Title: TOP Historic Hotels in Great Diamond Island, ME for 2026 | Expedia.co.uk [Great Diamond Island Travel Guide](https://expedia.co.uk/Great-Diamond-Island.dx6342016)[Hotels in Great Diamond Island](https://expedia.co.uk/Great-Diamond-Island-Hotels.d6342016.Travel-Guide-Hotels)[Holiday Rentals in Great Diamond Island](https://expedia.co.uk/Great-Diamond-Island-Holiday-Rentals.d6342016.Travel-Guide-HolidayRentals)[Flights to Great Diamond Island](https://expedia.co.uk/Cheap-Flights-To-Great-Diamond-Island.d6342016.Travel-Guide-Flights)[Great Diamond Island Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Great-Diamond-Island.d6342016.Car-Hire-Guide)[Great Diamond Island Holidays](https://expedia.co.uk/Great-Diamond-Island.d6342016.Holidays-City-Breaks) ![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) # Search Historic Hotels in Great Diamond Island - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](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 Historic Hotels Tonight [15 Dec - 16 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=6342016&startDate=2025-12-15&endDate=2025-12-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [16 Dec - 17 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=6342016&startDate=2025-12-16&endDate=2025-12-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [19 Dec - 21 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=6342016&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [26 Dec - 28 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=6342016&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Great Diamond Island historic hotels ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/930000/920100/920050/c8a0ec33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Gym](https://images.trvl-media.com/lodging/1000000/930000/920100/920050/e38717ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Room | In-room safe, individually furnished, iron/ironing board](https://images.trvl-media.com/lodging/1000000/930000/920100/920050/2cd1b596.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/930000/920100/920050/917fa099.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Portland Regency Hotel & Spa [](https://www.expedia.co.uk/Portland-Hotels-Portland-Regency-Hotel-Spa.h920050.Hotel-Information) Downtown Portland 9.4/10 Exceptional (1551) "Yes, excellent service and we really enjoyed our stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bruce £104 includes taxes & fees 15 Jan - 16 Jan 2026 [](https://www.expedia.co.uk/Portland-Hotels-Portland-Regency-Hotel-Spa.h920050.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, pool 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.co.uk/Portland-Hotels-Holiday-Inn-Portland-By-The-Bay.h11991.Hotel-Information) Downtown Portland 8.8/10 Excellent (1432) "Every thing was perfect, service, accomodations, and friendly staff!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael £65 includes taxes & fees 22 Dec - 23 Dec [](https://www.expedia.co.uk/Portland-Hotels-Holiday-Inn-Portland-By-The-Bay.h11991.Hotel-Information) ![Royal Suite, 1 Bedroom | Frette Italian sheets, hypo-allergenic bedding, pillow-top beds](https://images.trvl-media.com/lodging/11000000/10650000/10645800/10645706/fe8abaa6.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) ![Room, 2 Double Beds | Frette Italian sheets, hypo-allergenic bedding, pillow-top beds](https://images.trvl-media.com/lodging/11000000/10650000/10645800/10645706/4099b709.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges](https://images.trvl-media.com/lodging/11000000/10650000/10645800/10645706/a5f194ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Press Hotel, Marriott Autograph Collection [](https://www.expedia.co.uk/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 £129 includes taxes & fees 22 Dec - 23 Dec [](https://www.expedia.co.uk/Portland-Hotels-The-Press-Hotel.h10645706.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1510000/1507200/1507122/25e0b609.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/2000000/1510000/1507200/1507122/051c3176.