Photo by KM Moore

Compare and book 4 Star hotels in Oakland, Maryland

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Check availability on Oakland 4 Star Hotels

Tonight
5 Jul - 6 Jul
Tomorrow
6 Jul - 7 Jul
Next weekend
11 Jul - 13 Jul
In two weeks
18 Jul - 20 Jul

Top Oakland 4 Star Hotels

Bear Hollow Lodge
House (5 Bedrooms) | Front of property

Bear Hollow Lodge

4.0 star property
Bear Hollow Lodge
Loft of Luxury
House (2 Bedrooms) | Property amenity

Loft of Luxury

4.0 star property
8.0 out of 10, Very good, (2)
"Pasamos un buen tiempo en familia lo recomiendo es un buen lugar para visitar "
Loft of Luxury
Strawberry Fields
House (3 Bedrooms) | Property amenity

Strawberry Fields

4.0 star property
10.0 out of 10, Exceptional, (1)
Strawberry Fields
Lakestar Chalet
House (5 Bedrooms) | Property amenity

Lakestar Chalet

4.0 star property
Lakestar Chalet
Mountain House
House (5 Bedrooms) | Property amenity

Mountain House

4.0 star property
Mountain House
Butterfly Retreat
House (4 Bedrooms) | Property amenity

Butterfly Retreat

4.0 star property
Butterfly Retreat
Waves N' Moguls
House, Multiple Beds, Hot Tub | View from property

Waves N' Moguls

4.0 star property
Waves N' Moguls
Bears Lair
House (4 Bedrooms) | Property amenity

Bears Lair

4.0 star property
10.0 out of 10, Exceptional, (1)
"The property was more than expected and we had a wonderful time. Everything we wanted to do was within driving distance. Wonderful experience!"
Bears Lair
Windsor House
House (4 Bedrooms) | Property amenity

Windsor House

4.0 star property
Windsor House
Paradise at Penn Cove
3 bedrooms, free WiFi, bed sheets

Paradise at Penn Cove

4.0 star property
Paradise at Penn Cove
Deja Blue
Aerial view

Deja Blue

4.0 star property
10.0 out of 10, Exceptional, (1)
"Deja Blue was extremely clean and comfortable for my family get away. Provided all neede items. I will definitely use Taylor Made again"
Deja Blue
A Beautiful View
House (2 Bedrooms) | Front of property

A Beautiful View

4.0 star property
8.0 out of 10, Very good, (2)
"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."
A Beautiful View
Lazy Bear Cove
House (4 Bedrooms) | Property amenity

Lazy Bear Cove

4.0 star property
Lazy Bear Cove
The Mountain Airy
House (3 Bedrooms) | Property amenity

The Mountain Airy

4.0 star property
The Mountain Airy
Bee Tree II
House (4 Bedrooms) | Front of property

Bee Tree II

4.0 star property
Bee Tree II
Mountain Freedom
House (4 Bedrooms) | Property amenity

Mountain Freedom

4.0 star property
Mountain Freedom
Some Kind of Wonderful
House (4 Bedrooms) | Property amenity

Some Kind of Wonderful

4.0 star property
Some Kind of Wonderful
American Pride
House (5 Bedrooms) | Property amenity

American Pride

4.0 star property
6.0 out of 10, (1)
"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...
American Pride
St. Bart's Retreat
House (Multiple Bedrooms) | Front of property

St. Bart's Retreat

4.0 star property
St. Bart's Retreat
A Winter View
House (4 Bedrooms) | Front of property

A Winter View

4.0 star property
6.0 out of 10, (2)
"Great place for a weekend getaway!"
A Winter View
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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 city centre where local shops and farm-to-table restaurants welcome you in hiking boots after a day outdoors.

See all hotels in Oakland
Photo by KM Moore
Open Photo by KM Moore

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 holiday dates and use our pricing filter to set your limit. You can also sort your results by the most affordable escape first.

  • Search for the lowest price

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 holiday 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.