Title: Book the Best ROMANTIC Hotels in Oakland, MD from CA $287 - Oakland Romantic Getaways | 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 Romantic Hotels in Oakland, MD from CA $287 ### Change your mind Book hotels with free cancellation ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ### Be picky Search almost a million properties worldwide ## Check availability on Oakland Romantic Hotels Tonight [Oct 7 - Oct 8](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-10-07&endDate=2025-10-08&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 8 - Oct 9](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-10-08&endDate=2025-10-09&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-10-10&endDate=2025-10-12&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-10-17&endDate=2025-10-19&adults=2&travelerType=ROMANTIC&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Oakland Romantic Hotels ![Exterior](https://images.trvl-media.com/lodging/33000000/32820000/32818400/32818307/b818e0b6.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) ![Pool](https://images.trvl-media.com/lodging/33000000/32820000/32818400/32818307/b0aebc14.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) ### 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 $287 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/d313359f.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) ![Property grounds](https://images.trvl-media.com/lodging/50000000/49190000/49184200/49184146/b5edd8d3.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 $287 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) ![Superior Cabin, 1 King Bed, Hot Tub, Lake View | Private kitchen](https://images.trvl-media.com/lodging/7000000/6660000/6655000/6654948/ef76c434.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![C 51R - Comfort Cabin, 2 Queen Beds, Pet Friendly, Mountainside (May hear neighbors) | Living area](https://images.trvl-media.com/lodging/7000000/6660000/6655000/6654948/6b3a0b2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/7000000/6660000/6655000/6654948/1b2becf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![C 4-Luxury Cabin, 1 King Bed, Kitchen, Lakeside](https://images.trvl-media.com/lodging/7000000/6660000/6655000/6654948/af73a6fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Lodges at Sunset Village McHenry 9.2/10 Wonderful (358) "Great place and we brought our dog. The cabins were quiet, clean, and we had everything we needed. Front desk was very responsive. " CA $277 CA $316 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Cumberland-Hotels-The-Lodges-At-Sunset-Village.h6654948.Hotel-Information) ![The Grand Lodge Accessible Patio Suite | Terrace/patio](https://images.trvl-media.com/lodging/1000000/860000/857000/856941/42e14bb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/860000/857000/856941/1c9113a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/860000/857000/856941/8ba183dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cafe](https://images.trvl-media.com/lodging/1000000/860000/857000/856941/40b4d4b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Nemacolin Farmington 9.2/10 Wonderful (458) "Our stay was relaxing." CA $1,246 CA $1,456 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Uniontown-Hotels-Nemacolin.h856941.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) ![Interior](https://images.trvl-media.com/lodging/49000000/48610000/48604500/48604478/04faed71.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 $2,092 CA $2,913 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Swanton-Hotels-Historic-Farm.h48604478.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) ![Property grounds](https://images.trvl-media.com/lodging/75000000/74300000/74291600/74291516/2c1bd3d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74300000/74291600/74291516/ca549835.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) ### Modern, spacious Loft with River View just off GAP trail Confluence 10/10 Exceptional (47) "Lovely, tastefully decorated home with an amazing river view and a fully equipped kitchen where we made several meals. Direct access to GAP trail, for biking to Ohiopyle and Pinkerton bridges. Beautiful hikes nearby with waterfall Bald Eagle sighting and spring wild flowers. People with mobility problems may struggle with stairs. " CA $279 CA $613 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) ![Outdoor spa tub](https://images.trvl-media.com/lodging/22000000/21630000/21625600/21625514/07608a23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/22000000/21630000/21625600/21625514/5fb126ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, DVD player](https://images.trvl-media.com/lodging/22000000/21630000/21625600/21625514/5a9f2bca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/22000000/21630000/21625600/21625514/1f0de926.