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1510000/1507200/1507122/47cc93e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually decorated, individually furnished, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1510000/1507200/1507122/49180f74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Old Orchard Beach Inn [](https://www.expedia.co.uk/Portland-Hotels-Old-Orchard-Beach-Inn.h1507122.Hotel-Information) Old Orchard Beach 8.2/10 Very good (1001) "A beautiful place to stay!!! First time at a B&B and it did not disappoint." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristian [](https://www.expedia.co.uk/Portland-Hotels-Old-Orchard-Beach-Inn.h1507122.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/2000000/1490000/1489300/1489274/5d783f80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/2000000/1490000/1489300/1489274/c17fb587.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1490000/1489300/1489274/e5c17fb8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 Queen Bed, Jetted Tub | Premium bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/2000000/1490000/1489300/1489274/4a1ea5b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The James Place Inn B&B [](https://www.expedia.co.uk/Portland-Hotels-The-James-Place-Inn-Bed-And-Breakfast.h1489274.Hotel-Information) Freeport 10/10 Exceptional (182) "Wish we could have stayed longer. It has the ambiance of an older inn but the rooms are very clean and well maintained. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melissa £178 includes taxes & fees 27 Dec - 28 Dec [](https://www.expedia.co.uk/Portland-Hotels-The-James-Place-Inn-Bed-And-Breakfast.h1489274.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/33000000/32440000/32432100/32432059/91a3f768.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/33000000/32440000/32432100/32432059/w1917h1645x3y0-1a82cf6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/33000000/32440000/32432100/32432059/310f34f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/33000000/32440000/32432100/32432059/4fe2dda9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Adorable Portland getaway on the Eastern Promenade [](https://www.expedia.co.uk/Portland-Hotels-Adorable-Portland-Getaway-On-The-Eastern-Promenade.h32432059.Hotel-Information) Munjoy Hill 9.6/10 Exceptional (127) "Very convenient location. Comfortable accommodation! I would stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cynthia W. £124 includes taxes & fees 17 Dec - 18 Dec [](https://www.expedia.co.uk/Portland-Hotels-Adorable-Portland-Getaway-On-The-Eastern-Promenade.h32432059.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/35000000/34430000/34429200/34429189/05e36322.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/35000000/34430000/34429200/34429189/8b6a6a53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34430000/34429200/34429189/5c9e0f77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34430000/34429200/34429189/a8df7e60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### City Amenities, Casco Bay Sunrises and Natural Beauty [](https://www.expedia.co.uk/Portland-Hotels-City-Amenities.h34429189.Hotel-Information) East Deering 9.8/10 Exceptional (122) "The house was clean and homey…everything was well stocked and supplies were even there for our pet…great access to the highway…the views were beautiful…would definitely recommend! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle M. £198 includes taxes & fees 17 Dec - 18 Dec [](https://www.expedia.co.uk/Portland-Hotels-City-Amenities.h34429189.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/33000000/32670000/32668900/32668873/w1917h1645x3y0-c1000dba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/33000000/32670000/32668900/32668873/31da49e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/33000000/32670000/32668900/32668873/w1920h1432x0y17-48abbb9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32670000/32668900/32668873/d260b69a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Glorious getaway on Portland's Eastern Promenade. [](https://www.expedia.co.uk/Portland-Hotels-Glorious-Getaway-On-Portlands-Eastern-Promenade.h32668873.Hotel-Information) Munjoy Hill 9.8/10 Exceptional (171) "Great location, clean and cute." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Erin M. £179 includes taxes & fees 17 Dec - 18 Dec [](https://www.expedia.co.uk/Portland-Hotels-Glorious-Getaway-On-Portlands-Eastern-Promenade.h32668873.