$76 Cheap flight deals from New York (NYC) to Great Diamond Island (PWM)
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This Weekend's Flight Deals from New York to Great Diamond Island
This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$257 Roundtrip, found 1 day ago
$257
Roundtrip
found 1 day ago
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$284 Roundtrip, found 3 days ago
$284
Roundtrip
found 3 days ago
LGA
LaGuardia
PWM
Portland Intl. Jetport
$340 Roundtrip, found 2 days ago
$340
Roundtrip
found 2 days ago
HPN
Westchester County
PWM
Portland Intl. Jetport
$1,108 Roundtrip, found 6 days ago
$1,108
Roundtrip
found 6 days ago
Airfares from $76 One Way, $161 Round Trip from New York to Great Diamond Island
Prices starting at $161 for return flights and $76 for one-way flights to Great Diamond Island were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
JFK
New York
PWM
Portland
$161 Roundtrip, found 1 day ago
$161
Roundtrip
found 1 day ago
EWR
New York
PWM
Portland
$165 Roundtrip, found 1 day ago
$165
Roundtrip
found 1 day ago
JFK
New York
PWM
Portland
$169 Roundtrip, found 1 day ago
$169
Roundtrip
found 1 day ago
EWR
New York
PWM
Portland
$174 Roundtrip, found 1 day ago
$174
Roundtrip
found 1 day ago
JFK
New York
PWM
Portland
$181 Roundtrip, found 6 hours ago
$181
Roundtrip
found 6 hours ago
Great Diamond Island economy flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Chebeague Island Inn
8.8/10 Excellent! (77 reviews)
Jul 18 - Jul 21
3 night stay
Islip (ISP) to Portland (PWM)
Southwest Airlines • Non-stop roundtrip • Coach
Price was $983, price is now $799 per person
$799
per person
found 2 hours ago
Such a beautiful place! We had a great time riding bikes around the island.
Reviewed on Jun 18, 2019
2.5-star property
The Meadowmere Resort
8.6/10 Excellent! (1,000 reviews)
Jul 24 - Jul 27
3 night stay
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
United • Roundtrip • Coach
Price was $1,663, price is now $1,218 per person
$1,218
per person
found 1 day ago
The staff was very nice, greeted us with complimentary champagne. Location was perfect, easy to walk downtown and to the Marginal Way. Beds were very comfortable. The weather was very hot, and the AC was a swamp cooler on the floor and very loud. We put up the sign on our door for Housekeeping, but they only changed out our towels. After that, we just didn’t bother.
Reviewed on Aug 5, 2025
3.0-star property
Ogunquit River Inn & Suites
9/10 Wonderful! (1,007 reviews)
Jul 18 - Jul 21
3 night stay
Islip (ISP) to Portland (PWM)
Southwest Airlines • Non-stop roundtrip • Coach
Price was $1,161, price is now $867 per person
$867
per person
found 2 hours ago
Excellent location and beautiful views
Reviewed on Sep 14, 2025
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View all tripsGreat Diamond Island first class flight packages
Price found within the past 48 hours. Click for updated prices.
3.5-star property
Inn at Diamond Cove
8.8/10 Excellent! (195 reviews)
Jul 24 - Jul 26
2 night stay
New York (LGA) to Portland (PWM)
American Airlines • Roundtrip • FirstClass
Price was $1,320, price is now $1,201 per person
$1,201
per person
found 1 day ago
The Inn itself is gorgeous on a lovely quiet island for some exploring. The rooms are large and well maintained, and the staff while inexperienced does their best to help and answer questions.
Our room was ready when we got there early, and they let us check-in a few hours ahead which was greatly appreciated.
The pool is nice (a little chilly) and the hot tub was boiling, and we enjoyed relaxing by the pool. The beaches are nice to visit from a short walk but don't expect sandy beaches here.
We walked around the island, even outside of the homeowner's association barrier and there is a nice gift shop where you can get ice cream, popsicles and some treats for ~1 a pop. Surprisingly reasonable for this island.
The main issue with the island is food as one might expect, so just keep you expectations on the lower end (unlike the higher side prices) and you won't be too disappointed. The hotel restaurant is OK - the pancakes were at least good - but the two island restaurants left a lot to be desired.
Would we return? I think if you are looking for a short getaway or are willing to go to portland for food, it can make an excellent relaxing trip.
Reviewed on Jul 26, 2024
3.5-star property
The Docent's Collection at 121 Middle Street
9.6/10 Exceptional! (324 reviews)
Jul 24 - Jul 26
2 night stay
New York (LGA) to Portland (PWM)
American Airlines • Roundtrip • FirstClass
Price was $2,067, price is now $1,808 per person
$1,808
per person
found 1 day ago
This place is a hidden gem! Absolutely beautiful, convenient and waking distance to the pier/waterfront. Room was immaculate and staff very responsive. Highly recommend!
Reviewed on Mar 31, 2026
2.5-star property
Hampton Inn Portland Downtown - Waterfront
8.8/10 Excellent! (1,003 reviews)
Jul 24 - Jul 26
2 night stay
New York (LGA) to Portland (PWM)
American Airlines • Roundtrip • FirstClass
Price was $1,592, price is now $1,423 per person
$1,423
per person
found 1 day ago
Just a one night stay with family, but the staff at front desk was great. The rooms were clean and big. They offer a breakfast buffet in the morning and coffee is available most of the day.
Reviewed on May 8, 2026
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View all tripsMore About Flying To Great Diamond Island from New York
Route Information for Flights from New York to Great Diamond Island
Origin Airport IATA Code | NYC |
|---|---|
Destination Airport IATA Code | PWM |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
New York to Great Diamond Island
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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.