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.
The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Price was CA $1,529, price is now CA $1,141 per person
CA $1,141
per person
Apr 19 - Apr 25
found 11 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Portland (PWM)
9.6/10 Exceptional! (249 reviews)
Check-in and check-out are a breeze, easy access to a city parking lot on the block (needed as there was a snow ban on parking when I visited!). In terms of the space itself - clean, well appointed, spacious. Honestly a treat to stay here!

Reviewed on Feb 23, 2026

Cliff House Maine

Cliff House Maine

4.5 out of 5
Bald Head
Price was CA $3,351, price is now CA $2,251 per person
CA $2,251
per person
Apr 19 - Apr 25
found 11 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Portland (PWM)
9.4/10 Exceptional! (1,001 reviews)
Great hotel with super nice views!

Reviewed on Mar 1, 2026

84 Main

84 Main

4 out of 5
Price was CA $1,463, price is now CA $1,178 per person
CA $1,178
per person
Apr 2 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
10/10 Exceptional! (52 reviews)
Very spacious and relaxing. Nice view of Kennebunk quaint ice rink and Main Street. Coffee shop at Street level was a fantastic add! Beds and bedding were comfortable. Will visit again! Nothing lacking with respect to amenities.

Reviewed on Dec 29, 2025

Inn By The Sea

Inn By The Sea

4 out of 5
Price was CA $1,593, price is now CA $1,373 per person
CA $1,373
per person
Apr 2 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9.4/10 Exceptional! (288 reviews)
Inn by the Sea was an excellent place to stay. The front desk during check-in was 5 star and very helpful. Our room was clean, cozy and comfortable. The spa was wonderful and relaxing. The restaurant food was delicious, a lot of variety. I would recommend the Inn By The Sea to my friends and family.

Reviewed on Mar 1, 2026

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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 CA $134 per night from Mar 18 to Mar 19
CA $134
CA $148 total
Mar 18 - Mar 19
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
Clean, quiet and comfortable. Exceptional team who were helpful and friendly. I actually hated to leave. Great stay!

Reviewed on Feb 28, 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 CA $105 per night from Mar 5 to Mar 6
CA $105
CA $116 total
Mar 5 - Mar 6
includes taxes & fees
8/10 Very Good! (1,387 reviews)
Nothing saying on page that boiler is broken no hot showers pool ice cold hot tub ice cold crack heads everywhere. This place has gone completely to hell just from last year will never be staying at this location again. Not to add messed up my rooms put me in a double bed instead of my king ...

Reviewed on Mar 2, 2026

Clarion Hotel Portland Airport ME
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 $124 per night from Mar 26 to Mar 27
CA $124
CA $175 total
Mar 26 - Mar 27
includes taxes & fees
9.4/10 Exceptional! (1,168 reviews)
Easy check in and friendly staff. Food was good room was big and with nice view.

Reviewed on Mar 2, 2026

Cambria Hotel Portland Downtown-Old Port
See all 2,244 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 showing street scenes as well as an individual female

State Theatre

4.5/5(5 reviews)

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 which includes interior views and art as well as a small group of people

Portland Museum of Art

5/5(5 reviews)

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 which includes a sandy beach and general coastal views as well as a small group of people

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

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

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

CA $14
per traveller
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour
Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

CA $23
per traveller
Portland Smartphone Audio Tour: Self-Guided Drive
Ultimate Portland Self-Guided Driving GPS Audio Tour

Ultimate Portland Self-Guided Driving GPS Audio Tour

CA $23
per traveller
100% of travellers recommend
Ultimate Portland Self-Guided Driving GPS 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.

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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.