Great Diamond Island Vacations

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Photo by Robbie Martin

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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 ₩143,898 per night from Feb 8 to Feb 9
₩143,898
₩159,208 total
Feb 8 - Feb 9
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
What a great stay and great breakfast

Reviewed on Jan 18, 2026

The Westin Portland Harborview
Long Creek Hotel by IHG

Long Creek Hotel by IHG

2.5 out of 5
171 Philbrook Ave South Portland ME
Fully refundable
The price is ₩114,531 per night from Jan 27 to Jan 28
₩114,531
₩124,838 total
Jan 27 - Jan 28
includes taxes & fees
7.4/10 Good! (1,008 reviews)
Clean spacious room. Mostly friendly staff.

Reviewed on Jan 16, 2026

Long Creek Hotel by IHG
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 ₩114,825 per night from Jan 25 to Jan 26
₩114,825
₩127,042 total
Jan 25 - Jan 26
includes taxes & fees
8/10 Very Good! (1,328 reviews)
The pool was great!

Reviewed on Jan 19, 2026

Clarion Hotel Portland Airport ME
See all 2,264 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

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

Wadsworth-Longfellow House

4/5(78 reviews)

As you tour this historic brick home, trace three generations of Maine family history and learn about the cultural and political impact of its family members.

Wadsworth-Longfellow House

Merrill Auditorium

4/5(15 reviews)

You can enjoy a show at Merrill Auditorium during your trip to Portland. Stroll along the area's seaside or experience its entertainment choices.

Merrill Auditorium

Maine Narrow Gauge Railroad Company and Museum

You can spend an afternoon studying the exhibits at Maine Narrow Gauge Railroad Company and Museum in Portland. Experience the area's great live music and acclaimed theater scene.

Maine Narrow Gauge Railroad Company and Museum

Frequently asked questions

Can I cancel my flight booking to Great Diamond Island due to COVID-19?
If you've yet to book your tickets, scan the terms and conditions of your preferred airline. If you've already locked in your flight to Great Diamond Island, visit our Customer Service Portal. The information here will help you work out which COVID-19 policies are applicable to your reservation and advise the next steps.
What's the best way to find cheap flights to Great Diamond Island that have flexible change policies?
By using our neat "No change fee" filter, that's how. Just type in your travel dates, click "Search," then tick the checkbox under the "Flexible change policies" heading (it's on the top left of your screen). Expedia makes it a cinch to find flexible, low-priced tickets to Great Diamond Island.
What are some of the general tips for travelers to Great Diamond Island during the COVID-19 outbreak?
As a result of COVID-19, traveling today comes with more challenges. Have a read over these valuable tips before jumping on your flight to Great Diamond Island:
  • Before you lock in a flight, see if any travel restrictions apply — in both your destination and origin. Keep informed with the latest updates by checking government travel advisories.
  • Wear a face mask even during airport screening. A TSA employee will ask you to temporarily lower your mask for identification purposes.
  • Avoid handing your boarding pass directly to a TSA employee. Rather, you should position the pass on the reader and then hold it up for inspection.
  • TSA is now allowing passengers to take one container of hand sanitizer, up to 12 oz (350 ml) in size, in carry-on luggage. This will have to be removed from your bag and presented for screening.
  • To minimize handling during screening, place personal items such as your phone, coins and keys into your carry-on rather than into the bins.
  • Transport your food items in a clear plastic bag and also put them in a screening bin. Keeping food separate from your carry-on makes it less likely that a TSA agent will need to open your bag for inspection.

Which airlines fly to Great Diamond Island?
Southwest Airlines operates flights into or near Great Diamond Island, including 182 that touch down at Portland Intl. Jetport Airport (PWM) each month. Pick your vacation dates and then book your seat early for an unbeatable deal.
How can I find cheap tickets to Great Diamond Island?
One of the easiest ways to score cheap tickets to Great Diamond Island is to be flexible with your travel dates. Search for your flights, then click "flexible dates" above the results. It'll bring up the cheapest prices for nearby days. The best price for a flight to Great Diamond Island in the last seven days was . Booking ahead of time will usually help you pick up an even bigger bargain.
How much is a flight to Great Diamond Island?
One-way flights departing from () sold for just in the last seven days. During this time, the cost of a return ticket to Great Diamond Island varied between and . If you spot a bargain ticket, book ASAP — these fares don't wait around for long.
What are the most popular airports to fly into in Great Diamond Island?
Start arranging your Great Diamond Island adventure by reserving a seat on one of the 1571 flights every month to Portland Intl. Jetport Airport (PWM). This is the region's main point of entry.
When is the cheapest time to fly to Great Diamond Island?
Take off to Great Diamond Island early on in the week and you'll usually be rewarded with lower-cost fares. Tuesday is known for being the cheapest day to hop on a plane, closely followed by Monday. If you're eager to avoid the priciest flights, give Saturdays a wide berth.
How much is a plane ticket to Great Diamond Island?
In the last seven days, ticket prices to Great Diamond Island ranged from to .
Which airlines with flights to Great Diamond Island employ COVID-19 cleanliness policies?
In response to the global COVID-19 pandemic, many airlines have adopted additional actions and measures to help travelers get back in the skies. These carriers include:
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.