Eastern Shore Luxury Vacations 2026

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Top Luxury vacation packages in Eastern Shore

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

Hilton Ocean City Oceanfront Suites

Midtown Ocean City

$1,513

per person

Sep 8 - Sep 11

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Salisbury (SBY)

8.8/10 Excellent! (1,356 reviews)

Inn at Perry Cabin

Downtown St. Michaels

Save 100% on your flight

$2,715

per person

Oct 10 - Oct 14

found 13 hours ago

Roundtrip non-stop flight included

Cincinnati (CVG) to Salisbury (SBY)

9.6/10 Exceptional! (395 reviews)

Hyatt Regency Chesapeake Bay

$1,720

per person

Sep 8 - Sep 11

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Salisbury (SBY)

8.8/10 Excellent! (1,002 reviews)

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Reviewed on Aug 7, 2026

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5* Luxury 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

$2,715

per person

Oct 10 - Oct 14

found 13 hours ago

Roundtrip non-stop flight included

Cincinnati (CVG) to Salisbury (SBY)

9.6/10 Exceptional! (395 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Eastern Shore

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3 Night Luxury vacations in Eastern Shore

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

Hilton Ocean City Oceanfront Suites

Midtown Ocean City

$1,513

per person

Sep 8 - Sep 11

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Salisbury (SBY)

8.8/10 Excellent! (1,356 reviews)

Hyatt Regency Chesapeake Bay

$1,720

per person

Sep 8 - Sep 11

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Salisbury (SBY)

8.8/10 Excellent! (1,002 reviews)

Like like

Reviewed on Aug 7, 2026

Don't see what you're looking for?

See all available trips from Columbus to Eastern Shore

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4 Night Luxury vacations in Eastern Shore

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

Dunes Court

Midtown Ocean City

$1,014

per person

Sep 10 - Sep 14

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Salisbury (SBY)

8.4/10 Very Good! (1,018 reviews)

Our room looked clean at first glance, but the room smelled like straight up mold!! We made a complaint on the first night (we were the ones very nice and apologetic btw), and was told they would send house keeping over to check out the room and to possibly move us. That did not happen. Throughout our stay, we would keep our door open to try and ventilate the room. We planned on staying until 11am on check out day, but the smell of mold was so exasperating, we left at 7am instead. Now my family and I all have stuffing noses and itchy bodies from sleeping in mold air. The AC also didn’t work. We would have requested a refund, but the money wouldn’t have been processed right away, and we were already on a tight budget and wouldn’t have had the funds to books somewhere else. At least the pool was nice.

Reviewed on Aug 6, 2026

Princess Royale Oceanfront Resort

North Ocean City

$1,186

per person

Sep 10 - Sep 14

found 1 day ago

Roundtrip non-stop flight included

Cleveland (CLE) to Salisbury (SBY)

8.8/10 Excellent! (2,570 reviews)

The location on the beach was the best, easy walk. The indoor pool was nice but the temp in the pool needed to be higher because you couldn’t swim in it past 3 pm without it being freezing. The side corner balconies are very sketchy to sit on. The rooms themselves need a lot of maintenance done. Our towel rack was broken along with almost all of our closet doors and 2/3 of our TVs were broken. The place was clean and the service was great.

Reviewed on Aug 8, 2026

Inn at Perry Cabin

Downtown St. Michaels

Save 100% on your flight

$2,715

per person

Oct 10 - Oct 14

found 13 hours ago

Roundtrip non-stop flight included

Cincinnati (CVG) to Salisbury (SBY)

9.6/10 Exceptional! (395 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Eastern Shore

View all trips

What can I expect from a luxury Eastern Shore vacation?

Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Eastern Shore vacation. Sip handcrafted cocktails by an infinity pool, sink into bliss at a full-service spa with a massage cabana on the beach, and chat, cheers, and laugh through exquisite breakfasts, lunches, and dinners with spectacular views. 

How can I find all-inclusive luxury vacation packages in Eastern Shore?

By refining your filters, the most opulent all-inclusive vacation packages will appear before your eyes. Check the 5* filter to find truly sensational stays. You barely need to lift a finger. 

Can I book a cheap Eastern Shore luxury vacation?

Affordable luxury is only ever a few clicks away. Enter your travel dates and sort the grandiose getaways on offer by price to see the most fiscally friendly retreats first. Filter by budget, too, to find your perfect balance of luxury. Right now, luxury vacations start at $1,014. Prices and availability are subject to change. Additional terms may apply.

How can I book a luxury family vacation in Eastern Shore?

Tailor your luxury family escape by checking the filters that set the whole family’s hearts a-flutter. Whether that’s wet and wild water parks, heavenly hot tubs, or the kid-quieting magic of free Wi-Fi. 

Can I book a package in Eastern Shore with a luxury vacation home?

A private paradise is true luxury! Filter by property type for houses, villas, and apartments. For an amazingly affordable all-in-one luxury experience, book your accommodation, airfare, and car rental as a package.   

How can I find the best luxury vacation deals in Eastern Shore?

Find absolute delight in the dropdown! Simply sort your tempting search results by deals to find that lean-budget luxury. For a budget conscious stay, consider booking a stay away from big cities or outside the peak months.

Can I book a luxury holiday in Eastern Shore with free cancellation and/or flexible dates?

Freedom and flexibility are the greatest luxuries of all. Get both when you filter by payment option and book a trip with free cancellation or on a buy now, pay later plan. 

Why should I book my luxury trip to Eastern Shore with Expedia?

A luxurious trip follows a stress-free booking experience. Find, build, and book the most glorious of getaways in seconds—with ATOL protection for added peace of mind.

Top Luxury Eastern Shore Hotels

Inn at Perry Cabin

308 Watkins Ln St. Michaels MD

2 hours drive from Ocean City Boardwalk

Be treated to luxurious accommodations at Inn at Perry Cabin, where you can enjoy amenities like 24-hour room service, plush bedding, and more. Deluxe amenities ...

Inn at 202 Dover

202 East Dover Street Easton MD

2 hours drive from Ocean City Boardwalk

Pamper yourself with an extravagant stay at Inn at 202 Dover, where you'll find jetted bathtubs and pillowtop beds. Deluxe amenities at this inn include a restaurant, ...

Lighthouse Club Hotel

200 56th Street Ocean City MD

8 min drive from Ocean City Boardwalk

Pamper yourself with a luxury stay at Lighthouse Club Hotel, where you can enjoy amenities like Champagne service, massage services, and more. Notable amenities ...

9.4/10 Exceptional! (720 reviews)

"It was absolutely fabulous! The staff were amazing especially Christine and Frederica. They were so helpful. Our room was fantastic. Clean well stocked and the breakfast ready in your room was the best."

Reviewed on Aug 5, 2026

See all 7,937 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.