Title: Great Diamond Island Vacation Packages & Trips 2026 from CA $627 | Expedia.ca [Great Diamond Island Travel Guide](https://expedia.ca/Great-Diamond-Island.dx6342016)[Hotels in Great Diamond Island](https://expedia.ca/Great-Diamond-Island-Hotels.d6342016.Travel-Guide-Hotels)[Vacation Rentals in Great Diamond Island](https://expedia.ca/Great-Diamond-Island-Vacation-Rentals.d6342016.Travel-Guide-VacationRentals)[Flights to Great Diamond Island](https://expedia.ca/Cheap-Flights-To-Great-Diamond-Island.d6342016.Travel-Guide-Flights)[Great Diamond Island Car Rentals](https://expedia.ca/Car-Rentals-In-Great-Diamond-Island.d6342016.Car-Rental-Guide) ![](https://images.trvl-media.com/place/181420/3cfa4a35-2db7-47c5-b7aa-531fbc9a8da8.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Great Diamond Island Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by Robbie Martin - ## 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. ![Portland Harbor Hotel](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/83fe4590_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Portland Harbor Hotel Downtown Portland CA $627 per person Feb 20 - Feb 24 found 16 hours ago Roundtrip non-stop flight included Edmonton (YEG) to Portland (PWM) 9.2/10 Wonderful! (1,668 reviews) I had a Junior Suite and it was lovely. Bed was extremely comfortable and it was very quiet. I will say the breakfast is costly in my opinion but it was great. Reviewed on Jan 6, 2026 ![InnSeason Resorts The Falls at Ogunquit](https://images.trvl-media.com/lodging/2000000/1160000/1154500/1154484/bbe3272a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### InnSeason Resorts The Falls at Ogunquit CA $780 per person Feb 20 - Feb 25 found 16 hours ago Roundtrip non-stop flight included Edmonton (YEG) to Portland (PWM) 9.4/10 Exceptional! (356 reviews) Great clean and friendly place Love returning every year Reviewed on Jan 7, 2026 ![The McKernan Inn](https://images.trvl-media.com/lodging/106000000/105380000/105370700/105370688/f7ebd781_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The McKernan Inn CA $1,002 per person Mar 23 - Mar 27 found 19 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Portland (PWM) 9/10 Wonderful! (83 reviews) Gorgeous grounds and venue with a beautiful oceanfront view. Plenty of parking as part of SMCC campus. Short drive to downtown Portland and lots of stores around in South Portland. Very unique experience, would stay again without hesitation! Reviewed on Dec 27, 2025 ![AC Hotel Portland Downtown/Waterfront, ME](https://images.trvl-media.com/lodging/23000000/22520000/22514800/22514704/f9c45283_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### AC Hotel Portland Downtown/Waterfront, ME East Bayside CA $710 per person Feb 20 - Feb 25 found 16 hours ago Roundtrip non-stop flight included Edmonton (YEG) to Portland (PWM) 9.2/10 Wonderful! (1,001 reviews) Convenient, clean, nice people Reviewed on Jan 2, 2026 ![84 Main ](https://images.trvl-media.com/lodging/8000000/7810000/7805200/7805164/f78a93a3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 84 Main CA $650 per person Feb 20 - Feb 24 found 16 hours ago Roundtrip non-stop flight included Edmonton (YEG) to Portland (PWM) 10/10 Exceptional! (52 reviews) This property was absolutely beautiful and well maintained! Right in the heart of Kennebunk within walking distance to great restaurants!! Reviewed on Oct 26, 2025 ## Ready to book your vacation to Great Diamond Island? Choose your dates ## Great Diamond Island Hotel Deals ![Clarion Hotel Portland Airport ME](https://images.trvl-media.com/lodging/1000000/10000/7200/7171/b163ad24_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Clarion Hotel Portland Airport ME 1230 Congress St Portland ME Fully refundableReserve now, pay when you stay CA $108 CA $120 total Jan 11 - Jan 12 includes taxes & fees 7.8/10 Good! (1,316 reviews) The staff were great. Friendly and helpful! Loved the use of the shuttle into town Reviewed on Jan 2, 2026 [](https://expedia.ca/Hotel-Search?startDate=11%2F01%2F2026&endDate=12%2F01%2F2026&selected=7171&PinnedHotelID=7171&HadPinnedHotel=true®ionId=6342016) ![The Westin Portland