Eastern Shore Romantic Vacations

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Top Romantic vacation packages in Eastern Shore

Price found within the past 48 hours. Click for updated prices.
Hyatt Regency Chesapeake Bay
Inn at Perry Cabin
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5* Romantic vacations in Eastern Shore

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Inn at Perry Cabin
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3 Night Romantic vacations in Eastern Shore

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Hyatt Regency Chesapeake Bay
Inn at Perry Cabin
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4 Night Romantic vacations in Eastern Shore

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Grand Hotel Ocean City Oceanfront
Hilton Garden Inn Ocean City Oceanfront
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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 $1,316. 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?

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
Spa services, in-room massages, and luxurious surroundings await visiting couples at this adults-only hotel. The property also offers a lobby fireplace, champagne ...
9.4/10 Exceptional! (654 reviews)

Couples like: adults only property, onsite spa services, bar, champagne service

Travelers say...
Terrible

Reviewed on May 8, 2026

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
Enjoy a stay at this romantic condo, featuring in-room fireplaces and premium mattresses for couples to enjoy.
10/10 Exceptional! (121 reviews)

Couples like: adults only property, fireplace

Travelers say...
Emma was an amazing host. She kept in touch with us and recommended Fish Tales restaurant. The location is awesome, several amazing restaurants nearby. Loved the deck and decor. Ideal place for a romantic weekend away.

Reviewed on Sep 30, 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
Fall in love again at this upscale hotel. You and your special someone are sure to love the hot tub, spa, and ocean-view dining. You'll also appreciate the garden, ...
9.6/10 Exceptional! (385 reviews)

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

Travelers say...
We had yet another wonderful stay, great views, very comfortable. Some areas (primarily outside) would benefit from some paint.

Reviewed on May 14, 2026

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.

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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.