Great Diamond Island Vacations

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Find the Best Great Diamond Island Vacation Packages

Great Diamond Island Hotel Deals

The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
Fully refundableReserve now, pay when you stay
The price is AED 360 per night from Feb 24 to Feb 25
AED 360
AED 398 total
24 Feb - 25 Feb
includes taxes & fees
8.8/10 Excellent! (1,005 reviews)
The room was clean and comfortable. Thr hotel itself was beautiful

Reviewed on 4 February 2026

The Westin Portland Harborview
Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
The price is AED 283 per night from Feb 19 to Feb 20
AED 283
AED 313 total
19 Feb - 20 Feb
includes taxes & fees
8/10 Very Good! (1,351 reviews)
Great location great staff everything functioned.

Reviewed on 6 February 2026

Clarion Hotel Portland Airport ME
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (1,751 reviews)
Wonderful stay!

Reviewed on 7 February 2026

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Portland Harbor Hotel
See all 2,265 properties in Great Diamond Island
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Discover the most popular places to visit in Great Diamond Island

Portland Museum of Art showing art and interior views as well as a small group of people

Portland Museum of Art

4.5/5(255 reviews)

You can spend an afternoon studying the exhibits at Portland Museum of Art during your trip to Portland. Stroll along the area's waterfront or experience its entertainment choices.

Portland Museum of Art
East End Beach which includes general coastal views and a beach as well as a small group of people

East End Beach

If a restful vacation is part of your travel plans, East End Beach might be the perfect place to seek out during your trip to Portland.

East End Beach
Wadsworth-Longfellow House showing interior views, heritage elements and a house

Wadsworth-Longfellow House

4/5(78 reviews)

You can spend an afternoon exploring the galleries in Wadsworth-Longfellow House during your trip to Portland. Stroll along the area's waterfront or experience its great live music.

Wadsworth-Longfellow House

Frequently asked questions

How do I find cheap flights to Great Diamond Island that have flexible change policies?
At Expedia, we've been channeling our inner gymnast to offer you the most flexible airfares on the market. Simply click on "No change fee" directly under the filter heading "Flexible change policies" to find your ideal flight to Great Diamond Island.
Which airlines fly to Great Diamond Island?
With a great selection of airlines that fly into or near Great Diamond Island, you have plenty of options:

  • American Airlines - 225 flights to or near Great Diamond Island each month, including 225 flights to Portland Intl. Jetport Airport (PWM) per month.
  • Delta - 208 flights to or near Great Diamond Island each month, including 208 flights to Portland Intl. Jetport Airport (PWM) per month.
  • United Airlines - 164 flights to or near Great Diamond Island each month, including 164 flights to Portland Intl. Jetport Airport (PWM) per month.

How can I find cheap tickets to Great Diamond Island?
An useful strategy for nabbing cheap tickets is to be flexible with your dates. Start by searching for your flight to Great Diamond Island, then click on the "flexible dates" box for a list of prices for nearby days. Another tip? Book ahead of time. To give you an idea of costs, was the best price for a flight to Great Diamond Island in the last seven days.
How much is a flight to Great Diamond Island?
One-way flights leaving () sold for as little as in the last seven days. During this time, the price of a round-trip fare to Great Diamond Island ranged between and . If you find a fantastic deal, grab it quickly — these fares don't hang around.
What are the most popular airports to fly into in Great Diamond Island?
The main entryway to Great Diamond Island, around 776 flights taxi into Portland Intl. Jetport Airport (PWM) every month. Find an unbeatable deal, reserve your seat and prepare to discover this wonderful region.
When is the cheapest time to fly to Great Diamond Island?
Take off to Great Diamond Island earlier in the week and you'll usually be rewarded with lower fares. Tuesday is typically the cheapest day to hop on a plane, with Monday a close second. If you want to avoid the priciest flights, stay away from Saturdays.
How much is a plane ticket to Great Diamond Island?
In the last seven days, airfares to Great Diamond Island varied between and . The early bird catches the worm, so land yourself a terrific deal today.
What months are the cheapest to book a flight to Great Diamond Island?
February is the best month to reserve a seat for your Great Diamond Island vacation. Tickets are at their most expensive during the festive month of December, so keep clear of this time if possible.
How long is a flight to Great Diamond Island?
It depends on a number of things, including your point of departure and whether it's a direct or multi-stop flight. Below are three of the leading domestic routes to Great Diamond Island and their average flight durations:

  • Washington, DC (DCA-Ronald Reagan Washington National) to Portland Intl. Jetport Airport (PWM) - 1 hour and 44 minutes
  • Newark, NJ (EWR-Liberty Intl.) to Portland Intl. Jetport Airport (PWM) - 1 hour and 25 minutes
  • Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall) to Portland Intl. Jetport Airport (PWM) - 1 hour and 28 minutes