Harborview](https://images.trvl-media.com/lodging/1000000/10000/6300/6273/67608060_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Westin Portland Harborview 157 High St Portland ME Fully refundableReserve now, pay when you stay CA $135 CA $150 total Jan 25 - Jan 26 includes taxes & fees 8.8/10 Excellent! (1,007 reviews) Wonderful as always. Comfortable beds, spacious rooms. Lovely, helpful staff Reviewed on Dec 29, 2025 [](https://expedia.ca/Hotel-Search?startDate=25%2F01%2F2026&endDate=26%2F01%2F2026&selected=6273&PinnedHotelID=6273&HadPinnedHotel=true®ionId=6342016) ![Portland Regency Hotel & Spa](https://images.trvl-media.com/lodging/1000000/930000/920100/920050/c8a0ec33_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Portland Regency Hotel & Spa 20 Milk Street Portland ME Fully refundableReserve now, pay when you stay CA $176 CA $194 total Jan 11 - Jan 12 includes taxes & fees 9.4/10 Exceptional! (1,567 reviews) Staff was great. Perfect location to explore the area. Reviewed on Jan 4, 2026 [](https://expedia.ca/Hotel-Search?startDate=11%2F01%2F2026&endDate=12%2F01%2F2026&selected=920050&PinnedHotelID=920050&HadPinnedHotel=true®ionId=6342016) [See all 2,272 properties in Great Diamond Island](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=09%2F01%2F2026&endDate=10%2F01%2F2026®ionId=6342016) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### Discover the most popular places to visit in Great Diamond Island ![State Theatre showing street scenes as well as an individual female](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/266000/266254-Portland-Maine.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 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. [](https://expedia.ca/State-Theatre-Downtown-Portland.d553248621532668181.Vacation-Attraction) ![Portland Museum of Art which includes interior views and art as well as a small group of people](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/267000/267551-South-Coast-Maine.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 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. [](https://expedia.ca/Portland-Museum-Of-Art-Downtown-Portland.d6077214.Vacation-Attraction) ![East End Beach which includes a sandy beach and general coastal views as well as a small group of people](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/268000/268075-East-End-Beach-Portland.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 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. [](https://expedia.ca/East-End-Beach-East-End.d6326357.Vacation-Attraction) ### What to do in Great Diamond Island ![Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour](https://mediaim.expedia.com/localexpert/44927495/42f8f2e5-289d-480a-a822-cc8751cc6b66.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour CA $14 per traveller [](https://expedia.ca/things-to-do/downtown-portland-coastal-vibe-and-old-mansions-with-in-add-audio-tour.a44927495.activity-details) ![Portland Self-Guided Driving Audio Tour](https://mediaim.expedia.com/localexpert/45719150/c5757d24-772a-4314-9a5b-385c37350ecc.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Portland Smartphone Audio Tour: Self-Guided Drive CA $21 per traveller [](https://expedia.ca/things-to-do/portland-smartphone-audio-tour-self-guided-drive.a45719150.activity-details) ![Ultimate Portland Self-Guided Driving GPS Audio Tour](https://mediaim.expedia.com/localexpert/44941422/00064774-1203-465f-8cee-e200125a2c6a.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Ultimate Portland Self-Guided Driving GPS Audio Tour CA $23 per traveller **100%** of travellers recommend [](https://expedia.ca/things-to-do/ultimate-portland-self-guided-driving-gps-audio-tour.a44941422.activity-details) [See all activities in Great Diamond Island](https://expedia.ca/things-to-do/search?rid=6342016) ## Frequently asked questions ### Can I cancel my flight booking to Great Diamond Island due to COVID-19? ### What's the best way to find cheap flights to Great Diamond Island that have flexible change policies? ### What are some of the general tips for travelers to Great Diamond Island during the COVID-19 outbreak? > - 