Title: Book the Best HISTORIC Hotels in Oakland in 2025 | Expedia.ca [Hotels in Oakland](https://expedia.ca/Oakland-Hotels.d9160.Travel-Guide-Hotels)[Vacation Rentals in Oakland](https://expedia.ca/Oakland-Vacation-Rentals.d9160.Travel-Guide-VacationRentals)[Oakland Car Rentals](https://expedia.ca/Car-Rentals-In-Oakland.d9160.Car-Rental-Guide)[Oakland Vacation Packages](https://expedia.ca/Oakland.d9160.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/6688cb44f390170dde19d3839b293328.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by KM Moore # Find Historic Hotels in Oakland, MD from CA $289 ![](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 Oakland Historic Hotels Tonight [Oct 15 - Oct 16](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-10-15&endDate=2025-10-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 16 - Oct 17](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-10-16&endDate=2025-10-17&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Oakland Historic Hotels ![Exterior](https://images.trvl-media.com/lodging/33000000/32820000/32818400/32818307/b818e0b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/33000000/32820000/32818400/32818307/a17f09c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/33000000/32820000/32818400/32818307/068471bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, books](https://images.trvl-media.com/lodging/33000000/32820000/32818400/32818307/e90d2cd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Butterfly Suite-Enchanted Elegance near DCL/Wisp! Fireplace! Meadow/Forest View! Accident 10/10 Exceptional (86) "Nice for a short stay! Super cute little area for our little family ! Would definitely go back ! " CA $119 CA $289 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Cumberland-Hotels-Enchanted-Elegance-Near-Deep-Creek-Lake-Wisp-Fireplace-Meadow-Forest-View.h32818307.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/50000000/49190000/49184200/49184146/cd4bfe55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/50000000/49190000/49184200/49184146/b5edd8d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, a heated pool](https://images.trvl-media.com/lodging/50000000/49190000/49184200/49184146/a23eb890.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/50000000/49190000/49184200/49184146/176bea50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Board Room-Enchanted Table Meadow. Near Deep Creek Lake & Wisp! Forest View! Accident 9.6/10 Exceptional (74) "Lovely quiet retreat. Comfortable, spacious, and nicely decorated " CA $105 CA $290 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Cumberland-Hotels-The-Board-Room-Enchanted-Table-Meadow-Near-Deep-Creek-Lake-Wisp-Forest-View.h49184146.Hotel-Information) ![Smart TV, DVD player, books](https://images.trvl-media.com/lodging/75000000/74300000/74291600/74291516/871cba83.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/75000000/74300000/74291600/74291516/9a285996.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/75000000/74300000/74291600/74291516/600e4429.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/75000000/74300000/74291600/74291516/2c1bd3d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern, spacious Loft with Riverside Deck just off GAP trail Confluence 10/10 Exceptional (47) "We stopped off at Casselman River Loft on our drive to Kentucky for Thanksgiving. We felt right at home when we arrived. The loft is very nicely appointed and equipped with all the essentials. We hope to return! " CA $281 CA $617 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Confluence-Hotels-Brand-New-Spacious-Loft-With-River-View-Just-Off-GAP-Trail.h74291516.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/71000000/70510000/70501900/70501827/4701ffab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/71000000/70510000/70501900/70501827/8f0e1025.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/71000000/70510000/70501900/70501827/375f861b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/71000000/70510000/70501900/70501827/67d30d03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stunning modern farmhouse with Lake Access and Free Golf! Swanton 10/10 Exceptional (18) "It was a wonderful experience and host was so friendly and gracious!" CA $1,453 CA $2,398 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Swanton-Hotels-6-Bedroom.h70501827.