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

    Cambria Hotel Ocean City - Bayfront

    A balcony with white railings and orange chairs, overlooking a body of water and a distant shoreline.
    • Address: 13 SAINT LOUIS AVE, Ocean City, MD, 21842, US
    • Location: 47.4 mi from Eastern Shore
    • Star rating: 3/5
    • Guest rating: 9.2/10 (Wonderful, 1000 reviews)
    • Price: $81 nightly, $91 total, Dec 7 - Dec 8, Total with taxes and fees, for Top Romantic Eastern Shore Hotels
    • Review: The room was gorgeous

    Hyatt Place Kent Narrows & Marina

    A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.
    • Address: 3028 KENT NARROW WAY S, Grasonville, MD, 21638, US
    • Location: 29.7 mi from Eastern Shore
    • Star rating: 3/5
    • Guest rating: 9.4/10 (Exceptional, 862 reviews)
    • Price: $134 nightly, $149 total, Nov 18 - Nov 19, Total with taxes and fees, for Top Romantic Eastern Shore Hotels
    • Review: We stayed in a room with two queens and a balcony facing the water. Gorgeous view. Room was exceptionally clean, spacious and had everything we needed. Staff was very friendly when we arrived at check in, personable and informative. The breakfast buffet was massive, had many options. Next door to the hotel, was a delicious restaurant, the Fisherman's Inn. Will definitely stay again!

    Hampton Inn & Suites Ocean City/Bayfront-Convention Center

    A pool area with lounge chairs, a hot tub, and a view of the ocean.
    • Address: 4301 Coastal Hwy, Ocean City, MD, 21842, US
    • Location: 47.1 mi from Eastern Shore
    • Star rating: 2.5/5
    • Guest rating: 8.8/10 (Excellent, 1000 reviews)
    • Price: $59 nightly, $66 total, Dec 10 - Dec 11, Total with taxes and fees, for 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: $189 nightly, $215 total, Dec 16 - Dec 17, Total with taxes and fees, for Top Romantic Eastern Shore Hotels

    Grand Hotel Ocean City Oceanfront

    A wooden boardwalk leading to a beachfront hotel with multiple balconies and a clear view of the ocean.
    • Address: 2100 N Baltimore Ave, Ocean City, MD, 21842, US
    • Location: 47.5 mi from Eastern Shore
    • Star rating: 3/5
    • Guest rating: 9/10 (Wonderful, 4015 reviews)
    • Price: $59 nightly, $66 total, Nov 16 - Nov 17, Total with taxes and fees, for Top Romantic Eastern Shore Hotels
    • Review: Spacious room, friendly staff, great views and right on the OC Boardwalk. Would recommend.

    St Michaels Inn

    A reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.
    • 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, 1006 reviews)
    • Price: $87 nightly, $96 total, Dec 16 - Dec 17, Total with taxes and fees, for Top Romantic Eastern Shore Hotels

    Holiday Inn Ocean City by IHG

    A resort with a swimming pool, sun loungers, and a view of the ocean.
    • Address: 6600 Coastal Hwy, Ocean City, MD, 21842, US
    • Location: 46.9 mi from Eastern Shore
    • Star rating: 3/5
    • Guest rating: 8.8/10 (Excellent, 1001 reviews)
    • Price: $61 nightly, $68 total, Dec 14 - Dec 15, Total with taxes and fees, for Top Romantic Eastern Shore Hotels

    DoubleTree by Hilton Ocean City Oceanfront

    A balcony with wicker furniture and a table, overlooking a beach with umbrellas and people.
    • 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

    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 $213. 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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