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 $4,200 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.
Saco Bay Hotel

Saco Bay Hotel

2.5 out of 5
Price was CA $1,454, price is now CA $1,184 per person
CA $1,184
per person
Jun 27 - Jul 2
found 9 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Portland (PWM)
7.6/10 Good! (1,056 reviews)
Hotel and rooms were clean . We enjoyed the breakfast in the morning before heading out . Overall good short stay !

Reviewed on May 18, 2026

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was CA $3,663, price is now CA $2,616 per person
CA $2,616
per person
Aug 2 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,762 reviews)
The Portland Harbor Hotel was lovely and very convenient to the tourist area of Portland. The staff were fantastic - very friendly and eager to share recommendations for things to do and places to eat. The hotel restaurant was a great choice for breakfast! And we really enjoyed relaxing at the end of the day by the firepit with our craft cocktails from the bar! It was a very enjoyable stay!

Reviewed on May 22, 2026

River View Resort

River View Resort

2.5 out of 5
Price was CA $2,205, price is now CA $1,589 per person
CA $1,589
per person
Aug 2 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9/10 Wonderful! (324 reviews)
Clean room. Space for everyone, pool was nice, staff was friendly. Perfect for our last minute ski trip.

Reviewed on Apr 12, 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 $2,512, price is now CA $1,968 per person
CA $1,968
per person
Jun 27 - Jul 2
found 9 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Portland (PWM)
9.6/10 Exceptional! (307 reviews)
Beautiful hotel, wonderful location. My only note is that the bed and pillows were not as comfortable as I would expect from this kind of boutique hotel. Standard size pillows only, no king size pillows and no lumbar pillows, and a fairly hard mattress with a thin pad. The night before my stay, I stayed in a converted motel for 25% of the Docent’s price that had far superior bedding.

Reviewed on May 20, 2026

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Price was CA $3,084, price is now CA $2,499 per person
CA $2,499
per person
Jun 27 - Jul 2
found 9 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Portland (PWM)
9.8/10 Exceptional! (101 reviews)
Lovely suite! Comfy king bed, everything spotless, Great location. Would stay here again

Reviewed on Apr 23, 2026

Ready to book your vacation to Great Diamond Island?

 

Choose your dates

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 CA $256 per night from May 26 to May 27
CA $256
CA $336 total
May 26 - May 27
includes taxes & fees
9.4/10 Exceptional! (1,765 reviews)
"The New England decor was pleasant. The free snack station on each floor was great (fruit, yogurt, granola, pastries, trail mix bars, coffee, multiple tea flavors, cookies) are a nice edition. We avoided the destination/resort fee be having breakfast or cocktails each day. The outdoor fire pits were ..."

Reviewed on May 23, 2026

Portland Harbor Hotel
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $206 per night from May 26 to May 27
CA $206
CA $228 total
May 26 - May 27
includes taxes & fees
9.4/10 Exceptional! (1,646 reviews)
"We’ve stayed at this hotel 5 times now and have always enjoyed the historic charm and location. Check-in during this stay went smoothly, however we were disappointed when we arrived to find the toilet in our room was dirty. We also asked the front desk if the TVs allowed streaming services like Netflix ..."

Reviewed on May 20, 2026

Portland Regency Hotel & Spa
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 $247 per night from May 31 to Jun 1
CA $247
CA $311 total
May 31 - Jun 1
includes taxes & fees
9.4/10 Exceptional! (1,219 reviews)
"Clean room, nice location. Wish the tv was a smart tv, and found the $25/room sort of annoying since the restaurant on property was understaffed. But overall we enjoyed it."

Reviewed on May 21, 2026

Cambria Hotel Portland Downtown-Old Port
See all 2,383 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

Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

CA $21
per traveller
Portland Smartphone Audio Tour: Self-Guided Drive
Portland Explorer: Cultural/Historical & 3 Lighthouses Tour

Portland Explorer | Maine History, Culture, & 3 Lighthouses Tour

CA $124
per adult
100% of travellers recommend
Portland Explorer | Maine History, Culture, & 3 Lighthouses 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.

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.