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/49000000/48610000/48604500/48604478/87ad376f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![10 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/49000000/48610000/48604500/48604478/edca1a44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/49000000/48610000/48604500/48604478/4cd29209.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, stereo](https://images.trvl-media.com/lodging/49000000/48610000/48604500/48604478/2f769502.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Farm, Near Lake, 10 Acres, Newly Renovated Swanton 9.8/10 Exceptional (10) "Fantastic place to have a group gathering for married couples. We all had an amazing time! The place was beautiful. The host was gracious. Looking forward to returning again. " CA $2,106 CA $3,014 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Swanton-Hotels-Historic-Farm.h48604478.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/22000000/21620000/21616600/21616516/1aa883f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/22000000/21620000/21616600/21616516/71414455.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/22000000/21620000/21616600/21616516/6947c5b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/22000000/21620000/21616600/21616516/1d222bd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cedar Lodge | 4BR, 2BA, Hot Tub, Fireplace, Private Yard Farmington 8.8/10 Excellent (180) "Great property! Clean, well stocked, and the hot tub was fabulous!" CA $474 CA $894 total includes taxes & fees Oct 17 - Oct 18 [](https://www.expedia.ca/Farmington-Hotels-Cedar-Lodge-4BR.h21616516.Hotel-Information) ![TV, fireplace, foosball, table tennis](https://images.trvl-media.com/lodging/22000000/21620000/21616500/21616421/a1c5e32a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/22000000/21620000/21616500/21616421/aab7f836.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/22000000/21620000/21616500/21616421/40140f25.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/22000000/21620000/21616500/21616421/ee019cc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chief Nemacolin's Lodge | 3BR, 3BA, Hot Tub, Fireplace, Private & Spacious, Sleeps 14! Farmington 9.2/10 Wonderful (130) "The lodge was a perfect weekend getaway. Beautiful scenery tucked away in the green woods of PA. Our group had a fantastic time, and enjoyed the river the lodge resides on. " CA $632 CA $1,180 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Farmington-Hotels-OVRs-Chief-Nemacolins-Lodge-Sleeps-14.h21616421.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=2025-10-30&endDate=2025-10-31®ionId=9160&adults=2&specialized_stays_group_explore=historic_property&sort=RECOMMENDED&openPlayBack=true) ## Top Oakland Hotel Reviews ## Frequently asked questions ### What should a history buff expect from a stay in Oakland? > Sights with historical relevance in Oakland are probably at the top of your sightseeing list. Why not appreciate the lakeside during your visit? ### How many historical hotels will I find in Oakland? > Oakland is home to 901 hotel accommodations bookable on Expedia though you won't find many designated historic hotels. ### What are the top historical sites and other places to visit in Oakland? > Favorite places to visit include Deep Creek Lake, Herrington Manor State Park, and Swallow Falls State Park. A couple of additional sights to add to your agenda are Youghiogheny River and Broadford Park. ### What is a historic hotel like in Oakland? > By booking a historic hotel, guests can stay in a place that has an official historic designation. A castle, stately home, palace or even a pub, lodge, old police station, or skyscraper can be identified as a historic hotel as long as it's a place of special interest. Traditional architecture and period features are often preserved in the guestrooms or communal spaces of such hotels in Oakland, giving a real sense of character. ### What is the difference between a historic hotel and a heritage hotel? > "Heritage hotel" is more common in Asia and Europe, while "historic hotel" is more common in the U.S. overall though the terms are similar. The architecture and actual building of historic hotels are generally the most important aspect. For a heritage hotel, mainly, it's cultural value along with how it inspired the community. ### Do historic hotels in Oakland have modern facilities? > Hotel interiors feature the modern conveniences and safety features you've come to expect, but every effort is made to preserve treasured traditions and historic facades. Private rooms with updated bathroom facilities, heating and air conditioning, free and fast Internet, and the normal amenities found at a contemporary hotel will be available in a historic hotel. 