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.

DoubleTree by Hilton Ocean City Oceanfront

Midtown Ocean City

$640

per person

Nov 6 - Nov 9

found 20 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Salisbury (SBY)

9/10 Wonderful! (1,006 reviews)

Kitchen

Reviewed on Aug 25, 2026

Inn at Perry Cabin

Downtown St. Michaels

Save 100% on your flight

$759

per person

Oct 30 - Nov 1

found 17 hours ago

Roundtrip flight included

Denver (DEN) to Salisbury (SBY)

9.6/10 Exceptional! (397 reviews)

Hyatt Regency Chesapeake Bay

$1,456

per person

Sep 30 - Oct 4

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Salisbury (SBY)

8.8/10 Excellent! (1,019 reviews)

Hilton Ocean City Oceanfront Suites

Midtown Ocean City

$1,412

per person

Sep 25 - Sep 27

found 1 day ago

Roundtrip non-stop flight included

Akron (CAK) to Salisbury (SBY)

8.8/10 Excellent! (1,364 reviews)

Everything about our stay was accommodating. We needed extra towels, they provided it. We needed a rollout bed, it was there within minutes of us getting into our room. Staff was great, the rooms were clean, and the amenities were inviting! Overall great stay, great time!

Reviewed on Aug 24, 2026

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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

Save 100% on your flight

$759

per person

Oct 30 - Nov 1

found 17 hours ago

Roundtrip flight included

Denver (DEN) 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

View all trips

3 Night Adventure vacations in Eastern Shore

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

DoubleTree by Hilton Ocean City Oceanfront

Midtown Ocean City

$640

per person

Nov 6 - Nov 9

found 20 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Salisbury (SBY)

9/10 Wonderful! (1,006 reviews)

Kitchen

Reviewed on Aug 25, 2026

Inn at Perry Cabin

Downtown St. Michaels

$2,189

per person

Oct 2 - Oct 5

found 1 day ago

Roundtrip flight included

Philadelphia (PHL) to Salisbury (SBY)

9.6/10 Exceptional! (397 reviews)

Hilton Ocean City Oceanfront Suites

Midtown Ocean City

$1,341

per person

Oct 1 - Oct 4

found 19 hours ago

Roundtrip non-stop flight included

Providence (PVD) to Salisbury (SBY)

8.8/10 Excellent! (1,364 reviews)

Reviewed on Aug 24, 2026

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4 Night Adventure vacations in Eastern Shore

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

Harrison Hall Hotel

Downtown Ocean City

$1,175

per person

Sep 27 - Oct 1

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) to Salisbury (SBY)

7.6/10 Good! (1,016 reviews)

It was charming. Stafford was great Bathroom was ridiculously small.

Reviewed on Aug 26, 2026

Plim Plaza Hotel

Downtown Ocean City

$1,251

per person

Sep 27 - Oct 1

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) to Salisbury (SBY)

7.4/10 Good! (1,141 reviews)

Princess Royale Oceanfront Resort

North Ocean City

$1,269

per person

Sep 27 - Oct 1

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) to Salisbury (SBY)

8.8/10 Excellent! (2,606 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Eastern Shore

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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 ...

9/10 Wonderful! (1,423 reviews)

"We had a fantastic stay. The "we" was Me (Mom) and my two teenage daughters (13, 14) and our mid-size dog. We had a King, ocean front room with a balcony. The room was incredibly clean and felt very fresh and comfortable. It also had a pull out sofa which we used. The ocean view was spectacular and ..."

Reviewed on Aug 25, 2026

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.