A marina with numerous boats docked at wooden piers under a clear sky.

Eastern Shore Romantic Vacations

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Discover the most popular places to visit in Eastern Shore

A boardwalk entrance with a sign reading "Boardwalk Maryland" and two lighthouse-style structures.

Ocean City Boardwalk

9.0/10 (11,302 reviews)
This historic three-mile boardwalk has delighted visitors with ocean views and carnival charm since 1902. Savor local favorites like Thrasher's French Fries while exploring vintage amusement rides at Trimper's.
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Top Romantic Eastern Shore Hotels

A gazebo with a view of a lake at dusk.

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
47.8 km from Eastern Shore
9.2 out of 10, Wonderful, (1,002 reviews)
"Staff was very friendly."
The price is ₩135,735
₩150,666 total
includes taxes & fees
Nov 23 - Nov 24
Holiday Inn Express Annapolis East-Kent Island by IHG
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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How to find a romantic Eastern Shore vacation

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

To win over the love of your life, first choose where and when you want to bring the romance. Now flirt with the filters to add ocean views, spa, pools, and anything else that gets your heart racing.

How can I find cheap Eastern Shore romantic packages for two?

For dollar-friendly delights, sort your search results by price or deals. You can also filter by budget to find romantic retreats at prices you’ll love. For an affordable and alluring adventure, try self-catering.

How can I plan a great romantic trip to Eastern Shore?

Find what fills you with joy and dive right in, whether you thrill in a little adventure or lust for long lazy days by the pool, handcrafted cocktails in hand. Fire cupid’s arrow at our filters and build your dream trip for two.

How much is a trip for two to Eastern Shore?

Put a price on love with stunning deals for duos starting at just . Prices and availability are subject to change. Additional terms may apply.

Can I book Eastern Shore spa packages for couples?

Check the filter box for a seductive stay at a spa. Sort your results by price, deals, rating, and more to guarantee the perfect match.

How can I book romantic weekend getaway packages in Eastern Shore?

To book a loved-up break in Eastern Shore, enter your travel dates and sort by price, deals, rating—whatever matters most to you and your partner. Now, you can add some adult-only amenities, like a hot tub or full-service spa for total R, R, & R (that’s romance, rest, and recuperation).

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

The course of true love should always run smooth, but we get that there are hiccups. So, filter by payment option to search for romantic stays with free cancellation and buy now, pay later options.

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

If you’ve only got eyes for excellent escapes, book your loved-up break with Expedia. Fling the filters to find accommodation you’ll adore. And what’s more attractive than ATOL protection?