A river flowing through a forest with a waterfall.

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Our top choices for Oakland 4-star hotels

House (2 Bedrooms) | Property amenity

Loft of Luxury by Taylor Made Deep Creek

Loft of Luxury by Taylor Made Deep Creek
4.0 star property
Oakland
8.0 out of 10, Very Good, (2 reviews)
"Pasamos un buen tiempo en familia lo recomiendo es un buen lugar para visitar "
Mexico
Cesar
Loft of Luxury by Taylor Made Deep Creek
House (5 Bedrooms) | Property amenity

Bear Hollow Lodge by Taylor Made Deep Creek

Bear Hollow Lodge by Taylor Made Deep Creek
4.0 star property
Oakland
Bear Hollow Lodge by Taylor Made Deep Creek
House (3 Bedrooms) | Property amenity

Strawberry Fields by Taylor Made Deep Creek

Strawberry Fields by Taylor Made Deep Creek
4.0 star property
Oakland
10.0 out of 10, Exceptional, (1 review)
Strawberry Fields by Taylor Made Deep Creek
House (3 Bedrooms) | Property amenity

The Mountain Airy by Taylor Made Deep Creek

The Mountain Airy by Taylor Made Deep Creek
4.0 star property
Oakland
10.0 out of 10, Exceptional, (1 review)
"The whole house was beautiful and clean we loved our stay the hot tub was lovely and the chimney made it very cozy "
United States
Yesenia
The Mountain Airy by Taylor Made Deep Creek
House (4 Bedrooms) | Property amenity

Bears Lair by Taylor Made Deep Creek

Bears Lair by Taylor Made Deep Creek
4.0 star property
Oakland
10.0 out of 10, Exceptional, (1 review)
"The property was more than expected and we had a wonderful time. Everything we wanted to do was within driving distance. Wonderful experience!"
United States
Diane
Bears Lair by Taylor Made Deep Creek
House (3 Bedrooms) | Property amenity

Windy Acres by Taylor Made Deep Creek

Windy Acres by Taylor Made Deep Creek
4.0 star property
Oakland
4.0 out of 10, (1 review)
"The location was beautiful and loved we were able to bring our dogs but the stay itself was so uncomfortable we left a day early. The beds were extremely uncomfortable and while the house sleeps 11 people there was only 4 stools around a narrow island to sit and eat. The hot tub was unsanitary/poorly maintained with a thick scum ring along with waterline and filter area. The master bathroom window offered no privacy since there was no blinds or curtains. The listing also did not mention anything...
United States
Shannon
Windy Acres by Taylor Made Deep Creek
House (4 Bedrooms) | Property amenity

Mountain Freedom by Taylor Made Deep Creek

Mountain Freedom by Taylor Made Deep Creek
4.0 star property
Mountainside
Mountain Freedom by Taylor Made Deep Creek
House (3 Bedrooms) | Property amenity

Sidetracked by Taylor Made Deep Creek

Sidetracked by Taylor Made Deep Creek
4.0 star property
Mountainside
Sidetracked by Taylor Made Deep Creek
House (4 Bedrooms) | Property amenity

Butterfly Retreat by Taylor Made Deep Creek

Butterfly Retreat by Taylor Made Deep Creek
4.0 star property
Mountainside
Butterfly Retreat by Taylor Made Deep Creek
House (5 Bedrooms) | Property amenity

Lakestar Chalet by Taylor Made Deep Creek

Lakestar Chalet by Taylor Made Deep Creek
4.0 star property
Oakland
8.0 out of 10, Very Good, (1 review)
"Property matched description. It could’ve been a bit cleaner on arrival. The tvs did not work, but everything else was great. "
United States
Pamela
Lakestar Chalet by Taylor Made Deep Creek
House (4 Bedrooms) | Property amenity

Home Sweet Cabin by Taylor Made Deep Creek

Home Sweet Cabin by Taylor Made Deep Creek
4.0 star property
Oakland
Home Sweet Cabin by Taylor Made Deep Creek
House (2 Bedrooms) | Property amenity

A Beautiful View by Taylor Made Deep Creek

A Beautiful View by Taylor Made Deep Creek
4.0 star property
Oakland
6.8 out of 10, (3 reviews)
"Cute place with updated furnishings and appliances, right across the street from Deep Creek Lake boat rentals, jet skis, restaurants and Lakeside Creamery. 15 minute drive to Swallow Falls and quick drive to any other activity offered."
United States
Jamie
A Beautiful View by Taylor Made Deep Creek
House (4 Bedrooms) | Property amenity

