A river flowing through a forest with a waterfall.

Find Romantic Hotels in Oakland, MD

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Oakland Romantic Hotels

Tonight
Sep 25 - Sep 26
Tomorrow
Sep 26 - Sep 27
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

Our top choices for Oakland romantic hotels

An indoor swimming pool with multiple lanes, a lifeguard chair, and a clock on the wall.
An aerial view of a property with a large grassy field, a house with a sloped roof, and dense forest surrounding it.
A gym with treadmills, weight machines, and exercise balls.
A bedroom with a wooden headboard, a bed with a quilted bedspread, a bedside table, and a window with curtains.

1. The Board Room-Enchanted Table Meadow. Near Deep Creek Lake & Wisp! Forest View!

The Board Room-Enchanted Table Meadow. Near Deep Creek Lake & Wisp! Forest View!
Accident
United States
Rachelle O.
￥13,573
￥37,609 total
includes taxes & fees
Sep 29 - Sep 30
The Board Room-Enchanted Table Meadow. Near Deep Creek Lake & Wisp! Forest View!
A cozy living room with a fireplace, a television, and a chandelier.
A kitchen with wooden cabinets, a microwave, an oven, and a coffee maker. There is a dining area with a table, chairs, and a chandelier.
A residential property with a wooden deck, a staircase leading to a second floor, and a front yard with a garden and a mailbox.
An indoor swimming pool with multiple lanes, a lifeguard chair, and a clock on the wall.

2. Butterfly Suite-Enchanted Elegance near DCL/Wisp! Fireplace! Meadow/Forest View!

Butterfly Suite-Enchanted Elegance near DCL/Wisp! Fireplace! Meadow/Forest View!
Accident
United States
Anne R.
￥13,573
￥32,580 total
includes taxes & fees
Sep 29 - Sep 30
Butterfly Suite-Enchanted Elegance near DCL/Wisp! Fireplace! Meadow/Forest View!
A cozy cabin interior with a leather couch, a chair, a dining table, and multiple windows offering views of the outdoors.
A rustic wooden cabin with a porch, surrounded by trees and a gravel path.
A spacious living room with a wooden dining table, comfortable seating, large windows, and a television.
A spacious living area with a wooden staircase, a dining table with chairs, a leather sofa, and a television mounted on the wall.

3. Minutes from Deep Creek Lake, Located on 24-acre farm with private 1-acre lake

Minutes from Deep Creek Lake, Located on 24-acre farm with private 1-acre lake
Accident
United States
Sid D.
￥37,148
￥81,655 total
includes taxes & fees
Sep 29 - Sep 30
Minutes from Deep Creek Lake, Located on 24-acre farm with private 1-acre lake
A cabin with a stone exterior, surrounded by dense forest.
A cozy living room with a fireplace, a dining area with chairs, a chandelier, and a view of the outdoors through a window.
A stone cabin with a wooden balcony, surrounded by trees.
A wooden door leading to a stone-paved entrance with a hanging light fixture.

4. Luxurious, rustic, private vacation home with great view.

Luxurious, rustic, private vacation home with great view.
Timberline
United States
Martin R.
￥42,021
￥90,247 total
includes taxes & fees
Oct 5 - Oct 6
Luxurious, rustic, private vacation home with great view.
A deck with two sofas and a table, overlooking a river and forested hills.
A modern kitchen with a large island, a dining area with a table and chairs, and a living area with a sofa and TV.
A modern kitchen with a brick accent wall, stainless steel appliances, and pendant lighting.
A living room with a sofa, a dining table with chairs, and large windows with a view of trees and hills.

5. Riverside Loft with Huge Deck on GAP Trail

Riverside Loft with Huge Deck on GAP Trail
Confluence
United States
Meghan R.
￥42,733
￥83,348 total
includes taxes & fees
Oct 5 - Oct 6
Riverside Loft with Huge Deck on GAP Trail
View all properties

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. If you'd like to explore around the area, you may want a rental car for your journey.

Explore a world of travel with Expedia