Eastern Shore Hotel Guide - Romantic Hotels in Eastern Shore, Maryland

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Our top choices for Eastern Shore romantic hotels

Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (58 reviews)
"We got every year and stay here, it’s great! "
United States
Margaret H.
The price is €220
includes taxes & fees
13 Apr - 14 Apr
Deal Island Bay Cottage

Top-Rated Luxury Oceanfrt Condo Spectacular Views-Outstanding Reviews

Top-Rated Luxury Oceanfrt Condo Spectacular Views-Outstanding Reviews
North Ocean City
9.6 out of 10, Exceptional, (93 reviews)
"Views of both sunrise over the ocean and sunset over the bay, beautiful! Enjoyed the indoor pool, basketball court, game room, workout room and walks on the beach."
United States
Helen V.
The price is €393
includes taxes & fees
13 Apr - 14 Apr
Top-Rated Luxury Oceanfrt Condo Spectacular Views-Outstanding Reviews

BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen

BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen
Berlin
9.8 out of 10, Exceptional, (100 reviews)
"Property was perfect for us and our dogs."
United States
Jeffrey B.
The price is €273
includes taxes & fees
1 May - 2 May
BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen

5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown
Perryville
9.8 out of 10, Exceptional, (150 reviews)
"Magical and made tons of family wedding memories. What a perfect house on the river!! We will be booking again"
United States
Mary D.
The price is €441
includes taxes & fees
14 Apr - 15 Apr
5-bedroom vacation home 5 minutes from historic Charlestown

Beach Paradise III - DOWNTOWN OCEANVIEW Luxury Townhome-Steps to Beach&Boardwalk

Beach Paradise III - DOWNTOWN OCEANVIEW Luxury Townhome-Steps to Beach&Boardwalk
Downtown Ocean City
9.6 out of 10, Exceptional, (82 reviews)
"Beautiful house in an awesome area! We had a fairly large group & were all very pleased with our stay. 10/10 would recommend!!"
United States
Alexis C.
Beach Paradise III - DOWNTOWN OCEANVIEW Luxury Townhome-Steps to Beach&Boardwalk

BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!

BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!
North Ocean City
9.8 out of 10, Exceptional, (141 reviews)
"The home was beautifully decorated for the holidays. Everything was just as described and Kim was an excellent host. "
United States
Pamela M.
The price is €310
includes taxes & fees
19 Apr - 20 Apr
BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!

BEACH PARADISE V - 4BR, 3.5BA NEW GARAGE Townhouse in PRIME MIDTOWN OC!

BEACH PARADISE V - 4BR, 3.5BA NEW GARAGE Townhouse in PRIME MIDTOWN OC!
North Ocean City
9.6 out of 10, Exceptional, (68 reviews)
"The place was beautiful , convenient to walk around to the beach and the stores "
United States
Theresa K.
The price is €300
includes taxes & fees
22 Apr - 23 Apr
BEACH PARADISE V - 4BR, 3.5BA NEW GARAGE Townhouse in PRIME MIDTOWN OC!

Mid Town OceanSide/Block 46th St. Sleeps 5 Location, Location, Location!

Mid Town OceanSide/Block 46th St. Sleeps 5 Location, Location, Location!
Midtown Ocean City
9.0 out of 10, Wonderful, (123 reviews)
"Perfect location. Clean and safe. Thanks for a great stay! "
United States
Kelly G.
The price is €289
includes taxes & fees
13 Apr - 14 Apr
Mid Town OceanSide/Block 46th St. Sleeps 5 Location, Location, Location!

Romantic Ocean Block Retreat – Steps to Beach, Ocean block Condo 100 steps from the beach

Romantic Ocean Block Retreat – Steps to Beach, Ocean block Condo 100 steps from the beach
Midtown Ocean City
9.6 out of 10, Exceptional, (4 reviews)
"Great rental with view of both Bay and Ocean from top seating area. We enjoyed our stay and would definitely stay again. Very short walk to beach and had everything we needed to feel at home. Great decor and furnishings and was clean."
United States
Paul B.
The price is €341
includes taxes & fees
13 Apr - 14 Apr
Romantic Ocean Block Retreat – Steps to Beach, Ocean block Condo 100 steps from the beach

Amazing Views, Oceanfront Penthouse for families or large groups sleep 12 +

Amazing Views, Oceanfront Penthouse for families or large groups sleep 12 +
North Ocean City
9.0 out of 10, Wonderful, (71 reviews)
"Staff/security were very friendly and accommodating. Condo was very clean on arrival and despite it being the coldest weekend in the history of ocean city, the view was still wonderful."
United States
Jacqueline
The price is €552
includes taxes & fees
13 Apr - 14 Apr
Amazing Views, Oceanfront Penthouse for families or large groups sleep 12 +
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

Eastern Shore, a hidden gem on the Atlantic coast, offers a delightful mix of adventure and relaxation for families and discerning travellers alike. Start your journey in the charming town of St. Michaels, where you can explore the Chesapeake Bay Maritime Museum, a paradise of local history and maritime culture. After soaking in the sights, hop aboard a scenic cruise to witness the breathtaking views of the bay and its wildlife. For those who prefer land adventures, the Blackwater National Wildlife Refuge provides ample opportunities for birdwatching and hiking through lush trails. Don't miss the chance to visit the picturesque Oxford, known for its quaint shops and the Oxford-Bellevue Ferry, which offers a unique crossing experience. Finally, the vibrant town of Easton is perfect for shopping and dining, featuring farm-to-table restaurants that showcase the region's fresh seafood and local produce. When it comes to accommodation, staying in St. Michaels offers a delightful experience with charming inns and waterfront hotels that cater to families seeking comfort and quality service. Enjoy exploring the local boutiques by day and unwinding by the water in the evening, knowing that attentive staff are always ready to help you make the most of your stay. With a blend of natural beauty, charming towns, and quality experiences, Eastern Shore provides both adventure and relaxation, making it an ideal choice for family getaways.

Top Eastern Shore Hotel Reviews

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