Great Diamond Island Vacation Packages

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Top Great Diamond Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Price was CA $1,351, price is now CA $961 per person
CA $961
per person
Aug 7 - Aug 9
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Portland (PWM)
9/10 Wonderful! (1,007 reviews)
Patrick was great and helped us out a lot. He gave us suggestions somewhere to eat.

Reviewed on May 31, 2026

Cliff House Maine

Cliff House Maine

4.5 out of 5
Bald Head
Price was CA $2,655, price is now CA $1,922 per person
CA $1,922
per person
Jul 26 - Jul 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (1,002 reviews)
Staff was very helpful. Polite and friendly.

Reviewed on May 20, 2026

The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was CA $1,392, price is now CA $1,019 per person
CA $1,019
per person
Jul 18 - Jul 20
found 3 hours ago
Roundtrip flight included
Montreal (YUL) to Portland (PWM)
8.6/10 Excellent! (1,000 reviews)
The room was recently renovated and was immaculate. The beds and pillows were very good, as was the shower pressure. The chairs were uncomfortable. There needs to be handicapped parking available near the rooms. I would not recommend the Pub. The service was excellent, but the food was subpar.

Reviewed on May 30, 2026

Inn By The Sea

Inn By The Sea

4 out of 5
Price was CA $2,418, price is now CA $2,065 per person
CA $2,065
per person
Jul 26 - Jul 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (315 reviews)
Very nice place, very cclean and friendly.

Reviewed on May 30, 2026

Chebeague Island Inn

Chebeague Island Inn

4 out of 5
Price was CA $1,433, price is now CA $1,284 per person
CA $1,284
per person
Jul 26 - Jul 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
8.8/10 Excellent! (77 reviews)
Charming and easy access to the Golf Course

Reviewed on Sep 21, 2025

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Great Diamond Island Hotel Deals

Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Fully refundable
The price is CA $164 per night from Jun 15 to Jun 16
CA $164
CA $181 total
Jun 15 - Jun 16
includes taxes & fees
8/10 Very Good! (1,472 reviews)
"This hotel was bad from the minute we arrived. I called early in week to see if there was a possibility to check in early because we had a long ride & had to catch a ferry for a memorial for a boss in Peaks Island, ME. When we arrived the 2 at front desk kind of laugh at me & looked at me like I ..."

Reviewed on Jun 1, 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
The price is CA $345 per night from Jun 7 to Jun 8
CA $345
CA $435 total
Jun 7 - Jun 8
includes taxes & fees
9.4/10 Exceptional! (1,761 reviews)
"Very friendly staff."

Reviewed on Jun 1, 2026

Portland Harbor Hotel
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
Fully refundable
The price is CA $364 per night from Jun 15 to Jun 16
CA $364
CA $440 total
Jun 15 - Jun 16
includes taxes & fees
9.4/10 Exceptional! (1,226 reviews)
"Hotel was updated, clean and nice. Parking on site is great. The 'food credit' is really frustrating. I was forced to pay $25 for food I didn't really want. I would prefer that not be a forced fee."

Reviewed on Jun 1, 2026

Cambria Hotel Portland Downtown-Old Port
See all 2,337 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.
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Discover the most popular places to visit in Great Diamond Island

State Theatre

State Theatre

The beautiful mix of architectural styles, from Art Deco to Moorish, makes this newly renovated performing arts venue one of New England’s best.

State Theatre
Portland Museum of Art

Portland Museum of Art

Maine’s largest and oldest art institution showcases three centuries of American art and European masters in its architecturally impressive museum complex.

Portland Museum of Art
East End Beach

East End Beach

Swim in the Atlantic Ocean, stroll along the sand-and-pebble shoreline or enjoy a picnic with unbeatable views at Portland’s public beach.

East End Beach

What to do in Great Diamond Island

Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

CA $21
per traveller
Portland Smartphone Audio Tour: Self-Guided Drive
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.

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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.