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

Eastern Shore Romantic Vacations

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  • Top Romantic vacation packages in Eastern Shore

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

    Ocean City Boardwalk

    Rating: 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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    A coastal cityscape with a sandy beach, ocean waves, and high-rise buildings.

    Ocean City Beach

    Rating: 9.2/10 (10,973 reviews)

    This classic 10-mile stretch of Atlantic shoreline pairs pristine sand with a vibrant, attraction-filled boardwalk. Enjoy free beach access year-round, with seasonal festivals adding extra charm to your coastal getaway.

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    A stone wall with the text "Roland E. Powell Convention Center" and a landscaped area with trees and shrubs.

    Roland E. Powell Convention Center

    Rating: 8.0/10 (2,358 reviews)

    This modern bayfront venue hosts Ocean City's premier events, from trade shows to concerts. Enjoy panoramic water views while attending diverse exhibitions in its state-of-the-art facilities.

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    A carousel, a large statue, and a building with a neon sign.

    Jolly Roger Amusement Park

    Rating: 8.2/10 (3,806 reviews)

    This dual-location amusement park features ocean-view rides at the Pier and thrilling water attractions at 30th Street. Enjoy illuminated attractions and panoramic Atlantic views from the Giant Wheel.

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    A wooden boardwalk by a body of water with binoculars and a bench.

    Inlet Park

    Rating: 8.6/10 (1,457 reviews)

    Gaze across the Atlantic toward Assateague Island from this peaceful coastal viewpoint. The park's wooden "Whispering Giant" sculpture honors Native American heritage while offering wildlife spotting.

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    A vibrant amusement park with a Ferris wheel, a prize factory, and various rides and attractions.

    Jolly Roger at the Pier

    Rating: 8.4/10 (2,874 reviews)

    This lively boardwalk amusement park dazzles with iconic rides like the Giant Wheel and Looping Star Roller Coaster. Evening visits offer magical views when colorful lights illuminate against the Atlantic sky.

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    Salisbury University

    Rating: 8.4/10 (452 reviews)

    Salisbury University's picturesque campus blends historic and modern architecture. Explore the Patricia R. Guerrieri Academic Commons for panoramic views and check the event calendar for cultural performances.

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    What to do in Eastern Shore

    Funfull Family Package Delmarva

    Funfull Family Package Delmarva

    $700

    per adult

    0% of travelers recommend

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    Top Romantic Eastern Shore Hotels

    Hyatt Regency Chesapeake Bay

    A resort with a large pool, outdoor seating, and a view of the sea.
    • Address: 100 Heron Blvd, Cambridge, MD, 21613, US
    • Location: 12.2 mi from Eastern Shore
    • Star rating: 4/5
    • Guest rating: 8.8/10 (Excellent, 1001 reviews)
    • Price: $194 nightly, $221 total, Nov 22 - Nov 23, Total with taxes and fees, for Top Romantic Eastern Shore Hotels

    St Michaels Inn

    A rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.
    • Address: 1228 S Talbot Street, St. Michaels, MD, 21663, US
    • Location: 20.2 mi from Eastern Shore
    • Star rating: 2.5/5
    • Guest rating: 8/10 (Very good, 1003 reviews)
    • Price: $87 nightly, $96 total, Nov 18 - Nov 19, Total with taxes and fees, for Top Romantic Eastern Shore Hotels

    DoubleTree by Hilton Ocean City Oceanfront

    A balcony with a view of the beach and ocean.
    • Address: 3301 Atlantic Ave, Ocean City, MD, 21842, US
    • Location: 47.3 mi from Eastern Shore
    • Star rating: 4/5
    • Guest rating: 9/10 (Wonderful, 1003 reviews)
    • Price: $81 nightly, $91 total, Nov 22 - Nov 23, Total with taxes and fees, for Top Romantic Eastern Shore Hotels

    Holiday Inn & Suites Ocean City by IHG

    A clear pool with palm trees, lounge chairs, and umbrellas.
    • Address: 1701 Atlantic Avenue, Ocean City, MD, 21842, US
    • Location: 47.5 mi from Eastern Shore
    • Star rating: 3/5
    • Guest rating: 9.4/10 (Exceptional, 1463 reviews)
    • Price: $90 nightly, $101 total, Dec 13 - Dec 14, Total with taxes and fees, for Top Romantic Eastern Shore Hotels

    Fenwick Inn

    A modern house with a glass door entrance, outdoor seating area with chairs, and a small table.
    • Address: 13801 Coastal Highway, Ocean City, MD, 21842, US
    • Location: 46 mi from Eastern Shore
    • Star rating: 3/5
    • Guest rating: 9/10 (Wonderful, 2131 reviews)
    • Price: $75 nightly, $85 total, Nov 30 - Dec 1, Total with taxes and fees, for Top Romantic Eastern Shore Hotels
    • Review: Great place

    Residence Inn by Marriott Ocean City

    A balcony with a view of the sea, a pool, and a row of chairs.
    • Address: 300 Seabay Lane, Ocean City, MD, 21842, US
    • Location: 46.7 mi from Eastern Shore
    • Star rating: 3/5
    • Guest rating: 9/10 (Wonderful, 1003 reviews)
    • Price: $82 nightly, $92 total, Nov 19 - Nov 20, Total with taxes and fees, for Top Romantic Eastern Shore Hotels

    The Tidewater Inn

    A large, stately house with a grand entrance, multiple windows, and a symmetrical facade.
    • Address: 101 E Dover St, Easton, MD, 21601, US
    • Location: 14 mi from Eastern Shore
    • Star rating: 3/5
    • Guest rating: 8.8/10 (Excellent, 939 reviews)
    • Price: $176 nightly, $193 total, Nov 16 - Nov 17, Total with taxes and fees, for Top Romantic Eastern Shore Hotels

    Hilton Ocean City Oceanfront Suites

    A resort pool area with lounge chairs, palm trees, and a boat-shaped water feature.
    • Address: 3200 N Baltimore Ave, Ocean City, MD, 21842, US
    • Location: 47.4 mi from Eastern Shore
    • Star rating: 4/5
    • Guest rating: 8.8/10 (Excellent, 1362 reviews)
    • Price: $115 nightly, $129 total, Nov 22 - Nov 23, Total with taxes and fees, for Top Romantic Eastern Shore Hotels
    • Review: The hotel was in a great location. Suites are very large and comfortable. Pool was large and very nice. Staff was very helpful. Directly on the oceanfront and only a few blocks from the boardwalk. Sofa bed was not comfortable for an adult. Rollaway was the way to go for one extra person. We would definitely stay again. We rented 4 suitesclosr together for our family celebration and it was perfect. Only downside was parking at $10 a day.

    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 $507. 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?

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