Great Diamond Island Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Great Diamond Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

Casco Bay Hotel Portland Airport - Maine Mall, an Ascend Collection Hotel

3.5 out of 5
Price was CA $1,417, price is now CA $1,151 per person
CA $1,151
per person
Jul 10 - Jul 15
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
8.4/10 Very Good! (2,891 reviews)
Overall this was a good experience. The staff was friendly and the property was clean.

Reviewed on Apr 14, 2026

Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Price was CA $2,285, price is now CA $1,334 per person
CA $1,334
per person
Jul 10 - Jul 15
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9/10 Wonderful! (1,000 reviews)
The room was very clean!

Reviewed on Oct 31, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was CA $2,378, price is now CA $1,655 per person
CA $1,655
per person
Jul 10 - Jul 15
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9.2/10 Wonderful! (1,766 reviews)
Convenient location and well decorated with excellent dining facility. staff is charming.

Reviewed on Apr 16, 2026

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
Price was CA $2,240, price is now CA $1,791 per person
CA $1,791
per person
Jul 10 - Jul 15
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (1,619 reviews)
Pet friendly and centrally located. A very nice getaway weekend.

Reviewed on Apr 13, 2026

The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Downtown Portland
Price was CA $3,043, price is now CA $2,488 per person
CA $2,488
per person
Jul 10 - Jul 15
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (291 reviews)
We thoroughly enjoyed our 4-night stay at The Docent's Collection. The staff was outstanding (shout-out to Spencer and Sarah!). The apartment we stayed in was roomy, impeccably clean, and well-furnished. We had everything we needed for our stay. Security was great, parking was easy, and right next to a police parking lot, so very secure. We look forward to staying here again!

Reviewed on Apr 15, 2026

Ready to book your vacation to Great Diamond Island?

 

Choose your dates

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 $204 per night from Apr 19 to Apr 20
CA $204
CA $226 total
Apr 19 - Apr 20
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
The staff should tell the gusts that breakfast need voucher even the gusts already paid the breakfast.

Reviewed on Apr 15, 2026

The Westin Portland Harborview
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 $168 per night from Apr 26 to Apr 27
CA $168
CA $223 total
Apr 26 - Apr 27
includes taxes & fees
9.4/10 Exceptional! (1,192 reviews)
All was perfect, staff friendly and professional, breakfast great, room clean.

Reviewed on Apr 16, 2026

Cambria Hotel Portland Downtown-Old Port
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 $139 per night from Apr 26 to Apr 27
CA $139
CA $206 total
Apr 26 - Apr 27
includes taxes & fees
9.2/10 Wonderful! (1,773 reviews)
Convenient location and well decorated with excellent dining facility. staff is charming.

Reviewed on Apr 16, 2026

Portland Harbor Hotel
See all 2,361 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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

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 $13
per traveller
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour
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
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.

Explore a world of travel with Expedia

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