Explore top 2026 4 Star Hotels in Oakland

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Top Oakland 4 Star hotels

Loft of Luxury by Taylor Made Deep Creek

Oakland MD

A restaurant and a hot tub are featured at this vacation home. Guests will appreciate free perks like free self parking and WiFi in public areas. Barbecue grills ...

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Bear Hollow Lodge by Taylor Made Deep Creek

20590 GARRETT HWY Oakland MD

This vacation home features a restaurant, free WiFi in public areas, and barbecue grills.

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Strawberry Fields by Taylor Made Deep Creek

10 ROMAN RIDGE RD #22A Oakland MD

A marina and a hot tub are featured at this smoke-free cabin. Enjoy a meal from the restaurant and perks like free self parking and free WiFi.

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The Mountain Airy by Taylor Made Deep Creek

130 WHITETAIL CT Oakland MD

A restaurant and a hot tub are featured at this cabin. WiFi in public areas is free. Barbecue grills are provided for your convenience.

10/10 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"

Reviewed on Nov 30, 2025

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Mountain Freedom by Taylor Made Deep Creek

705 MOUNTAINVIEW DR Oakland MD

A restaurant and free WiFi in public areas are featured at this vacation home.

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Bears Lair by Taylor Made Deep Creek

94 LEHMAN LN Oakland MD

This vacation home features an outdoor pool, a hot tub, and a restaurant. Guests will appreciate free perks like free self parking and WiFi in public areas.

10/10 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!"

Reviewed on Jun 18, 2025

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Windy Acres by Taylor Made Deep Creek

493 Herrington Manor Road Oakland MD

A restaurant is available at this vacation home.

4/10 (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 ..."

Reviewed on Jul 6, 2026

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Home Sweet Cabin by Taylor Made Deep Creek

350 MAPLE DEL LN Oakland MD

A restaurant and a hot tub are featured at this cabin. Guests will appreciate free perks like free self parking and WiFi in public areas. Barbecue grills are ...

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Sidetracked by Taylor Made Deep Creek

891 Mountainview Drive Oakland MD

A marina and a restaurant are featured at this smoke-free vacation home. WiFi in public areas is free.

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Butterfly Retreat by Taylor Made Deep Creek

1489 MOUNTAINVIEW DR Oakland MD

This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A restaurant and a terrace are also provided.

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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.

4 Star Hotels Oakland

Looking to live it up on your vacation with a bit of luxury? Or maybe you’ve decided that your boss can afford to put you up at a place of your choice on your next business trip?

Come on, you deserve it!

The best part about staying in Oakland 4 star hotels is that you’ll often be close to all the local sights and attractions. Whether you’re visiting the area for the first time or you’re back in town for more fun, a 4 star hotel is going to put you right in the heart of all the action.

Plus, you can rest easy knowing that you’re being well taken care of during your visit. Instead of worrying about where to eat or what to see, your friendly hotel staff will be happy to help you get whatever you need.

The best four star hotels in Oakland will also frequently include access to high-quality fitness centers and pools, so you’ll feel like you’re staying in an exclusive resort rather than a hotel. You won’t have any excuse for not keeping up with your workout routine!

If you’re looking for 4 star hotels in Oakland, you’ll find the most bang for your buck by booking your stay with Travelocity. Go explore a new city, and know you’re getting the best deal on a great hotel with the Travelocity Price Guarantee.

Recent Oakland hotel reviews by fellow wanderers

The Garrett Inn

5 out of 5

Posted 9 hours ago

Travelocity Verified Review

"Great rates and cute rooms . Friendly staff . Would highly recommend this place"

A verified traveler stayed at The Garrett Inn

Charming Dog Friendly Cottage w/ Dock & Fire Pit

5 out of 5

Posted 3 days ago

Travelocity Verified Review

"The Red Cottage was very clean and cozy. The views of the lake from inside the house were wonderful. The private dock area is a great place to lay in the sun and take a dip to cool off. The fire pit area was used every evening and was a very peaceful way to end the day. The outside grill was clean as was the patio area around it. There was a surprise when we pulled in though. The Red Cottage has a mini split AC unit which was not indicated on their page. The mini split had no issues keeping this beautiful little gem of a home cool for sleeping at night. I took my three adult daughters on a girls trip and this was our first time to Deep Creek Lake. We will be back. Overall a 5 star experience with Railey Vacations."

A verified traveler stayed at Charming Dog Friendly Cottage w/ Dock & Fire Pit

Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp

5 out of 5

Posted 4 days ago

Travelocity Verified Review

"Would absolutely recommend this house if you're considering a Deep Creek weekend. Check in process was extremely smooth, everything was clean and tidy when we arrived. Communication with the host was excellent from the time we booked until after we checked out. Our dog also loved it. I'm not entirely sure I've seen him more relaxed, although this was his first actual vacation that he's been on with us. Really easy walk to the lake side for fishing and swimming off the dock.If you have any questions about it, reach out. Terri was an excellent host."

A verified traveler stayed at Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp

Dog Friendly Cabin in the Woods, Hot Tub & Firepit

5 out of 5

Posted 4 days ago

Travelocity Verified Review

"This house and host is amazing!!! Communication was beyond what was expected, and the house was clean and comfortable! We stayed here for my son's baseball tournament and had a day off of playing. She offered ideas and even sent the link for things to do in the area. This place gets a 10 of 10 in my opinion. We definitely plan to come back with family!!!"

A verified traveler stayed at Dog Friendly Cabin in the Woods, Hot Tub & Firepit