Eastern Shore Romantic Holidays

Book a Romantic Hotel + Flight or Car together to unlock savings

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    Better together
    Save up to £335 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

How to find a romantic Eastern Shore holiday

How can I find the best Eastern Shore vacation packages for couples?

Use our easy-to-use holiday search tools to plan your most-romantic getaway to Eastern Shore. Choose a hotel suite with an on-trend bathtub with a big view. Choose a stylish hire car with the top down to woo your heart. Choose candlelit cocktails on the shoreline, a horse ride by moonlight or a dolled-up night at the casino.

Can I book cheap Eastern Shore romantic holidays for two?

Get wallet-friendly away-from-it-all romantic accommodation at Expedia, so you have more kitty to spend on romantic activities. We have cheap romantic holidays to Eastern Shore that start from . Prices and availability are subject to change. Additional terms may apply.

What should I think about when booking a Eastern Shore romantic getaway?

The most romantic holidays are about building memories, about dancing and dining and keeping the spark alive. These are moments to level up the luxury – use the star filter to find the best of the best, maybe even tick the business-class flights filter to make the journey part of the adventure.

What should I look for in a luxury romantic holiday to Eastern Shore?

Spoil yourselves with a few luxuries on your romantic trip away. You can use our filters to add that extra touch of romance to your holiday: glamorous spas, divine private dining, exquisite room service.

Can I book a romantic hot-tub holiday in Eastern Shore?

What’s more romantic than a hot tub under the stars, together? Add a glass of fizz, a gorgeous view and Cupid’s arrow and you’re good. To find accommodation with bubbles, use our dedicated hot-tub filter.

How can I find romantic holidays for couples in Eastern Shore that are all inclusive?

Enjoying an all-inclusive holiday means you can really indulge your appetites together – with the promise of no awkward arguments about splitting the bill. Simply use our all-inclusive filter to see what romantic options are available.

Can I book a romantic trip to Eastern Shore with free cancellation and/or flexible dates?

Even the best laid plans fall through sometimes. Make sure you’re not caught out – using our filters to find free cancellation accommodation. Just make sure you check the all-important small print.

Why should I book my Eastern Shore romantic holiday with Expedia?

At Expedia, we know the not-so-secret ingredients to the perfect romantic holiday. Our handy filters help you search a huge range of options and book a holiday that gets your hearts racing.

Top Romantic Eastern Shore Hotels

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)

Couples like: adults-only property, bar

Travellers say...
"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
Romantic Beach Getaway For 2 In Ocean City MD
Romantic Beach Getaway For 2 In Ocean City MD
Ocean City, MD
  • 22 min walk from Ocean City Boardwalk
Stay at this condo in Ocean City. Enjoy a water park, laundry facilities and balconies. Popular attractions Ocean City Boardwalk and Ocean City Beach are located ...
9.8/10 Exceptional! (110 reviews)

Couples like: adults-only property, fireplace

Nice place
"The area was great. Close to the beach."

Reviewed on 30 Jun 2025

Romantic Beach Getaway For 2 In Ocean City MD
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)

Couples like: full-service spa, restaurant with ocean view, Hot tub

Travellers say...
"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
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.

More holidays you might like

* 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.