Title: Book the Best HISTORIC Hotels in Great Diamond Island in 2025 | 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) ![](https://mediaim.expedia.com/destination/2/f025022e6f41a1444f171eeef26e2d2c.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Robbie Martin # Find Historic 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 Historic Hotels Tonight [Oct 24 - Oct 25](https://www.expedia.ca/Hotel-Search?regionId=6342016&startDate=2025-10-24&endDate=2025-10-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 25 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6342016&startDate=2025-10-25&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6342016&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6342016&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top 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) ![Lobby](https://images.trvl-media.com/lodging/1000000/930000/920100/920050/917fa099.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/930000/920100/920050/21df5bb0.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) ### Portland Regency Hotel & Spa Downtown Portland 9.4/10 Exceptional (1486) "staff was amazing, room was spotless and comfy, easy to walk downtown" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christine CA $189 CA $210 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/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) ![Hypo-allergenic bedding, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/1000000/20000/12000/11991/e637b60c.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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/12000/11991/0fe73756.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Portland-By the Bay by IHG Downtown Portland 9.0/10 Wonderful (1379) "Easy check in, walkable to so many places " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deborah CA $109 CA $121 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Portland-Hotels-Holiday-Inn-Portland-By-The-Bay.h11991.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) ![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](https://images.trvl-media.com/lodging/11000000/10650000/10645800/10645706/4099b709.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Press Hotel, Marriott Autograph Collection Downtown Portland 9.4/10 Exceptional (1001) "The Press Hotel nails the “old newsroom turned boutique” thing without the cigarette smoke or deadlines. Sharp rooms, great staff, and enough personality to make every chain hotel feel like a press release." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew CA $231 CA $255 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Portland-Hotels-The-Press-Hotel.h10645706.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/19000000/18670000/18669400/18669303/b1c4f654.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/18670000/18669400/18669303/e646aca0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Signature Room, 1 Queen Bed | Interior](https://images.trvl-media.com/lodging/19000000/18670000/18669400/18669303/18f26d53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/18670000/18669400/18669303/5f8ff532.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Francis Parkside 9.4/10 Exceptional (361) "It was so charming and the beds were amazing." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Danny CA $159 CA $215 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Portland-Hotels-The-Francis.h18669303.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/28000000/27480000/27476300/27476270/80c2d1cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/28000000/27480000/27476300/27476270/d87ce049.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/28000000/27480000/27476300/27476270/18ba7a8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/28000000/27480000/27476300/27476270/10493eba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Centerview cottage Harpswell 9.6/10 Exceptional (58) "Tip Top!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Virginia M. CA $337 CA $575 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Harpswell-Hotels-Centerview-Cottage.h27476270.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1510000/1507200/1507122/355a3aa3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Old Orchard Beach Inn Old Orchard Beach 8.2/10 Very good (1002) "Clean and very quaint room. Would stay again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa CA $161 CA $176 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Portland-Hotels-Old-Orchard-Beach-Inn.h1507122.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) ![1 bedroom, hypo-allergenic bedding, in-room safe, blackout drapes](https://images.trvl-media.com/lodging/96000000/95700000/95697200/95697174/6dd3e447.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) ![Business Room](https://images.trvl-media.com/lodging/96000000/95700000/95697200/95697174/b7e27ec1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Longfellow Hotel Parkside 9.6/10 Exceptional (120) "Fabulous hotel, wonderful staff with a fabulous cafe attached for breakfast. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer CA $162 CA $233 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Portland-Hotels-Longfellow-Hotel.h95697174.Hotel-Information) ![Smart TV, books](https://images.trvl-media.com/lodging/60000000/59660000/59656700/59656609/57552257.