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Oakland Vacations

Pack those stellar shades. We have Oakland vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Oakland – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Oakland vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Oakland

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Oakland vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Oakland well.

Top Hotel Deals

See all 289 Hotels in Oakland
Inn At Deep Creek

Inn At Deep Creek

19638 Garrett Hwy, Oakland
2.5 out of 5.0

Located in the heart of Oakland, this hotel is within 9 mi (15 km) of Wisp Resort, Swallow Falls State Park, and Thousand Acres Lakeside Golf Course. Adventure ...

The Garrett Inn

The Garrett Inn

17848 Garrett Highway, Oakland
2.5 out of 5.0

Situated in Oakland, this motel is 5.9 mi (9.5 km) from Swallow Falls State Park and within 12 mi (20 km) of Wisp Resort and Thousand Acres Lakeside Golf Course. ...

Oak Mar Motel

Oak Mar Motel

208 N 3rd Street, Oakland
2.0 out of 5.0

Situated in Oakland, this motel is within 12 mi (20 km) of Swallow Falls State Park, Cranesville Swamp Natural Area, and Cathedral State Park. Adventure Sports ...

Haley Farm Bed & Breakfast

Haley Farm Bed & Breakfast

16766 Garrett Highway, Oakland
3.0 out of 5.0

Situated in Oakland, this bed & breakfast is in the same area as Thousand Acres Lakeside Golf Course, Swallow Falls State Park, and Adventure Sports Center International. ...