Title: Book the Best ROMANTIC Hotels in Oakland, MD from CA $282 - 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 $282 ![](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 Romantic Hotels Tonight [Oct 22 - Oct 23](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-10-22&endDate=2025-10-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [Oct 23 - Oct 24](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-10-23&endDate=2025-10-24&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) This 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&travelerType=romantic) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) ## 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) ![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/e90d2cd6.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) ### 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 ! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amanda S. CA $113 CA $282 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) ![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) ![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 (75) "Lovely quiet retreat. Comfortable, spacious, and nicely decorated " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) S K. CA $105 CA $289 total includes taxes & fees Nov 5 - Nov 6 [](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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/7000000/6660000/6655000/6654948/1b2becf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Lodges at Sunset Village McHenry 9.2/10 Wonderful (359) "Great place and we brought our dog. The cabins were quiet, clean, and we had everything we needed. Front desk was very responsive. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kimberly CA $278 CA $317 total includes taxes & fees Nov 5 - Nov 6 [](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) ![Lobby](https://images.trvl-media.com/lodging/1000000/860000/857000/856941/208014c6.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." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Trudy CA $1,240 CA $1,450 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Uniontown-Hotels-Nemacolin.h856941.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) ![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) ![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) ### Minutes from Deep Creek Lake, Located on 24-acre farm with private 1-acre lake Accident 10/10 Exceptional (215) "Family friendly " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Henok CA $246 CA $613 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Accident-Hotels-Minutes-From-Deep-Creek-Lake.h33485657.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) ![Interior](https://images.trvl-media.com/lodging/75000000/74300000/74291600/74291516/600e4429.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) ### Modern, spacious Loft with Riverside Deck just off GAP trail Confluence 10/10 Exceptional (48) "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! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Timothy D. CA $280 CA $615 total includes taxes & fees Nov 5 - Nov 6 [](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) ![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) ![Exterior](https://images.trvl-media.com/lodging/22000000/21630000/21625600/21625514/5fb126ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/22000000/21630000/21625600/21625514/02fddfdd.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 (193) "Great place! Great property! Really enjoyed our stay! Thank you!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Beverly S. CA $472 CA $874 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Ohiopyle-Hotels-Pura-Vida-3BR.h21625514.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) ![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) ![Dining](https://images.trvl-media.com/lodging/49000000/48610000/48604500/48604478/4cd29209.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) ### 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. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Taifa G. CA $2,099 CA $2,921 total includes taxes & fees Nov 2 - Nov 3 [](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) ![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) ![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) ### 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!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rachel B. CA $472 CA $874 total includes taxes & fees Nov 2 - Nov 3 [](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=2025-11-06&endDate=2025-11-07®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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