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Eastern Shore Vacations

Pack those stellar shades. We have Eastern Shore 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 Eastern Shore – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Eastern Shore 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 Eastern Shore

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 Eastern Shore 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 Eastern Shore well.

Eastern Shore Flight + Hotel packages

Top Hotel Deals

See all 763 Hotels in Eastern Shore
Days Inn Salisbury

Days Inn Salisbury

2525 N Salisbury Blvd, Salisbury
2.5 out of 5.0

Situated in Salisbury, this motel is 0.4 mi (0.7 km) from Centre at Salisbury and 3.1 mi (5 km) from Poplar Hill Mansion. Salisbury University and Coco's Funhouse ...

$30

$30
Grand Hotel & Spa

Grand Hotel & Spa

2100 N Baltimore Ave, Ocean City
3.5 out of 5.0

Located on the Ocean City Boardwalk, The Grand Hotel & Spa offers beach access and is within 2 miles of Roland E Powell Convention Center.

$54

$54
Dunes Manor Hotel & Suites

Dunes Manor Hotel & Suites

2800 Baltimore Ave, Ocean City
3.5 out of 5.0

Located in Midtown Ocean City, this resort is within a 15-minute walk of Ember's Island Miniature Golf and Planet Maze. Jolly Roger Amusement Park and Roland ...

$56

$56
Hilton Ocean City Oceanfront Suites

Hilton Ocean City Oceanfront Suites

3200 N Baltimore Ave, Ocean City
4.5 out of 5.0

Located in Midtown Ocean City, this beachfront hotel is in the city center and within a 15-minute walk of Planet Maze, Ember's Island Miniature Golf, and Roland ...

$95

$95
Microtel Inn & Suites by Wyndham Ocean City

Microtel Inn & Suites by Wyndham Ocean City

12536 Ocean Gateway, Ocean City
3.0 out of 5.0

Located in West Ocean City, this hotel is within a 10-minute walk of Grand Prix Amusements, Baja Amusements, and Wheels of Yesterday. Tanger Outlet Center and ...

$49

$49
Holiday Inn Ocean City

Holiday Inn Ocean City

6600 Coastal Hwy, Ocean City
3.5 out of 5.0

Located in Ocean City, this beachfront hotel is in the city center and within 2 mi (3 km) of Maui Golf, Ocean Plaza Mall Shopping Center, and Roland E. Powell ...

$50

$50
Crystal Beach Hotel

Crystal Beach Hotel

2500 N. Baltimore Ave., Ocean City
3.0 out of 5.0

Nestled on the beach, this Ocean City hotel is within a 15-minute walk of Ember's Island Miniature Golf and Planet Maze. Jolly Roger Amusement Park and Roland ...

Fenwick Inn

Fenwick Inn

13801 Coastal Highway, Ocean City
2.5 out of 5.0

Located in North Ocean City, this hotel is within a 15-minute walk of Lost Treasure Golf, Golf Down Under, and Fenwick Island Lighthouse. Transpeninsular Line ...

$50

$50
Carousel Resort Hotel & Condominiums

Carousel Resort Hotel & Condominiums

11700 Coastal Hwy, Ocean City
3.5 out of 5.0

Offering easy access to the city's many shops and restaurants, the waterfront 22-story Carousel Resort Hotel is five miles from the boardwalk, Ocean City Factory ...

$59

$59
Tidelands Caribbean Hotel and Suites

Tidelands Caribbean Hotel and Suites

5th Street on the Boardwalk Ocean City, Ocean City
2.5 out of 5.0

Situated on the beach, this hotel is within a 10-minute walk of Ocean Bowl Skate Park, Midway Shopping Center, and Ripley's Believe It or Not Museum. Jolly Roger ...

$359

$359

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.