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/60000000/59660000/59656700/59656609/bc289767.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/60000000/59660000/59656700/59656609/3f754004.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/60000000/59660000/59656700/59656609/44b25a9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Brand New Downtown 2BR on Noble Next to Bowdoin(Safe&Sound) Brunswick 9.8/10 Exceptional (27) "Great location and just the place we needed to explore Brunswick. The A/C units were welcome in the midst of the wave of warm weather! The landlord was very responsive. We’d stay there again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dana B. CA $217 CA $524 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Brunswick-Hotels-Brand-New-Downtown-2BR-On-Noble-Next-To-Bowdoin.h59656609.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) ![Traditional Room, 1 Bedroom, Bathtub](https://images.trvl-media.com/lodging/2000000/1490000/1489300/1489274/20306c1b.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) ![Deluxe Room, 1 Queen Bed, Jetted Tub](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 Freeport 10/10 Exceptional (181) "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 CA $365 CA $398 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Portland-Hotels-The-James-Place-Inn-Bed-And-Breakfast.h1489274.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/72000000/71810000/71801700/71801603/0db21c43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/72000000/71810000/71801700/71801603/6fc2838f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/72000000/71810000/71801700/71801603/69545df6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71810000/71801700/71801603/c912865d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Private Apartment, minutes from LLBean! Freeport 10/10 Exceptional (14) "We had a lovely stay at this property. Comfortable bed, beautiful view, enjoyed using the sauna, would stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emily Jeanne B. CA $263 CA $421 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Freeport-Hotels-Waterfront-Private-Apartment.h71801603.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=2025-11-07&endDate=2025-11-08®ionId=6342016&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Great Diamond Island Hotel Reviews ![Germaine Inn South Portland](//images.trvl-media.com/lodging/1000000/30000/23800/23779/b95e6193_y.jpg) ### Germaine Inn South Portland 10/10 Excellent "Yes nice staff" [](https://expedia.ca/South-Portland-Hotels-Germaine-Inn-South-Portland.h23779.Hotel-Information) ![Comfort Inn Airport](//images.trvl-media.com/lodging/1000000/30000/27100/27041/e9231d1b_y.jpg) ### Comfort Inn Airport 10/10 Excellent "Room was clean and very well maintained. Breakfast was tasty. " [](https://expedia.ca/Portland-Hotels-Comfort-Inn-Airport.h27041.Hotel-Information) ![Fireside Inn & Suites Portland](//images.trvl-media.com/lodging/1000000/10000/9900/9842/bc09b846_y.jpg) ### Fireside Inn & Suites Portland 10/10 Excellent "Everything was convenient. " [](https://expedia.ca/Portland-Hotels-Fireside-Inn-Suites.h9842.Hotel-Information) ![Portland Harbor Hotel](//images.trvl-media.com/lodging/1000000/900000/898700/898621/83fe4590_y.jpg) ### Portland Harbor Hotel 10/10 Excellent "Very clean and walkable to most of the city." [](https://expedia.ca/Portland-Hotels-Portland-Harbor-Hotel.h898621.Hotel-Information) ![Clarion Hotel Portland](//images.trvl-media.com/lodging/1000000/10000/7200/7171/b163ad24_y.jpg) ### Clarion Hotel Portland 10/10 Excellent "The staff were super friendly. The breakfast was good " [](https://expedia.ca/Portland-Hotels-Clarion-Hotel-Portland.h7171.Hotel-Information) ![Portland Regency Hotel & Spa](//images.trvl-media.com/lodging/1000000/930000/920100/920050/c8a0ec33_y.jpg) ### Portland Regency Hotel & Spa 10/10 Excellent "The airport shuttle was professio" [](https://expedia.ca/Portland-Hotels-Portland-Regency-Hotel-Spa.h920050.Hotel-Information) ![Hyatt Place Portland Downtown - Old Port Square](//images.trvl-media.com/lodging/8000000/7490000/7488200/7488159/b4e33349_y.jpg) ### Hyatt Place Portland Downtown - Old Port Square 10/10 Excellent "Was a great location. We had an amazing view of the harbor from our room." [](https://expedia.ca/Portland-Hotels-Hyatt-Place-Portland-Old-Port.h7488159.Hotel-Information) ![Hampton Inn Portland Downtown - Waterfront](//images.trvl-media.com/lodging/5000000/4490000/4480300/4480291/1dc67cbc_y.jpg) ### Hampton Inn Portland Downtown - Waterfront 10/10 Excellent "Great stay! Clean rooms, pleasant and helpful staff, great food and variety in breakfast offerings. Great location within walkable distance from shopping, restaurants and activities around town. Highly recommend!" [](https://expedia.ca/Portland-Hotels-Hampton-Inn-Portland-Downtown-Waterfront.h4480291.Hotel-Information) ![Holiday Inn Portland-By the Bay by IHG](//images.trvl-media.com/lodging/1000000/20000/12000/11991/e922ee9f_y.jpg) ### Holiday Inn Portland-By the Bay by IHG 10/10 Excellent "Great location. Loved ocean view. 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