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

Find Romantic Hotels in Eastern Shore, MD from CA $102

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Eastern Shore Romantic Hotels

This weekend
Next weekend

Our top choices for Eastern Shore romantic hotels

1. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
4.0 star property
Cambridge
8.8 out of 10, Excellent, (1,009 reviews)
"Staff was perfect and the property is bigger than Rhode Island."
United States
John
The price is CA $201
CA $269 total
includes taxes & fees
Nov 23 - Nov 24
Hyatt Regency Chesapeake Bay

2. DoubleTree by Hilton Ocean City Oceanfront

DoubleTree by Hilton Ocean City Oceanfront
4.0 star property
Midtown Ocean City
9.0 out of 10, Wonderful, (1,000 reviews)
"Staff is always super nice and pleasant. I love the onsite parking available and the restaurant."
United States
SaVette
The price is CA $114
CA $127 total
includes taxes & fees
Nov 5 - Nov 6
DoubleTree by Hilton Ocean City Oceanfront

3. St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.0 out of 10, Very good, (1,004 reviews)
"Staff was very pleasant. Room was clean and a very nice Breakfast included."
United States
Dean
The price is CA $106
CA $117 total
includes taxes & fees
Nov 29 - Nov 30
St Michaels Inn

4. Holiday Inn & Suites Ocean City by IHG

Holiday Inn & Suites Ocean City by IHG
3.0 star property
Downtown Ocean City
9.4 out of 10, Exceptional, (1,457 reviews)
"Wonderful stay"
United States
Stephanie
The price is CA $126
CA $142 total
includes taxes & fees
Nov 29 - Nov 30
Holiday Inn & Suites Ocean City by IHG

5. Fenwick Inn

Fenwick Inn
3.0 star property
North Ocean City
8.8 out of 10, Excellent, (2,133 reviews)
"Very nice place"
United States
Shaun
The price is CA $87
CA $118 total
includes taxes & fees
Nov 11 - Nov 12
Fenwick Inn

6. Hilton Ocean City Oceanfront Suites

Hilton Ocean City Oceanfront Suites
4.0 star property
Midtown Ocean City
8.8 out of 10, Excellent, (1,352 reviews)
"This is my favorite place to stay on Ocean City Beach. The staff is always amazing. The hotel is always clean. I love the room service and self parking that is easy and convenient."
United States
SaVette
The price is CA $161
CA $180 total
includes taxes & fees
Nov 5 - Nov 6
Hilton Ocean City Oceanfront Suites

7. Ashore Oceanfront Hotel, Ocean City, a Tribute Portfolio Hotel

Ashore Oceanfront Hotel, Ocean City, a Tribute Portfolio Hotel
3.5 star property
North Ocean City
8.2 out of 10, Very good, (2,020 reviews)
"The staff were very helpful, welcoming, friendly, respectful and very professional."
United States
Michael
The price is CA $98
CA $110 total
includes taxes & fees
Nov 25 - Nov 26
Ashore Oceanfront Hotel, Ocean City, a Tribute Portfolio Hotel

8. The Tidewater Inn

The Tidewater Inn
3.0 star property
Easton
8.8 out of 10, Excellent, (935 reviews)
"We had a wonderful stay and thoroughly enjoyed our time in Easton!"
United States
Miriam
The price is CA $220
CA $242 total
includes taxes & fees
Nov 17 - Nov 18
The Tidewater Inn

9. Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (407 reviews)
"Fantastic place; one of those that you don’t want to leave the property until the very sad time to go. Lovely staff, all of them, amazing food."
United States
Virgilio
The price is CA $678
CA $746 total
includes taxes & fees
Nov 11 - Nov 12
Inn at Perry Cabin

10. Tru by Hilton Ocean City Bayside

Tru by Hilton Ocean City Bayside
2.5 star property
Midtown Ocean City
9.0 out of 10, Wonderful, (1,004 reviews)
"Breakfast and location"
United States
Steven
The price is CA $91
CA $102 total
includes taxes & fees
Nov 24 - Nov 25
Tru by Hilton Ocean City Bayside
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.

Find out more about Eastern Shore

Eastern Shore attractions for couples

The Eastern Shore of the United States is a paradise for discerning travellers seeking both adventure and relaxation. Begin your journey at Assateague Island National Seashore, where you can witness the famous wild ponies roaming freely along the pristine beaches, perfect for a family day out filled with picnics and seaside fun. Next, explore the charming town of St. Michaels, where you can indulge in fresh seafood at local eateries and visit the Chesapeake Bay Maritime Museum to learn about the area's rich maritime history. For a taste of nature, head to Blackwater National Wildlife Refuge, where you can enjoy birdwatching or kayaking, immersing yourself in the region’s stunning natural beauty. Don't miss the opportunity to stroll through the picturesque streets of Easton, known for its art galleries and boutique shops, offering unique finds and local crafts. After a day of exploration, consider staying at a waterfront hotel in Cambridge, where you can unwind with exceptional service and beautiful views of the Choptank River, ensuring a restful retreat after your adventures. Each of these experiences promises to be both memorable and enriching, catering to families and high-end travellers alike.

Top Eastern Shore Hotel Reviews

Explore a world of travel with Expedia