
Eastern Shore Romantic Holidays
Book a Romantic Hotel + Flight or Car together to unlock savings
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Top Romantic Eastern Shore Hotels

Lighthouse Club Hotel
200 56th Street Ocean City MD
Stay at this luxury hotel in Ocean City. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff in their reviews. Popular attractions ...
9.4/10 Exceptional! (670 reviews)
Couples like: adults-only property, on-site spa services, bar, champagne service
Travellers say...
"The stay here was perfect. The hotel was very clean and quiet. The rooms are very spacious and welcoming. Having the balcony that overlooks the water was very peaceful. All the staff were very kind, helpful and nice. The stocked refrigerator was an added bonus. The cookies they put out each night ..."
Reviewed on 23 Jun 2026

Inn at Perry Cabin
308 Watkins Ln St. Michaels MD
Stay at this luxury hotel in St. Michaels. Enjoy free Wi-Fi, free valet parking and a full-service spa. Our guests praise the helpful staff in their reviews. ...
9.6/10 Exceptional! (390 reviews)
Couples like: full-service spa, restaurant with ocean view, Hot tub
Travellers say...
"It was a wonderful stay. The rooms were clean, the staff helpful and the food marvelous. I intend to visit again!"
Reviewed on 8 Jun 2026

Hyatt Regency Chesapeake Bay
100 Heron Blvd Cambridge MD
Stay at this beach resort in Cambridge. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Our guests praise the pool and the helpful staff in their reviews. ...
8.8/10 Excellent! (1,002 reviews)
Couples like: full-service spa, couples spa treatments, restaurant with ocean view, Hot tub
Travellers say...
"We loved staying here! Incredible staff!"
Reviewed on 22 Jun 2026
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