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? ### How can I find cheap tickets to Great Diamond Island? ### How much is a flight to Great Diamond Island? ### What are the most popular airports to fly into in Great Diamond Island? ### When is the cheapest time to fly to Great Diamond Island? ### How much is a plane ticket to Great Diamond Island? ### Which airlines with flights to Great Diamond Island employ COVID-19 cleanliness policies? > - 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 - Lodging - Flights - Packages - Cars - Vacation Rental - Other - [Hotels near Casco Bay Lines Ferry Terminal ](https://www.expedia.ca/Casco-Bay-Lines-Ferry-Terminal-Hotels.0-l553248621533120972-0.Travel-Guide-Filter-Hotels) - 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[Dunegrass Golf Club ](https://www.expedia.ca/Dunegrass-Golf-Club-Old-Orchard-Beach.d6326332.Vacation-Attraction) - [East End Beach ](https://www.expedia.ca/East-End-Beach-East-End.d6326357.Vacation-Attraction) - [Freeport Vacations ](https://www.expedia.ca/Freeport.d180773.Destination-Travel-Guides) - [Great Island Vacations ](https://www.expedia.ca/Great-Island.d553248635976193455.Destination-Travel-Guides) - [Higgins Beach ](https://www.expedia.ca/Higgins-Beach-Maine.d6326755.Vacation-Attraction) - [Ll Bean Flagship Store ](https://www.expedia.ca/LL-Bean-Flagship-Store-Freeport.d6180409.Vacation-Attraction) - [Long Island Vacations ](https://www.expedia.ca/Long-Island.d6046209.Destination-Travel-Guides) - [Maine Mall ](https://www.expedia.ca/Maine-Mall-South-Portland.d6077232.Vacation-Attraction) - [Mclellan-Sweat Mansion ](https://www.expedia.ca/McLellan-Sweat-Mansion-Downtown-Portland.d6327527.Vacation-Attraction) - [Monkey Trunks Extreme Aerial Adventure Park ](https://www.expedia.ca/Monkey-Trunks-Extreme-Aerial-Adventure-Park-Saco.d6327529.Vacation-Attraction) - [Old Orchard Beach Pier ](https://www.expedia.ca/Old-Orchard-Beach-Pier-Old-Orchard-Beach.d553248625038645898.Vacation-Attraction) - [Old Orchard Beach Vacations ](https://www.expedia.ca/Old-Orchard-Beach.d9256.Destination-Travel-Guides) - [Palace Playland ](https://www.expedia.ca/Palace-Playland-Old-Orchard-Beach.d553248621532667539.Vacation-Attraction) - [Pine Point Beach ](https://www.expedia.ca/Pine-Point-Beach-Maine.d671870122573062144.Vacation-Attraction) - [Visit East Bayside ](https://www.expedia.ca/Portland-East-Bayside.dx553248635976473226) - [Portland Head Light ](https://www.expedia.ca/Portland-Head-Light-Cape-Elizabeth.d6077212.Vacation-Attraction) - [Portland Museum of Art ](https://www.expedia.ca/Portland-Museum-Of-Art-Downtown-Portland.d6077214.Vacation-Attraction) - [Visit Old Port ](https://www.expedia.ca/Portland-Old-Port.dx6172121) - [Portland Vacations ](https://www.expedia.ca/Portland.d181420.Destination-Travel-Guides) - [Visit Portland ](https://www.expedia.ca/Portland.dx181420) - [Scarborough Beach State Park ](https://www.expedia.ca/Scarborough-Beach-State-Park-Scarborough.d6327764.Vacation-Attraction) - [Scarborough Vacations ](https://www.expedia.ca/Scarborough.d6809.Destination-Travel-Guides) - [Shaw Park ](https://www.expedia.ca/Shaw-Park-Gorham.d553248633861906803.Vacation-Attraction) - [Visit Ferry Village ](https://www.expedia.ca/South-Portland-Ferry-Village.dx553248635976469773) - [South Portland Vacations ](https://www.expedia.ca/South-Portland.d6769.Destination-Travel-Guides) - [State Theatre ](https://www.expedia.ca/State-Theatre-Downtown-Portland.d553248621532668181.Vacation-Attraction) - [Westbrook Vacations ](https://www.expedia.ca/Westbrook.d56049.Destination-Travel-Guides) - [Windham Vacations ](https://www.expedia.ca/Windham.d10053.Destination-Travel-Guides) - [Car rental Portland ](https://www.expedia.ca/Car-Rentals-In-Portland.d181420.Car-Rental-Guide) - [Peaks Island Vacation Rentals ](https://www.expedia.ca/Peaks-Island-Vacation-Rentals.d6151240.Travel-Guide-VacationRentals) - [Things to do in Portland ](https://www.expedia.ca/Things-To-Do-In-Portland.d181420.Travel-Guide-Activities) \* Savings based on package bookings compared to the price of the same components booked separately. 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