Title: Book the Best ROMANTIC Hotels in Oakland, MD - 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 ![](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 18 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-10-18&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [Oct 19 - Oct 20](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2025-10-19&endDate=2025-10-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) 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&travelerType=romantic) In two weeks [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) ![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 ! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amanda S. CA $119 CA $288 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) ![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/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) ### 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 " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) S K. 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) ![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) ![Exterior](https://images.trvl-media.com/lodging/7000000/6660000/6655000/6654948/af85dd48.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 (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 $279 CA $318 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Cumberland-Hotels-The-Lodges-At-Sunset-Village.h6654948.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/75000000/74300000/74291600/74291516/600e4429.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) ![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) ### 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! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Timothy D. CA $280 CA $616 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) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33490000/33485700/33485657/97c76b62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33490000/33485700/33485657/5ac3b590.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 (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. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bradley P. CA $246 CA $614 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Accident-Hotels-Minutes-From-Deep-Creek-Lake.h33485657.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) ![Property amenity](https://images.trvl-media.com/lodging/1000000/860000/857000/856941/8ba183dc.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) ![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 $1,215 CA $1,422 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Uniontown-Hotels-Nemacolin.h856941.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) ![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) ![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) ### 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 $473 CA $891 total includes taxes & fees Oct 23 - Oct 24 [](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) ![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) ![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. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Taifa G. CA $2,103 CA $3,009 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) ![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 $473 CA $886 total includes taxes & fees Oct 20 - Oct 21 [](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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/22000000/21620000/21616500/21616421/bc0f5d7d.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. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey R. CA $631 CA $1,170 total includes taxes & fees Oct 20 - Oct 21 [](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=2025-11-02&endDate=2025-11-03®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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