Eastern Maryland Luxury Holidays

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All you need to know about luxury holidays in Eastern Maryland

What can I expect from a luxury Eastern Maryland 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 Maryland?

Tick the all-inclusive and 5-star filters to find the crème de la crème of Eastern Maryland 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 Maryland?

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 Maryland starting at . Prices and availability are subject to change. Additional terms may apply.

Are there luxury spa holidays in Eastern Maryland?

For sunset massages on the shoreline and view-filled saunas, use our spa filter to find your ideal Eastern Maryland 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 Maryland?

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 Maryland?

You can wangle a top-notch luxury holiday in Eastern Maryland 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 Maryland 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 Maryland with Expedia?

Nobody does luxury quite like Expedia. With so many gorgeous properties in Eastern Maryland 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 Maryland 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! (352 reviews)
"We loved our stay at the Inn at Perry Cabin! It was so beautiful, quiet, clean, cute, and spacious. The restaurants in the resort are amazing and the food was outstanding. Everyone is so welcoming and kind. There are great amenities to offer. We enjoyed the pool. There is a nice downtown area with ..."

Reviewed on 3 Jul 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! (550 reviews)
"I love this please go is beautiful place I want to go again I share the lighthouse club with my friend and family please go"

Reviewed on 29 Jun 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.