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

$615

per person

Oct 29 - Nov 3

found 1 day ago

Roundtrip non-stop flight included

Lubbock (LBB) to Salisbury (SBY)

8.8/10 Excellent! (1,359 reviews)

The coffee machine inside the room just isn’t good..

Reviewed on Aug 11, 2026

Inn at Perry Cabin

Downtown St. Michaels

$3,371

per person

Oct 4 - Oct 10

found 1 day ago

Roundtrip non-stop flight included

Minneapolis (MSP) to Salisbury (SBY)

9.6/10 Exceptional! (395 reviews)

Hyatt Regency Chesapeake Bay

$1,441

per person

Sep 11 - Sep 14

found 1 day ago

Roundtrip non-stop flight included

Wilmington (ILM) to Salisbury (SBY)

8.8/10 Excellent! (1,002 reviews)

DoubleTree by Hilton Ocean City Oceanfront

Midtown Ocean City

$1,033

per person

Sep 12 - Sep 14

found 1 day ago

Roundtrip non-stop flight included

Hartford (HFD) to Salisbury (SBY)

9/10 Wonderful! (1,009 reviews)

Great location, pool was great, staff was super friendly. Very short walk to the beach. Room was great with a nice view of the ocean. Restaurant on site was very good. Staff at the pool bar was fantastic

Reviewed on Aug 9, 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

$3,371

per person

Oct 4 - Oct 10

found 1 day ago

Roundtrip non-stop flight included

Minneapolis (MSP) to Salisbury (SBY)

9.6/10 Exceptional! (395 reviews)

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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

$1,193

per person

Oct 1 - Oct 4

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Salisbury (SBY)

9/10 Wonderful! (1,009 reviews)

Reviewed on Aug 9, 2026

Hyatt Regency Chesapeake Bay

$1,441

per person

Sep 11 - Sep 14

found 1 day ago

Roundtrip non-stop flight included

Wilmington (ILM) to Salisbury (SBY)

8.8/10 Excellent! (1,002 reviews)

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4 Night Adventure vacations in Eastern Shore

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

Grand Hotel Ocean City Oceanfront

Downtown Ocean City

$1,168

per person

Sep 11 - Sep 15

found 8 hours ago

Roundtrip flight included

Sioux Falls (FSD) to Salisbury (SBY)

9/10 Wonderful! (3,727 reviews)

Horrible

Reviewed on Aug 12, 2026

Princess Royale Oceanfront Resort

North Ocean City

$1,179

per person

Sep 11 - Sep 15

found 8 hours ago

Roundtrip flight included

Sioux Falls (FSD) to Salisbury (SBY)

8.8/10 Excellent! (2,570 reviews)

Overall, we had a good time. Unfortunately, the jellyfish were at an all time high which isn't there fault but caused people to go to the pool and I think the pool could be updated a bit. Not enough chairs, and we never saw staff at the bar right by the pool until late at night. Our air conditioning was really loud but did work well. Room was clean but never enough towels for the five of us. Always had to request more especially with all the sand you bring in.

Reviewed on Aug 12, 2026

Hotel Monte Carlo Ocean City

Downtown Ocean City

$1,209

per person

Sep 11 - Sep 15

found 8 hours ago

Roundtrip flight included

Sioux Falls (FSD) to Salisbury (SBY)

7.8/10 Good! (1,013 reviews)

Hot tub jets didn't all operate, extremely long waiting for the elevator and the pools were small and shallow NOT MADE FOR ADULTS. Our room was near the ice machine so I couldn't rest because of the noise of the machine. Definitely not returning to Monte Carlo

Reviewed on Aug 11, 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 7,711 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.