Eastern Shore Luxury Holidays

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All you need to know about luxury holidays in Eastern Shore

What can I expect from a luxury Eastern Shore holiday?

Luxury on holiday is all about relaxing and feeling good. Whether you choose a sumptuous spa, Michelin-starred restaurant or super-king bed is your call. Use our amenities filters to find the things that tick all your boxes.

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

Tick the all-inclusive and 5-star filters to find the crème de la crème of Eastern Shore holidays. With everything included in the package price, you can drink and dine to your heart’s content, without worrying about that bill at the end.

Can I book a cheap luxury holiday to Eastern Shore?

A luxury holiday doesn’t have to break the bank. Travel out of peak season, choose a hotel or resort a little way out or go for a last-minute getaway and you’ll find some cracking deals. Sort by price to find luxury holidays to Eastern Shore starting at . Prices and availability are subject to change. Additional terms may apply.

Are there luxury spa holidays in Eastern Shore?

For sunset massages on the shoreline and view-filled saunas, use our spa filter to find your ideal Eastern Shore spa hotel. Book a whole weekend soaking away your stresses, or hop into the spa after the beach, some golf or a local advent-ahhhh.

What should I look for when booking a luxury family holiday in Eastern Shore?

Luxury isn’t just for adults. Those little touches designed for little people make a family holiday genuinely stress free … which is the greatest luxury of all. Look for spacious suites, pools toddlers can splash in, and breakfast buffets with waffles, pancakes and Nutella galore.

Can I book luxury last-minute holidays to Eastern Shore?

You can wangle a top-notch luxury holiday in Eastern Shore for a fraction of the normal price by booking last minute. Just enter your dates and see what’s available – if you’re flexible ... even better!

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

If you’re splashing out on a luxury holiday, make sure your money is safe by booking with free cancellation. Just use the fully refundable filter and make sure you read all the terms and conditions.

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

Nobody does luxury quite like Expedia. With so many gorgeous properties in Eastern Shore to choose from, as well as access to first-class flight deals and hire cars with horsepower, there’s no better place to book.

Top Luxury Eastern Shore Hotels

Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln, St. Michaels, MD
  • 2 hours drive from Ocean City Boardwalk
Stay at this luxury hotel in St. Michaels. Enjoy free Wi-Fi, free valet parking and a full-service spa. Our guests praise the helpful staff in their reviews. ...
9.4/10 Exceptional! (361 reviews)
Lived up to its Reputation
"My wife and I recently stayed here to celebrate a milestone birthday. It certainly lived up to the hype and was one do the nicer places we have ever stayed."

Reviewed on 25 Aug 2025

Inn at Perry Cabin
Inn at 202 Dover

Inn at 202 Dover

5 out of 5
202 East Dover Street, Easton, MD
  • 2 hours drive from Ocean City Boardwalk
Stay at this 5-star luxury inn in Easton. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Avalon Theatre and Customs House are located ...
Very romantic and beautiful Inn!
"We stayed in the French Room at the Inn at 202Dover in Easton, MD. We were welcomed by the manager, Vincent. The room was just as beautiful as it looked in the photos! The whole inn is a gem! The only thing I didn't end up trying was the hydrojet massage bathtub. There were directions in the guest ..."

Reviewed on 28 Apr 2019

Inn at 202 Dover
Lighthouse Club Hotel

Lighthouse Club Hotel

3 out of 5
200 56th Street, Ocean City, MD
  • 8 min drive from Ocean City Boardwalk
Stay at this 3-star luxury hotel in Ocean City. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. Popular ...
9.4/10 Exceptional! (605 reviews)
Looking forward to returning
"Excellent service and stay!! Looking forward to returning Ocean City Maryland, and will definitely stay at this location again."

Reviewed on 20 Aug 2025

Lighthouse Club Hotel
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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.