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pura Vida | 3BR, 2BA, Hot Tub, Private, Dog Friendly, Borders State Park! Ohiopyle 9.2/10 Wonderful (192) "Nice quiet getaway. " CA $471 CA $882 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Ohiopyle-Hotels-Pura-Vida-3BR.h21625514.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33490000/33485700/33485657/97c76b62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33490000/33485700/33485657/4b525057.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/34000000/33490000/33485700/33485657/ee94c3e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books, video library](https://images.trvl-media.com/lodging/34000000/33490000/33485700/33485657/55bbf16b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Minutes from Deep Creek Lake, Located on 24-acre farm with private 1-acre lake Accident 10/10 Exceptional (214) "The house and property were exactly what we were looking for. Private, but close enough to everything. House had everything you need for your stay. Would recommend. " CA $272 CA $645 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Accident-Hotels-Minutes-From-Deep-Creek-Lake.h33485657.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) ![TV, fireplace, DVD player, stereo](https://images.trvl-media.com/lodging/22000000/21620000/21616600/21616516/e9d4fddd.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) ![Interior](https://images.trvl-media.com/lodging/22000000/21620000/21616600/21616516/71414455.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 (179) "Great property! Clean, well stocked, and the hot tub was fabulous!" CA $471 CA $882 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Farmington-Hotels-Cedar-Lodge-4BR.h21616516.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=2025-10-21&endDate=2025-10-22®ionId=9160&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## Top Oakland Hotel Reviews ## Frequently asked questions ### Searching for romantic hotels in Oakland? > Are you looking for a romantic getaway? Our guests also enjoy Oakland for its lakeside setting and riverfront. You might consider checking out some of the nearby sights and attractions such as Deep Creek Lake, Herrington Manor State Park, or Swallow Falls State Park. If you'd like to stay close to a certain attraction, you can sort properties by neighborhood or distance to top sights, so you'll be able to see everything on your list. ### When is the best time of year for a romantic getaway to Oakland? > If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Oakland: The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 32°F. The snowiest months in Oakland are January, December, February, and May, with each month seeing an average of 31 inches of snowfall. ### What is there to do in Oakland? > There's nothing better than wandering around a new destination with your sweetheart, so consider checking out all there is to see and do in Oakland. Couples looking to see some of the area's natural features will enjoy Oakland for its lakeside setting and riverfront. You might think about visiting Deep Creek Lake, Herrington Manor State Park, or Swallow Falls State Park. ### What's the best way to get to Oakland and around town during my romantic getaway? > These transportation options in Oakland might help your romantic trip get off to a smooth start: If you're looking to fly to Oakland, the closest major airport is Morgantown, WV (MGW-Morgantown Municipal), located 31.8 mi (51.2 km) from the city center. 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[Paradise Point Hotels](https://www.expedia.ca/Paradise-Point-Oakland-Hotels.0-n553248635976481309-0.Travel-Guide-Filter-Hotels) - [Silver Ridge Hotels](https://www.expedia.ca/Silver-Ridge-Oakland-Hotels.0-n553248635976471096-0.Travel-Guide-Filter-Hotels) - [Hotels with Hot Tubs in Sky Valley](https://www.expedia.ca/Sky-Valley-Swanton-Hotels-Hotels-With-Hot-Tubs.0-n553248635976480653-0-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels) - [Mountain Hotels in Sky Valley](https://www.expedia.ca/Sky-Valley-Swanton-Hotels-Mountain-Hotels.0-n553248635976480653-0-tMountainHotels.Travel-Guide-Filter-Hotels) - [Spa Hotels in Sky Valley](https://www.expedia.ca/Sky-Valley-Swanton-Hotels-Spa-Hotel.0-n553248635976480653-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Sky Valley Hotels](https://www.expedia.ca/Sky-Valley-Swanton-Hotels.0-n553248635976480653-0.Travel-Guide-Filter-Hotels) - [Hotels near Swallow Falls State Park](https://www.expedia.ca/Swallow-Falls-State-Park-Hotels.0-l553248621532660285-0.Travel-Guide-Filter-Hotels) - [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 Romantic Hotels in Oakland on Expedia.com](https://www.expedia.com/Oakland-Hotels-Romantic-Hotel.0-0-d9160-tRomanticHotel.Travel-Guide-Filter-Hotels)