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) ![Waterfall at Swallow Falls](https://images.trvl-media.com/place/9160/b8baa833-4ced-4ac5-b870-e726bd5ccf56.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Jenn Charbonneau ![](https://images.trvl-media.com/place/9160/b8baa833-4ced-4ac5-b870-e726bd5ccf56.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 [Jan 29 - Jan 30](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2026-01-29&endDate=2026-01-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [Jan 30 - Jan 31](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2026-01-30&endDate=2026-01-31&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) This weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Next weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=9160&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) ## Our top choices for Oakland romantic hotels ![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) ![Golf](https://images.trvl-media.com/lodging/50000000/49190000/49184200/49184146/0e825b72.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) ![2 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/50000000/49190000/49184200/49184146/2f460cf1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Board Room-Enchanted Table Meadow. Near Deep Creek Lake & Wisp! Forest View! [](https://www.expedia.ca/Cumberland-Hotels-The-Board-Room-Enchanted-Table-Meadow-Near-Deep-Creek-Lake-Wisp-Forest-View.h49184146.Hotel-Information) Accident 9.6/10 Exceptional (77 reviews) "The place was very nice and comfortable! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen J. CA $115 CA $314 total includes taxes & fees Feb 25 - Feb 26 [](https://www.expedia.ca/Cumberland-Hotels-The-Board-Room-Enchanted-Table-Meadow-Near-Deep-Creek-Lake-Wisp-Forest-View.h49184146.Hotel-Information) ![C 50R - Comfort Cabin, 1 King bed, Pet Friendly, Mountainside (May hear neighbors) | Living area](https://images.trvl-media.com/lodging/7000000/6660000/6655000/6654948/71f46570.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![C 49R - Comfort Cabin,1 King Bed, Pet Friendly, Mountainside (May hear neighbors) | Living area](https://images.trvl-media.com/lodging/7000000/6660000/6655000/6654948/81a17933.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![C 51L - Comfort Cabin, 2 Queen Beds, Pet Friendly, Mountainside (May hear neighbors)](https://images.trvl-media.com/lodging/7000000/6660000/6655000/6654948/bb88b8d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/7000000/6660000/6655000/6654948/49c1a433.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Lodges at Sunset Village [](https://www.expedia.ca/Cumberland-Hotels-The-Lodges-At-Sunset-Village.h6654948.Hotel-Information) McHenry 9.2/10 Wonderful (364 reviews) "Clean rooms and friendly staff. We would definitely stay here again while we ski at wisp resort." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jesse CA $252 CA $287 total includes taxes & fees Feb 15 - Feb 16 [](https://www.expedia.ca/Cumberland-Hotels-The-Lodges-At-Sunset-Village.h6654948.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/34000000/33490000/33485700/33485657/dba92839.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) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33490000/33485700/33485657/171fea67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books, video library](https://images.trvl-media.com/lodging/34000000/33490000/33485700/33485657/7ffcf41e.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 [](https://www.expedia.ca/Accident-Hotels-Minutes-From-Deep-Creek-Lake.h33485657.Hotel-Information) Accident 10/10 Exceptional (217 reviews) "Family friendly " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Henok CA $225 CA $575 total includes taxes & fees Feb 3 - Feb 4 [](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) ![Interior](https://images.trvl-media.com/lodging/75000000/74300000/74291600/74291516/3e155391.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books](https://images.trvl-media.com/lodging/75000000/74300000/74291600/74291516/0a8db4d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74300000/74291600/74291516/09a5deb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Riverside Loft with Huge Deck on GAP Trail [](https://www.expedia.ca/Confluence-Hotels-Brand-New-Spacious-Loft-With-River-View-Just-Off-GAP-Trail.h74291516.Hotel-Information) Confluence 10/10 Exceptional (48 reviews) "The Casselman River Loft was very well decorated, had a great view of the river and was centrally located to the town. The layout of the loft was very well suited for two couples or a family with children. The beds and sofas were extremely comfortable. We were visiting for a wedding and saw some of the other accommodations and ours was far superior. If visiting Confluence, I would highly recommend the Casselman River Loft." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shari V. CA $243 CA $560 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/Confluence-Hotels-Brand-New-Spacious-Loft-With-River-View-Just-Off-GAP-Trail.h74291516.Hotel-Information) ![Indoor pool, outdoor pool, open 6:30 AM to 8:00 PM, cabanas (surcharge)](https://images.trvl-media.com/lodging/1000000/860000/857000/856941/211f4749.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/860000/857000/856941/6a7ea2a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/1000000/860000/857000/856941/d95e1139.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Golf](https://images.trvl-media.com/lodging/1000000/860000/857000/856941/84d8ce8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Nemacolin [](https://www.expedia.ca/Uniontown-Hotels-Nemacolin.h856941.Hotel-Information) Nemacolin 9.2/10 Wonderful (467 reviews) "Room was immaculate " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Caitlin CA $1,011 CA $1,193 total includes taxes & fees Mar 2 - Mar 3 [](https://www.expedia.ca/Uniontown-Hotels-Nemacolin.h856941.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/49000000/48610000/48604500/48604478/2afc8213.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/49000000/48610000/48604500/48604478/e38393ea.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 [](https://www.expedia.ca/Swanton-Hotels-Historic-Farm.h48604478.Hotel-Information) Swanton 10/10 Exceptional (11 reviews) "The Historic Farm property was beautiful! Our family enjoyed fishing at the pond and biking in and around the property. We hiked and swam in the nearby State Parks. The bedrooms were spacious and the king sized beds comfortable. It was great to have meals with the whole family around the large dining room table. The ice machine in the cozy kitchen was an added bonus." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cheryl W. CA $2,226 CA $3,099 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Swanton-Hotels-Historic-Farm.h48604478.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/71000000/70130000/70129300/70129279/74eab84c.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/71000000/70130000/70129300/70129279/b0b0436e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/71000000/70130000/70129300/70129279/305a61f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/71000000/70130000/70129300/70129279/aa41cc1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### #1 Cabin\~Walk to WISP! Lake access & dock! HOT Tub\~Game room\~Fire Pit & DOGS OK! [](https://www.expedia.ca/McHenry-Hotels-Walk-To-Wisp-DEEP-CREEK-LAKEHOT-TUBGAME-ROOMFire-Pit-DOG-FRIENDLY.h70129279.Hotel-Information) McHenry 9.8/10 Exceptional (37 reviews) "Peaceful, relaxing, plenty of room" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) troy s. CA $363 CA $988 total includes taxes & fees Feb 2 - Feb 3 [](https://www.expedia.ca/McHenry-Hotels-Walk-To-Wisp-DEEP-CREEK-LAKEHOT-TUBGAME-ROOMFire-Pit-DOG-FRIENDLY.h70129279.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=2026-02-13&endDate=2026-02-14®ionId=9160&adults=2&travelerType=romantic&sort=RECOMMENDED&openPlayBack=true) ## Top Oakland Hotel Reviews ## Frequently asked questions ### Searching for romantic hotels in Oakland? ### When is the best time of year for a romantic getaway to Oakland? ### What is there to do in Oakland? ### What's the best way to get to Oakland and around town during my romantic getaway? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [2 Star Hotels in Paradise Point ](https://www.expedia.ca/2Star-Paradise-Point-Oakland-Hotels.s20-n553248635976481309-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Mountainside ](https://www.expedia.ca/5Star-Mountainside-Oakland-Hotels.s50-n553248635976481730-0.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Sunplace ](https://www.expedia.ca/5Star-Sunplace-McHenry-Hotels.s50-n553248635976468730-0.Travel-Guide-Filter-Hotels) - 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