Title: Book the Best Great Diamond Island LUXURY Hotels - Upscale Hotels in Great Diamond Island, ME | 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)[Great Diamond Island Vacation Packages](https://expedia.ca/Great-Diamond-Island.d6342016.Destination-Travel-Guides) ![Summer on Casco Bay](https://images.trvl-media.com/place/6342016/fbb7e9ac-5d97-4416-ad7f-d1a6bdfac217.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find luxury hotels in Great Diamond Island, ME - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Great Diamond Island Luxury Hotels Tonight [Dec 29 - Dec 30](https://www.expedia.ca/Hotel-Search?regionId=6342016&startDate=2025-12-29&endDate=2025-12-30&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Dec 30 - Dec 31](https://www.expedia.ca/Hotel-Search?regionId=6342016&startDate=2025-12-30&endDate=2025-12-31&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) This weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6342016&startDate=2026-01-02&endDate=2026-01-04&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=6342016&startDate=2026-01-09&endDate=2026-01-11&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Our top choices for Great Diamond Island luxury hotels ![On the beach, fishing](https://images.trvl-media.com/lodging/2000000/1550000/1542800/1542725/d0fca35d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1550000/1542800/1542725/86bdeae0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/2000000/1550000/1542800/1542725/ceaf2fc9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's activities](https://images.trvl-media.com/lodging/2000000/1550000/1542800/1542725/a8100548.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn By The Sea [](https://www.expedia.ca/Portland-Hotels-Inn-By-The-Sea.h1542725.Hotel-Information) Cape Elizabeth 9.4/10 Exceptional (294) "Room was ready early friendly staff and room is better than expected " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeff [](https://www.expedia.ca/Portland-Hotels-Inn-By-The-Sea.h1542725.Hotel-Information) ![Premium bedding, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/83fe4590.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/w7354h4909x8y4-ca190742.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/w7357h4908x4y4-d5ff64f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/e9f78f3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Portland Harbor Hotel [](https://www.expedia.ca/Portland-Hotels-Portland-Harbor-Hotel.h898621.Hotel-Information) Downtown Portland 9.2/10 Wonderful (1730) "Great hotel in the perfect location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Samantha CA $151 CA $220 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Portland-Hotels-Portland-Harbor-Hotel.h898621.Hotel-Information) ![Royal Suite, 1 Bedroom](https://images.trvl-media.com/lodging/11000000/10650000/10645800/10645706/fe8abaa6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom | Bar (on property)](https://images.trvl-media.com/lodging/11000000/10650000/10645800/10645706/aa49ec5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Double Beds](https://images.trvl-media.com/lodging/11000000/10650000/10645800/10645706/4099b709.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/11000000/10650000/10645800/10645706/a6526c5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Press Hotel, Marriott Autograph Collection [](https://www.expedia.ca/Portland-Hotels-The-Press-Hotel.h10645706.Hotel-Information) Downtown Portland 9.4/10 Exceptional (1001) "Beautiful hotel, good & convenient restaurant and very short walk to Merrill Auditorium" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) PETER CA $214 CA $237 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Portland-Hotels-The-Press-Hotel.h10645706.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/1000000/10000/6300/6273/67608060.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/6300/6273/cb70d528.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/6300/6273/6645ae1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Rooftop bar, ocean views, open select days](https://images.trvl-media.com/lodging/1000000/10000/6300/6273/3136b7c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Westin Portland Harborview [](https://www.expedia.ca/Portland-Hotels-The-Westin-Portland-Harborview.h6273.Hotel-Information) Downtown Portland 8.8/10 Excellent (1005) "Spotless rooms, very roomy bathrooms, great staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kerrie CA $122 CA $135 total includes taxes & fees Jan 26 - Jan 27, 2026 [](https://www.expedia.ca/Portland-Hotels-The-Westin-Portland-Harborview.h6273.