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/99000000/98550000/98542900/98542897/d8e1ac8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/99000000/98550000/98542900/98542897/4cacdbc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/99000000/98550000/98542900/98542897/eec91961.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/99000000/98550000/98542900/98542897/1f474b76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport [](https://www.expedia.co.uk/Freeport-Hotels-Beautiful-Stay-In-Downtown-Freeport.h98542897.Hotel-Information) Freeport 10/10 Exceptional (4) "We had a wonderful time in Freeport, getting some Christmas season shopping in and bring our 4 year old to the Sparkle weekend festivities. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David H. [](https://www.expedia.co.uk/Freeport-Hotels-Beautiful-Stay-In-Downtown-Freeport.h98542897.Hotel-Information) ![Smart TV](https://images.trvl-media.com/lodging/70000000/69570000/69568100/69568092/8bfdb3b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/70000000/69570000/69568100/69568092/1d3cb344.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/70000000/69570000/69568100/69568092/519ceff9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/70000000/69570000/69568100/69568092/30c8c437.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful 1st Floor Apartment & Amazing Shower [](https://www.expedia.co.uk/Portland-Hotels-Beautiful-1st-Floor-Apartment-Amazing-Shower.h69568092.Hotel-Information) Parkside 9.0/10 Wonderful (26) "This was a clean and good location for our stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jocelyn R. £113 includes taxes & fees 17 Dec - 18 Dec [](https://www.expedia.co.uk/Portland-Hotels-Beautiful-1st-Floor-Apartment-Amazing-Shower.h69568092.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.co.uk/Hotel-Search?startDate=2025-12-30&endDate=2025-12-31®ionId=6342016&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Great Diamond Island Hotel Reviews ![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 "Clean and comfortable room, nice staff" [](https://expedia.co.uk/Portland-Hotels-DoubleTree-By-Hilton-Hotel-Portland.h8166.Hotel-Information) ![Portland Harbor Hotel](https://images.trvl-media.com/lodging/1000000/900000/898700/898621/83fe4590_y.jpg) ### Portland Harbor Hotel 10/10 Excellent "Lovely stay in a beautiful room, appreciated the upgrade. Easy walk to downtown activities. " [](https://expedia.co.uk/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 "yes" [](https://expedia.co.uk/Portland-Hotels-Clarion-Hotel-Portland.h7171.Hotel-Information) ![Hyatt Place Portland Downtown - Old Port Square](https://images.trvl-media.com/lodging/8000000/7490000/7488200/7488159/b4e33349_y.jpg) ### Hyatt Place Portland Downtown - Old Port Square 10/10 Excellent "coean and stylish room. Staff were helpful and friendly. Great location." [](https://expedia.co.uk/Portland-Hotels-Hyatt-Place-Portland-Old-Port.h7488159.Hotel-Information) ![Hampton Inn Portland Downtown - Waterfront](https://images.trvl-media.com/lodging/5000000/4490000/4480300/4480291/1dc67cbc_y.jpg) ### Hampton Inn Portland Downtown - Waterfront 10/10 Excellent "clean room, digital key wonderful, good breakfast selection, staff very accommodating. Pool water very, very cloudy (negative)" [](https://expedia.co.uk/Portland-Hotels-Hampton-Inn-Portland-Downtown-Waterfront.h4480291.Hotel-Information) ![Holiday Inn Portland-By the Bay by IHG](https://images.trvl-media.com/lodging/1000000/20000/12000/11991/e922ee9f_y.jpg) ### Holiday Inn Portland-By the Bay by IHG 10/10 Excellent "Very nice place" [](https://expedia.co.uk/Portland-Hotels-Holiday-Inn-Portland-By-The-Bay.h11991.Hotel-Information) ![Fireside Inn & Suites Portland](https://images.trvl-media.com/lodging/1000000/10000/9900/9842/bc09b846_y.jpg) ### Fireside Inn & Suites Portland 10/10 Excellent "The room was clean" [](https://expedia.co.uk/Portland-Hotels-Fireside-Inn-Suites.h9842.Hotel-Information) ![Portland Regency Hotel & Spa](https://images.trvl-media.com/lodging/1000000/930000/920100/920050/c8a0ec33_y.jpg) ### Portland Regency Hotel & Spa 10/10 Excellent "Everything " [](https://expedia.co.uk/Portland-Hotels-Portland-Regency-Hotel-Spa.h920050.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 "Room was spotless and the staff was extremely friendly and knowledgeable! Would definitely stay here again!" 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