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.
Admiral Peary Inn

Admiral Peary Inn

3 out of 5
Price was CA $1,938, price is now CA $1,236 per person
CA $1,236
per person
Jul 26 - Aug 2
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9/10 Wonderful! (49 reviews)
Good price, quiet property. They do state somewhere in their web page that they're no longer a bed and breakfast, it would be better to really put that up front, perhaps take the bed and breakfast sign down from inside the kitchen. It was nice to have tea and coffee, thank you. Surprising, but not totally unusual in this day and age to not see a single person from the property, that all contact was done via notes.

Reviewed on Jun 18, 2026

The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was CA $3,927, price is now CA $2,570 per person
CA $2,570
per person
Jul 26 - Aug 2
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
8.6/10 Excellent! (1,000 reviews)
Price was good for the amenities offered and location. Our room was just recently renovated.

Reviewed on Jun 22, 2026

Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Moody
Price was CA $3,264, price is now CA $2,168 per person
CA $2,168
per person
Jul 26 - Aug 2
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9/10 Wonderful! (1,011 reviews)
This ida beautiful hotel close to all beaches, dining, and shopping in ogunquit and wells. It is unique because it sits on a hill. Everything was great. The only reason for 4 stars is all the stairs. Be sure you know where your room is located because you might end up dragging your stuff up and down some steep and lengthy stair cases.

Reviewed on Jun 24, 2026

Dormir

Dormir

3 out of 5
Price was CA $2,024, price is now CA $1,447 per person
CA $1,447
per person
Jul 26 - Aug 2
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
8.8/10 Excellent! (1,006 reviews)
Clean room. Breakfast selection. Clean facilities. Parking was good.

Reviewed on Jun 22, 2026

Ocean Gate Inn

Ocean Gate Inn

3 out of 5
Price was CA $2,048, price is now CA $1,546 per person
CA $1,546
per person
Jul 26 - Aug 2
found 15 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
8.6/10 Excellent! (1,001 reviews)
What a hidden gem in the area! We loved this beautiful property

Reviewed on Jun 23, 2026

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Great Diamond Island Hotel Deals

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

3 out of 5
340 Park Ave Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $226 per night from Jun 28 to Jun 29
CA $226
CA $250 total
Jun 28 - Jun 29
includes taxes & fees
8.6/10 Excellent! (2,185 reviews)
"Stay away from this place. They charge you to park in their lot. And the worst part is that the room was dirty & the sheets looked they haven’t been changed. They had hair on the sheets & the pillows were also smelly & im not sure what they were stuffed with. It’s not close by to any places to eat. ..."

Reviewed on Jun 24, 2026

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
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 $367 per night from Jun 28 to Jun 29
CA $367
CA $461 total
Jun 28 - Jun 29
includes taxes & fees
9.4/10 Exceptional! (1,777 reviews)
"Did not like that our room was next to the bar across the street. Heard the music until 1 AM Only stayed one night or we would have requested another room."

Reviewed on Jun 24, 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 $358 per night from Jun 28 to Jun 29
CA $358
CA $435 total
Jun 28 - Jun 29
includes taxes & fees
9.4/10 Exceptional! (1,255 reviews)
"Love everything about this place. The Staffs, Cleanliness, and Location. All Amazing."

Reviewed on Jun 24, 2026

Cambria Hotel Portland Downtown-Old Port
See all 2,439 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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All Inclusive Vacations
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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
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
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

What to do in Great Diamond Island

Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

CA $24
per traveller
100% of travellers recommend
Portland Smartphone Audio Tour: Self-Guided Drive
Maine Whale Watching Tour in Portland

Maine Whale Watching Tour in Portland

CA $179
per adult
Maine Whale Watching Tour in Portland
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.