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Find 4 Star Hotels in Oakland, MD

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

Bear Hollow Lodge
Exterior

Bear Hollow Lodge

4.0 star property
Bear Hollow Lodge
A Beautiful View
Exterior

A Beautiful View

4.0 star property
8.0 out of 10, Very Good, (2)
"Beautiful view! I just wish the property management side of things was handled better. There really is no place to park, so it would probably be helpful if either a spot on the road was marked off for it, or at the least, if guests were allowed to park in the Taylor-Made Vacation Rental Office Building that is only 3 houses up the street. Also there is nowhere to put the trash for it to be picked up in front of the property. We were instructed to put the trash in the shed out back and it was...
A Beautiful View
Strawberry Fields
Exterior

Strawberry Fields

4.0 star property
10.0 out of 10, Exceptional, (1)
Strawberry Fields
Loft of Luxury
Outdoor spa tub

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
Paradise at Penn Cove
Exterior

Paradise at Penn Cove

4.0 star property
Paradise at Penn Cove
The Mountain Airy
Exterior

The Mountain Airy

4.0 star property
The Mountain Airy
Lazy Bear Cove
Exterior

Lazy Bear Cove

4.0 star property
Lazy Bear Cove
Mountain House
Exterior

Mountain House

4.0 star property
Mountain House
Some Kind of Wonderful
Exterior

Some Kind of Wonderful

4.0 star property
Some Kind of Wonderful
Deja Blue
Exterior

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
Waves N' Moguls
Exterior

Waves N' Moguls

4.0 star property
Waves N' Moguls
St. Bart's Retreat
Exterior

St. Bart's Retreat

4.0 star property
St. Bart's Retreat
Butterfly Retreat
Exterior

Butterfly Retreat

4.0 star property
Butterfly Retreat
Windsor House
Exterior

Windsor House

4.0 star property
Windsor House
Bears Lair
Exterior

Bears Lair

4.0 star property
Bears Lair
American Pride
Property grounds

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
Bee Tree II
Exterior

Bee Tree II

4.0 star property
Bee Tree II
A Winter View
Living area

A Winter View

4.0 star property
6.0 out of 10, (2)
"Great place for a weekend getaway!"
A Winter View
Old Moose Barn
Exterior

Old Moose Barn

4.0 star property
Old Moose Barn
Home Sweet Cabin
Exterior

Home Sweet Cabin

4.0 star property
Home Sweet Cabin
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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.

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 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.