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[Chalets in Swanton](https://www.expedia.ca/Swanton-Chalets.d164144-aaChalets.Travel-Guide-Accommodation) - [Honeymoon Resorts and in Swanton](https://www.expedia.ca/Swanton-Hotels-Honeymoon-Hotels.0-0-d164144-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Swanton Hotels](https://www.expedia.ca/Swanton-Hotels.d164144.Travel-Guide-Hotels) - [Motels in Swanton](https://www.expedia.ca/Swanton-Motels.d164144-aaMotels.Travel-Guide-Accommodation) - [Thayerville Hotels](https://www.expedia.ca/Thayerville-Hotels.d553248635975871934.Travel-Guide-Hotels) - [Vacation Homes in Thayerville](https://www.expedia.ca/Thayerville-Private-Vacation-Homes.d553248635975871934-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Honeymoon Resorts and in The View](https://www.expedia.ca/The-View-Oakland-Hotels-Honeymoon-Hotels.0-n553248635976471573-0-tHoneymoonHotels.Travel-Guide-Filter-Hotels) - [Hotels with Balconies in The View](https://www.expedia.ca/The-View-Oakland-Hotels-Hotels-With-Balconies.0-n553248635976471573-0-tHotelswithBalconies.Travel-Guide-Filter-Hotels) - [Hotels with an Indoor Pool in The View](https://www.expedia.ca/The-View-Oakland-Hotels-Hotels-With-Indoor-Pool.0-n553248635976471573-0-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels) - [Hotels with smoking rooms in The View](https://www.expedia.ca/The-View-Oakland-Hotels-Hotels-With-Smoking-Rooms.0-n553248635976471573-0-tHotelswithsmokingrooms.Travel-Guide-Filter-Hotels) - [Mountain Hotels in The View](https://www.expedia.ca/The-View-Oakland-Hotels-Mountain-Hotels.0-n553248635976471573-0-tMountainHotels.Travel-Guide-Filter-Hotels) - [Hotel Wedding Venues Hotels in The View](https://www.expedia.ca/The-View-Oakland-Hotels-Wedding-Hotels.0-n553248635976471573-0-tWeddingHotels.Travel-Guide-Filter-Hotels) - [Winery Hotels in The View](https://www.expedia.ca/The-View-Oakland-Hotels-Winery-Hotel.0-n553248635976471573-0-tWineryHotel.Travel-Guide-Filter-Hotels) - [Winery Hotels in Waterfront Greens](https://www.expedia.ca/Waterfront-Greens-Swanton-Hotels-Winery-Hotel.0-n553248635976482173-0-tWineryHotel.Travel-Guide-Filter-Hotels) - [Waterfront Greens Hotels](https://www.expedia.ca/Waterfront-Greens-Swanton-Hotels.0-n553248635976482173-0.Travel-Guide-Filter-Hotels) - [Hotels near Wisp Resort](https://www.expedia.ca/Wisp-Resort-Hotels.0-l6091719-0.Travel-Guide-Filter-Hotels) - [Flights to McHenry](https://www.expedia.ca/Cheap-Flights-To-McHenry.d131592.Travel-Guide-Flights) - [Flights from Luke](https://www.expedia.ca/lp/flights/55806/flights-from-luke) - [Flights from Boston (BOS) to Oakland (ODM)](https://www.expedia.ca/lp/flights/bos/odm/boston-to-oakland) - [Flights from Cleveland (CLE) to Oakland (ODM)](https://www.expedia.ca/lp/flights/cle/odm/cleveland-to-oakland) - [Flights from New York (JFK) to Oakland (ODM)](https://www.expedia.ca/lp/flights/jfk/odm/new-york-to-oakland) - [Deep Creek Lake](https://www.expedia.ca/Deep-Creek-Lake-Maryland.d553248635959734861.Vacation-Attraction) - [Friendsville Vacations](https://www.expedia.ca/Friendsville.d6338432.Destination-Travel-Guides) - [Funland](https://www.expedia.ca/Funland-McHenry.d553248621532660290.Vacation-Attraction) - [Visit Thayerville](https://www.expedia.ca/Thayerville.dx553248635975871934) - [Wisp Resort](https://www.expedia.ca/Wisp-Resort-McHenry.d6091719.Vacation-Attraction) - [Car rental McHenry](https://www.expedia.ca/Car-Rentals-In-McHenry.d131592.Car-Rental-Guide) - [Book Historic Hotels in Oakland on Expedia.com](https://www.expedia.com/Oakland-Hotels-Historic-Hotel.0-0-d9160-tHistoricHotel.Travel-Guide-Filter-Hotels)