Eastern Shore Adventure Vacations 2026

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Top Adventure vacation packages in Eastern Shore

Price found within the past 48 hours. Click for updated prices.

Hilton Ocean City Oceanfront Suites

Midtown Ocean City

$311

per person

Nov 6 - Nov 8

found 22 hours ago

Roundtrip flight included

Chicago (CHI) to Salisbury (SBY)

8.8/10 Excellent! (1,364 reviews)

Great

Reviewed on Aug 29, 2026

DoubleTree by Hilton Ocean City Oceanfront

Midtown Ocean City

$1,637

per person

Oct 2 - Oct 5

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)

9/10 Wonderful! (1,006 reviews)

Super location with access to the beach which was very convenient. Parking was a breeze. Will make this our every year visit.

Reviewed on Aug 29, 2026

Inn at Perry Cabin

Downtown St. Michaels

$1,983

per person

Oct 23 - Oct 26

found 22 hours ago

Roundtrip flight included

Philadelphia (PHL) to Salisbury (SBY)

9.6/10 Exceptional! (397 reviews)

Hyatt Regency Chesapeake Bay

$1,053

per person

Oct 23 - Oct 26

found 22 hours ago

Roundtrip flight included

Philadelphia (PHL) to Salisbury (SBY)

8.8/10 Excellent! (1,019 reviews)

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5* Adventure vacations in Eastern Shore

Price found within the past 48 hours. Click for updated prices.

Inn at Perry Cabin

Downtown St. Michaels

$1,983

per person

Oct 23 - Oct 26

found 22 hours ago

Roundtrip flight included

Philadelphia (PHL) to Salisbury (SBY)

9.6/10 Exceptional! (397 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Eastern Shore

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3 Night Adventure vacations in Eastern Shore

Price found within the past 48 hours. Click for updated prices.

Hyatt Regency Chesapeake Bay

$1,053

per person

Oct 23 - Oct 26

found 22 hours ago

Roundtrip flight included

Philadelphia (PHL) to Salisbury (SBY)

8.8/10 Excellent! (1,019 reviews)

DoubleTree by Hilton Ocean City Oceanfront

Midtown Ocean City

$1,637

per person

Oct 2 - Oct 5

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)

9/10 Wonderful! (1,006 reviews)

Super location with access to the beach which was very convenient. Parking was a breeze. Will make this our every year visit.

Reviewed on Aug 29, 2026

Inn at Perry Cabin

Downtown St. Michaels

$1,983

per person

Oct 23 - Oct 26

found 22 hours ago

Roundtrip flight included

Philadelphia (PHL) to Salisbury (SBY)

9.6/10 Exceptional! (397 reviews)

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See all available trips from Columbus to Eastern Shore

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4 Night Adventure vacations in Eastern Shore

Price found within the past 48 hours. Click for updated prices.

Microtel Inn & Suites by Wyndham Salisbury

$761

per person

Nov 17 - Nov 21

found 20 hours ago

Roundtrip non-stop flight included

Bridgetown (BGI) to Salisbury (SBY)

7.8/10 Good! (1,004 reviews)

Hampton Inn Salisbury

$1,568

per person

Sep 30 - Oct 4

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)

8.8/10 Excellent! (1,003 reviews)

Princess Royale Oceanfront Resort

North Ocean City

$1,263

per person

Oct 20 - Oct 24

found 1 day ago

Roundtrip non-stop flight included

Baltimore (BWI) to Salisbury (SBY)

8.8/10 Excellent! (2,673 reviews)

We really enjoyed our stay as a family of four with two young kids. The resort is located right on the beach and offers direct access, which was a huge plus for us. Our room appeared to have been recently renovated and was comfortable and well maintained. The staff were very friendly, welcoming, and accommodating throughout our stay. The main area that could use some updating is the pool and its surrounding area. It would also be great to see more activities and entertainment options for young children. Overall, the resort oceanfront view is beautiful, and we had a wonderful experience. We would definitely stay here again!

Reviewed on Aug 28, 2026

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How can I book the best Eastern Shore adventure trips?

Choose your own adventure in Eastern Shore, whether that’s a white-knuckle experience or a weekend walk. Read the reviews of the adventures that have gone before to be sure your chosen stay is your idea of fun.

How can I plan the perfect Eastern Shore family adventure vacation?

Adventure awaits when you select the family-friendly filter. There’s plenty of excitement for all ages in Eastern Shore. Just make sure to check your chosen escapade is within the realms of can-do for the whole clan and will have the whole team grinning.

Can I book all-inclusive Eastern Shore adventure vacation packages?

By refining your filters, you can explore all-amazing, all-adventurous, all-inclusive vacation packages. Amp up the extravagance with a few more filters too. Pick pristine pools, sensational spas, or wondrous waterparks for a sensational adventure getaway.

Why should I book a Eastern Shore adventure vacation for couples?

Book a Eastern Shore couples adventure vacation for the ultimate in romance and memory-making. Stunning scenery, heart-racing happenings, and the grandeur of the great outdoors—it’s the best way to bond.

How can I find the best deals on adventure packages in Eastern Shore?

It’s easy to unleash fabulously affordable adventures. Enter the dates for your caper, then sort your search results by price or deals.

Can I book an adventure vacation package in Eastern Shore with free cancellation and/or flexible dates?

Yes! When you’re searching for a great getaway, filter by payment option for free cancellation, so a change of plans won’t mess up your adventures. You’ll find buy now, pay later options, too, for full-on flexibility.

Why should I book a Eastern Shore adventure trip with Expedia?

Adventure, airfare, accommodation, ATOL protection, and activities—all on one site. And that’s just the benefits that begin with A.

Top Adventure Eastern Shore Hotels

Carousel Resort Hotel & Condominiums

11700 Coastal Hwy Ocean City MD

15 min drive from Ocean City Boardwalk

Book a stay at this beach hotel in Ocean City. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the helpful staff in our reviews. ...

Hyatt Regency Chesapeake Bay

100 Heron Blvd Cambridge MD

2 hours drive from Ocean City Boardwalk

Book a stay at this beach resort in Cambridge. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...

Hilton Garden Inn Ocean City Oceanfront

2800 Baltimore Ave Ocean City MD

28 min walk from Ocean City Boardwalk

Book a stay at this beach hotel in Ocean City. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...

See all 7,725 properties in Eastern Shore

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.