Oakland 4 Star Hotels In 2025

Check prices on hotels in Oakland

Featured Oakland 4 Star Hotels

Bear Hollow Lodge

20590 Garrett Highway, Oakland, MD

Strawberry Fields

10 Roman Ridge Road, Oakland, MD

Loft of Luxury

Oakland

Butterfly Retreat

1489 Mountainview Dr, Oakland, MD

Bears Lair

94 Lehman Lane, Oakland, MD

Paradise at Penn Cove

364 Penn Cove, Oakland, MD

Waves N' Moguls

104 Roman Ridge Road, Oakland, MD

Deja Blue

158 Silver Tree Lane, Oakland, MD

Lazy Bear Cove

91 Mary's Lane, Oakland, MD

See all 899 properties in Oakland

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.

Four Star Hotel Guide for Oakland, Maryland

Over the years, you’ve pinched pennies and stayed at the economy motels during your travels. However, now you’re nearing retirement or already basking in the work-free lifestyle, and you deserve to treat yourself to four-star hotels for ARRP members and seniors in Oakland, Maryland. Known for their extra perks, first-rate service, and fantastic locations, each of our 4-star AARP hotels in Oakland offers the ultimate experience for those looking for a bit of glitz and glamour on vacation.

Relax in your expertly designed room, kick back with around-the-clock room service, and indulge in the first-class amenities. Receive a good night’s sleep with the ultra-plush bedding, and freshen up in the morning with designer-inspired body products. It’s all at your fingertips, when you stay at one of the Oakland hotels with 4 stars for AARP members. Whether you’re traveling to celebrate the birth of your first grandchild or vacationing because you finally have the free time, let Expedia and AARP’s joined forces provide you with the best rates around on AARP hotels with four stars.