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/1000000/130000/126800/126758/2f62fb53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/1000000/130000/126800/126758/f26861cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pemaquid Point Room](https://images.trvl-media.com/lodging/1000000/130000/126800/126758/7c9e969a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/1000000/130000/126800/126758/ce6ea468.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Brewster House Bed & Breakfast [](https://www.expedia.ca/Portland-Hotels-Brewster-House-Bed-Breakfast.h126758.Hotel-Information) Freeport 9.8/10 Exceptional (114) "The food was wonderful and the hospitality was great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Olivia CA $212 CA $231 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Portland-Hotels-Brewster-House-Bed-Breakfast.h126758.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/10000/8200/8166/33bb60f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/8200/8166/41cba30c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/8200/8166/385a7714.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/8200/8166/6983fdb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### DoubleTree by Hilton Hotel Portland [](https://www.expedia.ca/Portland-Hotels-DoubleTree-By-Hilton-Hotel-Portland.h8166.Hotel-Information) South Portland 8.0/10 Very good (1326) "Very nice, fun pool, lovely staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sara CA $91 CA $99 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Portland-Hotels-DoubleTree-By-Hilton-Hotel-Portland.h8166.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/65000000/64480000/64474900/64474828/419cdab1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/65000000/64480000/64474900/64474828/a12adc1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/65000000/64480000/64474900/64474828/5cbd2b9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/65000000/64480000/64474900/64474828/32dbbc33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Canopy by Hilton Portland Waterfront [](https://www.expedia.ca/Portland-Hotels-Canopy-By-Hilton-Portland-Waterfront.h64474828.Hotel-Information) Downtown Portland 9.4/10 Exceptional (1005) "Clean, modern, comfortable rooms. Loved the rainfall shower. Excellent location in Portland Old Port near the waterfront." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah CA $167 CA $185 total includes taxes & fees Jan 19 - Jan 20, 2026 [](https://www.expedia.ca/Portland-Hotels-Canopy-By-Hilton-Portland-Waterfront.h64474828.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12000/11991/e922ee9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/12000/11991/73d7ad54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/20000/12000/11991/a27c6785.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, open 6:00 AM to 11:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/12000/11991/3150dd05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Portland-By the Bay by IHG [](https://www.expedia.ca/Portland-Hotels-Holiday-Inn-Portland-By-The-Bay.h11991.Hotel-Information) Downtown Portland 9.0/10 Wonderful (1445) "Excellent, clean, and the breakfast was great. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daihanny CA $107 CA $118 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Portland-Hotels-Holiday-Inn-Portland-By-The-Bay.h11991.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/96000000/95700000/95697200/95697174/73070e99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, in-room safe, blackout drapes, soundproofing](https://images.trvl-media.com/lodging/96000000/95700000/95697200/95697174/6dd3e447.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, in-room safe, blackout drapes, soundproofing](https://images.trvl-media.com/lodging/96000000/95700000/95697200/95697174/2e5de67c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business Room](https://images.trvl-media.com/lodging/96000000/95700000/95697200/95697174/cafac0c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Longfellow Hotel [](https://www.expedia.ca/Portland-Hotels-Longfellow-Hotel.h95697174.Hotel-Information) Parkside 9.6/10 Exceptional (140) "Best hotel ever!! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Heather CA $159 CA $228 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Portland-Hotels-Longfellow-Hotel.h95697174.Hotel-Information) ![Breakfast and dinner served, American cuisine](https://images.trvl-media.com/lodging/1000000/20000/12000/11961/c3c24612.