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

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street, Portland, ME
Fully refundableReserve now, pay when you stay
The price is ￥18,149 per night from Nov 16 to Nov 17
￥18,149
￥25,958 total
Nov 16 - Nov 17
includes taxes & fees
9.2/10 Wonderful! (1,666 reviews)
Great rooms, walk-able to everything, super clean, great staff, the restaurant is delicious and the bar has good drinks, very accommodating and lots of extras! The 4 stars are for parking... we would like to keep our car inside the garage, to do so it must be valet, that is not an option for some ...

Reviewed on Nov 12, 2025

Portland Harbor Hotel
Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is ￥12,772 per night from Nov 18 to Nov 19
￥12,772
￥14,130 total
Nov 18 - Nov 19
includes taxes & fees
7.8/10 Good! (1,222 reviews)
I've stayed here a few times and have always had a good experience. Staff is always welcoming and the rooms are

Reviewed on Nov 9, 2025

Clarion Hotel Portland
Tru by Hilton Portland Airport Area

Tru by Hilton Portland Airport Area

2.5 out of 5
369 Maine Mall Road, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is ￥12,202 per night from Nov 30 to Dec 1
￥12,202
￥13,300 total
Nov 30 - Dec 1
includes taxes & fees
8.8/10 Excellent! (1,609 reviews)
Absolutely

Reviewed on Nov 12, 2025

Tru by Hilton Portland Airport Area
See all 2,272 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

Eastern Promenade showing a bay or harbor and general coastal views as well as a small group of people

Eastern Promenade

Built on an old rail corridor along the easternmost portion of Portland’s peninsula, this waterfront trail offers stunning views of the harbor and Atlantic Ocean.

Eastern Promenade

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

International Cryptozoology Museum

You can spend time browsing the exhibits at International Cryptozoology Museum in Portland. Stroll along the area's waterfront or experience its acclaimed theater scene.

International Cryptozoology Museum

What to do in Great Diamond Island

Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

￥2,594
per traveler
Portland Smartphone Audio Tour: Self-Guided Drive
Ultimate Portland Self-Guided Driving GPS Audio Tour

Ultimate Portland Self-Guided Driving GPS Audio Tour

￥2,594
per traveler
100% of travellers recommend
Ultimate Portland Self-Guided Driving GPS Audio Tour
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour

Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour

￥1,506
per traveler
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour
See all activities in Great Diamond Island

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.

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