Eastern Shore Romantic Vacations
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Top Romantic vacation packages in Eastern Shore
- Grand Hotel Ocean City Oceanfront
Dec 30 - Jan 3Grand Hotel Ocean City Oceanfront + Flight
Downtown Ocean City4 nights3.0 star property9.0/10 - Wonderful (4,012 reviews)"The room was nice and the beds were comfortable."Reviewed November 11, 2026Roundtrip • Miami (MIA) - Salisbury (SBY)MIA - SBY • 1 stop SBY - MIA • 1 stop$959$878found 1 day agoper traveler - Princess Royale Oceanfront Resort
Dec 30 - Jan 3Princess Royale Oceanfront Resort + Flight
North Ocean City4 nights3.0 star property8.8/10 - Excellent (2,895 reviews)Roundtrip • Miami (MIA) - Salisbury (SBY)MIA - SBY • 1 stop SBY - MIA • 1 stop$1,094$1,000found 1 day agoper traveler - Ashore Oceanfront Hotel, Ocean City, a Tribute Portfolio Hotel
Dec 30 - Jan 3Ashore Oceanfront Hotel, Ocean City, a Tribute Portfolio Hotel + Flight
North Ocean City4 nights3.5 star property8.2/10 - Very good (2,023 reviews)"The room was clean, however, I was disappointed with several aspects of my stay. When booking, the hotel advertised availability for “oceanfront rooms.” I later discovered that the hotel does not actually offer true oceanfront rooms, only partial ocean views. I found this very misleading, and it was disappointing to arrive expecting an oceanfront room only to be given a partial view. I visited during the off-season and noticed that the fire pit had an on/off switch. When I asked the staff if I..."Reviewed November 9, 2026Roundtrip • Miami (MIA) - Salisbury (SBY)MIA - SBY • 1 stop SBY - MIA • 1 stop$1,750$1,619found 1 day agoper traveler - Hyatt Regency Chesapeake Bay
Dec 30 - Jan 3Hyatt Regency Chesapeake Bay + Flight
Cambridge4 nights4.0 star property8.8/10 - Excellent (1,006 reviews)Roundtrip • Miami (MIA) - Salisbury (SBY)MIA - SBY • 1 stop SBY - MIA • 1 stop$1,308$1,224found 1 day agoper traveler - Holiday Inn Ocean City by IHG
Dec 30 - Jan 3Holiday Inn Ocean City by IHG + Flight
North Ocean City4 nights3.0 star property8.8/10 - Excellent (1,006 reviews)Roundtrip • Miami (MIA) - Salisbury (SBY)MIA - SBY • 1 stop SBY - MIA • 1 stop$914$885found 1 day agoper traveler
Discover the most popular places to visit in Eastern Shore
What to do in Eastern Shore
Funfull Family Package Delmarva
Top Romantic Eastern Shore Hotels
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHG"Hot cereal instead of instant"
Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & Marina
"They double booked my room and did not give me any options so was basically homeless"
Comfort Inn Ocean City Boardwalk
Comfort Inn Ocean City Boardwalk
Home2 Suites By Hilton Salisbury Fruitland
Home2 Suites By Hilton Salisbury Fruitland
"It's not unique to this property but the staff is wonderful. Very pleasant and customer oriented."
Fairfield Inn & Suites by Marriott Easton
Fairfield Inn & Suites by Marriott Easton
Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island Marina"Coffee in the breakfast area was terrible. Weak and watery. Thta' might seem like a minor factor. but for those of us who appreciate a good, strong cup of coffee, it's a problem."
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 $878. 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?