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast and dinner served, American cuisine](https://images.trvl-media.com/lodging/1000000/20000/12000/11961/2db0386a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast and dinner served, American cuisine](https://images.trvl-media.com/lodging/1000000/20000/12000/11961/0882fecd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/12000/11961/4df81d59.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Portland Sheraton at Sable Oaks [](https://www.expedia.ca/Portland-Hotels-Portland-Sheraton-At-Sable-Oaks.h11961.Hotel-Information) South Portland 8.4/10 Very good (1003) "Very clean and extremely courteous staff. We like the restaurant. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard CA $163 CA $177 total includes taxes & fees Jan 18 - Jan 19, 2026 [](https://www.expedia.ca/Portland-Hotels-Portland-Sheraton-At-Sable-Oaks.h11961.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-01-13&endDate=2026-01-14®ionId=6342016&adults=2&sort=LUXURY&star=40,50&openPlayBack=true) ## Top Great Diamond Island Hotel Reviews ![Portland Regency Hotel & Spa](https://images.trvl-media.com/lodging/1000000/930000/920100/920050/c8a0ec33_y.jpg) ### Portland Regency Hotel & Spa 10/10 Excellent "Perfect location- lovely little hotel bar, nice room - friendly staff " [](https://expedia.ca/Portland-Hotels-Portland-Regency-Hotel-Spa.h920050.Hotel-Information) ![Portland Harbor Hotel](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/83fe4590_y.jpg) ### Portland Harbor Hotel 10/10 Excellent "Gorgeous hotel. Excellent location. Comfortable bed and pillows. Great shower! Can’t wait to go back again. " [](https://expedia.ca/Portland-Hotels-Portland-Harbor-Hotel.h898621.Hotel-Information) ![Clarion Hotel Portland Airport ME](https://images.trvl-media.com/lodging/1000000/10000/7200/7171/b163ad24_y.jpg) ### Clarion Hotel Portland Airport ME 10/10 Excellent "The airport shuttle was very convenient and appreciated on an early and snowy Christmas Eve morning. Night and morning desk staff were very helpful and friendly. " [](https://expedia.ca/Portland-Hotels-Clarion-Hotel-Portland.h7171.Hotel-Information) ![Embassy Suites by Hilton Portland Maine](https://images.trvl-media.com/lodging/1000000/20000/14800/14751/cbc24127_y.jpg) ### Embassy Suites by Hilton Portland Maine 10/10 Excellent "Convenient location with great breakfast" [](https://expedia.ca/Portland-Hotels-Embassy-Suites-By-Hilton-Portland-Maine.h14751.Hotel-Information) ![Long Creek Hotel by IHG](https://images.trvl-media.com/lodging/1000000/30000/24300/24280/f3b41288_y.jpg) ### Long Creek Hotel by IHG 10/10 Excellent "Everything about my stay at the long creek hotel was beyond my expectations! The friendliest staff I have ever had the pleasure of meeting! Definitely one of my new favorite local hotel getaways! " [](https://expedia.ca/Portland-Hotels-Hampton-Inn-Portland-Airport.h24280.Hotel-Information) ![DoubleTree by Hilton Hotel Portland](https://images.trvl-media.com/lodging/1000000/10000/8200/8166/33bb60f2_y.jpg) ### DoubleTree by Hilton Hotel Portland 10/10 Excellent "Very clean and cozy rooms, staff goes above and beyond to make you feel welcome and safe. Great coordination with Portland Jetport, and made me feel totally safe and reassured when snow ban was in effect for travel. Defiantly would return even if I’m not waiting for a flight! " [](https://expedia.ca/Portland-Hotels-DoubleTree-By-Hilton-Hotel-Portland.h8166.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Portland DT/Maine Med](https://images.trvl-media.com/lodging/1000000/30000/23500/23500/8325dcb5_y.jpg) ### La Quinta Inn & Suites by Wyndham Portland DT/Maine Med 10/10 Excellent "Easy to navigate. Clean. " [](https://expedia.ca/Portland-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Portland.h23500.Hotel-Information) ![Comfort Inn South Portland Airport](https://images.trvl-media.com/lodging/1000000/30000/27100/27041/e9231d1b_y.jpg) ### Comfort Inn South Portland Airport 10/10 Excellent "Clean room and friendly staff" [](https://expedia.ca/Portland-Hotels-Comfort-Inn-Airport.h27041.Hotel-Information) ![The Westin Portland Harborview](https://images.trvl-media.com/lodging/1000000/10000/6300/6273/67608060_y.jpg) ### The Westin Portland Harborview 10/10 Excellent "Staff was so friendly and had great dining recommendations. Room was super clean. Hotel was quiet and located in a perfect spot around the corner from the comedy show we went to see. Everything was so nice and good luck to the ginger bread house decoration competitors! We hope our choice wins!" 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