Acorn Cottage by Taylor Made Deep Creek

Acorn Cottage by Taylor Made Deep Creek
4.5 star property
Oakland
Acorn Cottage by Taylor Made Deep Creek
House (4 Bedrooms) | Property amenity

Wooded Bliss by Taylor Made Deep Creek

Wooded Bliss by Taylor Made Deep Creek
4.0 star property
Oakland
Wooded Bliss by Taylor Made Deep Creek
House (4 Bedrooms) | Property amenity

Some Kind of Wonderful by Taylor Made Deep Creek

Some Kind of Wonderful by Taylor Made Deep Creek
4.0 star property
Silver Ridge
Some Kind of Wonderful by Taylor Made Deep Creek
House (5 Bedrooms) | Property amenity

American Pride by Taylor Made Deep Creek

American Pride by Taylor Made Deep Creek
4.0 star property
Blakeslee
6.0 out of 10, (1 review)
"This is a spacious home with plenty of space for a large family gathering and most importantly graciously allows dogs. Very close to the WISP resort, and minutes away from the lake. Owners have thoughtfully included plenty of "extras" to make guests feel at home like board games, DVDs, a game room, and a well-appointed kitchen! Home however is starting to show lots of wear and tear. To mention a few; a non-working gas fireplace (a pretty big deal for winter stays) missing door handles on the...
United States
veronica
American Pride by Taylor Made Deep Creek
House (4 Bedrooms) | Property amenity

Windsor House by Taylor Made Deep Creek

Windsor House by Taylor Made Deep Creek
4.0 star property
Paradise Point
Windsor House by Taylor Made Deep Creek
House (Multiple Bedrooms) | Property amenity

St. Bart's Retreat by Taylor Made Deep Creek

St. Bart's Retreat by Taylor Made Deep Creek
4.0 star property
Oakland
St. Bart's Retreat by Taylor Made Deep Creek
House (4 Bedrooms) | Property amenity

Bee Tree II by Taylor Made Deep Creek

Bee Tree II by Taylor Made Deep Creek
4.0 star property
Oakland
Bee Tree II by Taylor Made Deep Creek
House (4 Bedrooms) | Property amenity

A Winter View by Taylor Made Deep Creek

A Winter View by Taylor Made Deep Creek
4.0 star property
Oakland
6.0 out of 10, (2 reviews)
"Great place for a weekend getaway!"
United States
Andrea
A Winter View by Taylor Made Deep Creek
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Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Oakland.
Preston on the Lake 5 Bedroom House

Preston on the Lake 5 Bedroom House

585 Glendale Road Oakland MD
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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.

Learn more about Oakland

Nestled beside Deep Creek Lake, this mountain town offers year-round adventures from skiing to kayaking. Explore the historic downtown where local shops and farm-to-table restaurants welcome you in hiking boots after a day outdoors.

See all hotels in Oakland
A waterfall cascading over a rocky cliff into a river surrounded by trees.
Photo by Jenn Charbonneau
Open Photo by Jenn Charbonneau

Top Oakland Hotel Reviews

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Oakland?
To book a 4-star hotel in Oakland that fits your budget, use Expedia's handy filters. Check out the availability during your vacation dates and use our pricing filter to set your limit. You can also sort your results by the most affordable escape first.

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What's the difference between 5-star and 4-star hotels in Oakland?
Offering a welcoming guest experience and upscale surroundings, 4-star hotels are a fantastic option for your Oakland break. These types of stays generally feature lots of handy amenities that make it a breeze to unpack and relax — think large beds, bathrobes, gyms and pools. Or get a taste of the high life at a 5-star hotel designed to indulge you in exclusive perks and amenities. Round-the-clock concierge service, premium toiletries and fine dining are typically included at these plush properties.
Does Oakland have any 4-star all-inclusive resorts?
Enjoy a relaxing vacation experience where everything is included in the one upfront price by using our "All inclusive" filter. Budgeting is a breeze when your room, food, activities and entertainment are already taken care of. After more options? Browse the great deals on our standard 4-star stays in and around Oakland too.

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