hour torture chamber. When she said it was their goal to make us comfortable, but more importantly to keep us safe I snorted laughter. It was a bit better and a lot shorter than the dark passage"

Cons: "Lost my bag"

Cons: "15 minutes waiting for luggage—still none out."

Pros: "Everything. Boarding stared early and, although the plane was full, everyone was seated and ready for on time takeoff"
Cons: "Plan to curtail service at AVP! Planes are always full!!"

Pros: "New plane!"
Cons: "Boarded too early!"

Pros: "Cost"
Cons: "Left late"

Cons: "Sent email out asking for volunteers to reschedule her flight. Got on the plane our seats were not the same as selected. And we paid more to select our seats. Friend of ours seat was switched also and instead of him sitting next to his wife he sat next to a person who did not have an assigned seat he was extremely large and he was hanging off The seat into the aisle I noticed an empty seat and had to ask the stewardess if he could switch seats instead of the stewardess offering on her own. The flight out was delayed approximately one hour various mechanics coming on and off plane until finally we were able to leave."

Cons: "Bought flight insurance. Had to cancel within one week due to mom's health issues. Could not get a refund without her Dr.'s signature, which was impossible for me to do. Therefore....lost 145.....down the drain....."

Cons: "All of the hidden fees. I was initially charged more than $200 over the price I was quoted on Kayak.com and then had to pay an extra $45 to bring 1 carry-on each. I do not plan to use Kayak.com again for these reasons and will not recommend this site to anyone"

Pros: "Great flight!"
Cons: "Price, service"

Pros: "Cleanliness, friendliness, on time."
Cons: "Charging for drinks and snacks snacks.."

Cons: "Flight was delayed almost 3 hours and the plane itself was noisy."

Cons: "No wifi"

Pros: "While I enjoy the fact that Allegiant offers direct flights to Laredo at an affordable price, the planes really need to be updated."
Cons: "We really disliked that we boarded the plane and just before taking off they made us get off again and never did confirm the real reason. The planes really need better maintenance since this is the second time in two weeks we have to change planes due to problems."

Pros: "Nothing about this flight experience was good, with the exception of my overpriced hummus and crackers."
Cons: "Boarding was slow and archaic. Once we were all finally seated they came through 3 times with a paper trying to figure out who wasn't on board. As we taxied towards the runway a lady who felt dizzy coming on board threw up. The crew was obviously panicked and unorganized. We taxied back to our gate and waited for LA Fire for. to escort the ill lady off and clean the area. While waiting to taxi out the second time the flight attended, Tyeesha, was very rude to an elderly gent. He was seated in an exit row and she didn't think him capable. The lady on the aisle of my row volunteered to switch and Tyeesha' s response was a sharp, "Do you want to pay the higher price too?" When the lady next to me said she would gladly pay Tyeesha announced loudly that this discussion was between the two of them and everyone else needed to mind their own business. The lady offering to switch was really embarrassed, as was the elderly gent. Someone else was made to switch with him. They looked disgruntled too. In the air all the flight attendants were sharp and very direct. There were no please or thank you's used. Trash was collected silently and mostly with pointing. The armrest to my left had five flavors of chewed gum stuck to the side of it. My lap tray had grey and yellow sticky stuff on it and I chose to hold my food rather than let the two touch. The floors were untidy. The only reason I will ever fly Allegiant again is if I have no other options. It is 60 minutes closer to my house than SLC and I will be making the drive from now on."

Pros: "Seats were clean and nice"
Cons: "One crew member clearly is a disgruntled employee. It also should be against the law not to provide water without payment."

Pros: "The plane departed on time. The crew was very friendly."

Cons: "The flight got cancelled - trip had to be completely rearranged."

Cons: "Arrival in Ft Lauderdale... Bags took an hour to get to carrousel. Never were posted on the information. Flight were, as expected, uncomfortable."

Pros: "Crew was amazing & child friendly."

Pros: "I liked how friendly the staff were and how everything was done on time."

Pros: "Really smooth flight, quick and easy to Las Vegas..."
Cons: "Paying for checked luggage..."

Pros: "Highly recommend"

Pros: "Everything was fine"
Cons: "Hard landing"

Pros: "Having to bug hotel staff to make sure to print boarding passes to avoid a $5 charge for each...having to pay for carry-on bags in advance and then unstuff them in the cramped aisles while boarding because the overhead compartments were too small...flight delays on each leg of the trip...staff that seemed lobotomized...seats that have a bar jamming into your lower back and don't recline.... etc., etc, etc, etc, Plus stupid coporate name and a logo that's hard on the eyes! ALLEGIANT SUCKS from its nose to its tail fin."

Pros: "Not much"
Cons: "6hr delay, boarded the plane 3 separate times. 2 different mechanical problems. Infrequent updates"

Read more about Allegiant Air

Book cheap flights from New Windsor to Massachusetts

Recent round-trip flight deals

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Recent one-way flight deals

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