Photo by Jenn Charbonneau

Find 4 Star Hotels in Oakland, MD

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Check availability on Oakland 4 Star Hotels

Tonight
23 Nov - 24 Nov
Tomorrow
24 Nov - 25 Nov
Next weekend
28 Nov - 30 Nov
In two weeks
5 Dec - 7 Dec

Compare Oakland 4 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

House (5 Bedrooms) | Property amenity
Bear Hollow Lodge

Bear Hollow Lodge

4.0 star property
Oakland
Bear Hollow Lodge
House (3 Bedrooms) | Property amenity
Strawberry Fields

Strawberry Fields

4.0 star property
Oakland
10.0 out of 10, Exceptional, (1)
Strawberry Fields
House (4 Bedrooms) | Property amenity
Bears Lair

Bears Lair

4.0 star property
Oakland
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!"
United States
Diane
Bears Lair
House (4 Bedrooms) | Property amenity
Acorn Cottage

Acorn Cottage

4.5 star property
Oakland
Acorn Cottage
House (2 Bedrooms) | Property amenity
Loft of Luxury

Loft of Luxury

4.0 star property
Oakland
8.0 out of 10, Very Good, (2)
"Pasamos un buen tiempo en familia lo recomiendo es un buen lugar para visitar "
Mexico
Cesar
Loft of Luxury
House (4 Bedrooms) | Property amenity
Butterfly Retreat

Butterfly Retreat

4.0 star property
Mountainside
Butterfly Retreat
House (4 Bedrooms) | Front of property
Bee Tree II

Bee Tree II

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

Mountain Freedom

4.0 star property
Mountainside
Mountain Freedom
House (4 Bedrooms) | Property amenity
Home Sweet Cabin

Home Sweet Cabin

4.0 star property
Oakland
Home Sweet Cabin
House (4 Bedrooms) | Property amenity
Windsor House

Windsor House

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

Lakestar Chalet

4.0 star property
Oakland
8.0 out of 10, Very Good, (1)
"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
House (2 Bedrooms) | Front of property
A Beautiful View

A Beautiful View

4.0 star property
Oakland
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."
United States
Jamie
A Beautiful View
House (5 Bedrooms) | Property amenity
Mountain House

Mountain House

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

Some Kind of Wonderful

4.0 star property
Silver Ridge
Some Kind of Wonderful
House (Multiple Bedrooms) | Property amenity
St. Bart's Retreat

St. Bart's Retreat

4.0 star property
Oakland
St. Bart's Retreat
House (3 Bedrooms) | Property amenity
The Mountain Airy

The Mountain Airy

4.0 star property
Oakland
The Mountain Airy
House (4 Bedrooms) | Property amenity
A Winter View

A Winter View

4.0 star property
Oakland
6.0 out of 10, (2)
"Great place for a weekend getaway!"
United States
Andrea
A Winter View
House, Multiple Beds, Hot Tub | View from property
Waves N' Moguls

Waves N' Moguls

4.0 star property
Oakland
Waves N' Moguls
3 bedrooms, free WiFi, bed sheets
Paradise at Penn Cove

Paradise at Penn Cove

4.0 star property
Oakland
Paradise at Penn Cove
House (5 Bedrooms) | Property amenity
American Pride

American Pride

4.0 star property
Blakeslee
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...
United States
veronica
American Pride
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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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PoolSpaHot tubBreakfast includedWaterpark
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
Waterfall at Swallow Falls
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.

  • 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 worry-free vacation experience where everything is included in the one upfront price by using our "All inclusive" filter. Sticking to your budget is a piece of cake when your room, meals and many activities are already taken care of. Eager for more options? Check out the great deals on our standard 4-star resorts in and around Oakland too.

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