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 26 - Sep 27
Tomorrow
Sep 27 - Sep 28
Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11

Our top choices for Oakland romantic hotels

A porch with hanging flower baskets and potted plants.
A sign for The Garrett Inn with a swan logo, surrounded by autumn foliage and decorative pumpkins.
A reception area with a wooden counter, a wall of informational brochures, a hanging lantern, and a framed map.
A motel with a red roof, a porch with potted plants, and a small outdoor seating area.

1. The Garrett Inn

The Garrett Inn
Oakland
United States
Tessa
￥23,549
￥27,247 total
includes taxes & fees
Oct 18 - Oct 19
The Garrett Inn
A cabin with a deck and a fire pit in the foreground.
A compact kitchen with white cabinets, a black refrigerator, and a microwave on top. There is a wooden table with two stools and a patterned rug on the floor.
A cozy interior of a yurt with a living area, kitchenette, and a ceiling fan.
A yurt with a wooden staircase leading to a red door, surrounded by trees and a wooden deck.

2. Deer Pass – Luxury Glamping Yurt Near Deep CreekMd

Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
Oakland
United States
Holly M.
￥18,874
￥38,298 total
includes taxes & fees
Oct 27 - Oct 28
Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
A spacious living area with a stone fireplace, wooden beams, a staircase, and a view of a lake.
A living room with a sofa, two armchairs, a coffee table, and a fireplace.
A lakeside view with boats docked, a sandy beach, and a forested hill in the background.
An outdoor seating area with tables and umbrellas, a wooden deck, and potted plants.

3. Suites at Silver Tree: A212 One Bedroom Standard View

Suites at Silver Tree: A212 One Bedroom Standard View
Oakland
United States
Erin C.
￥33,406
￥41,416 total
includes taxes & fees
Sep 30 - Oct 1
Suites at Silver Tree: A212 One Bedroom Standard View
A spacious lobby with a stone fireplace, wooden beams, and a high ceiling.
A multi-story lodge with a stone facade, wooden balconies, and a snow-covered ground.
An outdoor seating area with tables and umbrellas, a wooden deck, and potted plants.
A hotel room with a bed, a sofa, a desk, a television, and a kitchenette.

4. Suites at Silver Tree: A210 Studio Standard View

Suites at Silver Tree: A210 Studio Standard View
Oakland
United States
Darlene
￥31,785
￥39,570 total
includes taxes & fees
Sep 30 - Oct 1
Suites at Silver Tree: A210 Studio Standard View
A spacious living area with a stone fireplace, wooden beams, a staircase, and a view of a lake.
A hotel room with a bed, a sofa, a dining table, and a TV.
A lakeside view with boats docked, a sandy beach, and a forested hill in the background.
An outdoor seating area with tables and umbrellas, a wooden deck, and potted plants.

5. Suites at Silver Tree: A124 Studio Standard View

Suites at Silver Tree: A124 Studio Standard View
Oakland
United States
Lisa G.
￥32,082
￥41,118 total
includes taxes & fees
Sep 29 - Sep 30
Suites at Silver Tree: A124 Studio Standard View
A spacious lobby with a stone fireplace, wooden beams, and a high ceiling.
A hotel room with a kitchenette, a bed, a bedside table, and a welcome book.
An outdoor seating area with tables and umbrellas, a wooden deck, and potted plants.
A multi-story lodge with a stone facade, wooden balconies, and a snow-covered ground.

6. Suites at Silver Tree: A118 Studio Standard View

Suites at Silver Tree: A118 Studio Standard View
Oakland
United States
Mark
￥31,605
￥39,365 total
includes taxes & fees
Oct 7 - Oct 8
Suites at Silver Tree: A118 Studio Standard View
A dining area with a wooden table and chairs, a brick accent wall, and pendant lighting.
A modern living room with a large TV, white furniture, and a view of the outdoors.

7. Will O' The Wisp: 107B One Bedroom/One Bath

Will O' The Wisp: 107B One Bedroom/One Bath
Mountainside
United States
Stacy S.
￥38,718
￥49,523 total
includes taxes & fees
Sep 29 - Sep 30
Will O' The Wisp: 107B One Bedroom/One Bath
A bedroom with a large bed, a ceiling fan, a nightstand with a lamp, and a view of a lake through the window.
A cozy restaurant with a stone fireplace, wooden furniture, and large windows allowing natural light.

8. Will O' The Wisp: 708H Studio Loft/One Bath

Will O' The Wisp: 708H Studio Loft/One Bath
Oakland
United States
Tyler M.
￥35,350
￥43,634 total
includes taxes & fees
Oct 7 - Oct 8
Will O' The Wisp: 708H Studio Loft/One Bath
A spacious living area with a stone fireplace, wooden beams, a staircase, and a view of a lake.
A large resort with multiple buildings, outdoor seating areas, and a parking lot.
A multi-story hotel with outdoor seating areas, balconies, and a wooden deck.
A wooden deck with a view of a lake and dock area.

9. Suites at Silver Tree: A115 One Bedroom Lake View

Suites at Silver Tree: A115 One Bedroom Lake View
Oakland
United States
Angela
￥35,657
￥43,983 total
includes taxes & fees
Sep 28 - Sep 29
Suites at Silver Tree: A115 One Bedroom Lake View
A spacious lobby with a stone fireplace, wooden beams, and a high ceiling.
A multi-story lodge with a stone facade, wooden balconies, and a snow-covered ground.
A lakeside view with boats docked, a sandy beach, and a forested hill in the background.
A spacious kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, and a sink. There is a dining area with a table and chairs, and a living room with a sofa and a window.

10. Suites at Silver Tree: A218 One Bedroom Standard View

Suites at Silver Tree: A218 One Bedroom Standard View
Oakland
United States
Ann Mahling
￥33,406
￥41,416 total
includes taxes & fees
Oct 1 - Oct 2
Suites at Silver Tree: A218 One Bedroom Standard View
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