Eastern Shore Luxury Vacations 2026

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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 ...

9.6/10 Exceptional! (405 reviews)

"Outstanding experience in every way. Staff was superior — everyone greeted us by name and was eager to ensure we had everything we needed. Meals at Stars were excellent — and the gorgeous views of the water and property enhanced the dining experience. The lit firepits and comfy seating outside were ..."

Reviewed on 2026/9/29

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! (766 reviews)

"Hotel was outstanding and the staff were extremely helpful!"

Reviewed on 2026/9/29

See all 7,765 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.