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

  • 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

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, (103 reviews)
"This property and its owner were everything we look for in a vacation rental. Listing is as an old farm house does not do it justice. The owner has carefully curated it it with an electric collection of furniture ,pottery and various hand crafted items. She has put her heart and soul into this house and you can feel.it ad soon as you step inside. We will definitely be back.😍😍😍😍😍 The McCartney's and the Horneffs.......Thanks again for everything Laurie."
United States
Melinda
The price is €264
includes taxes & fees
4 Jun - 5 Jun
BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen

Private 3 room Queen Suite w/Kitchenette

Private 3 room Queen Suite w/Kitchenette
Port Deposit
10.0 out of 10, Exceptional, (30 reviews)
"Perfect location for that town. "
United States
Hisham M.
Private 3 room Queen Suite w/Kitchenette

Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (59 reviews)
"We got every year and stay here, it’s great! "
United States
Margaret H.
The price is €237
includes taxes & fees
21 Jun - 22 Jun
Deal Island Bay Cottage

Relax, Unwind and Enjoy the Beach in a Fully Equipped Condo! Steps To The Ocean!

Relax, Unwind and Enjoy the Beach in a Fully Equipped Condo! Steps To The Ocean!
North Ocean City
9.6 out of 10, Exceptional, (141 reviews)
"Cute condo and great location !!!"
United States
Melissa M.
The price is €361
includes taxes & fees
17 Jun - 18 Jun
Relax, Unwind and Enjoy the Beach in a Fully Equipped Condo! Steps To The Ocean!

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 €291
includes taxes & fees
28 May - 29 May
Mid Town OceanSide/Block 46th St. Sleeps 5 Location, Location, Location!

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, (96 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.
Top-Rated Luxury Oceanfrt Condo Spectacular Views-Outstanding Reviews

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, (152 reviews)
"This is the second time my group of friends has stayed here. The house is very comfortable and well-appointed, and the view is gorgeous! "
United States
Melinda S.
The price is €477
includes taxes & fees
1 Jun - 2 Jun
5-bedroom vacation home 5 minutes from historic Charlestown

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 €343
includes taxes & fees
28 May - 29 May
Romantic Ocean Block Retreat – Steps to Beach, Ocean block Condo 100 steps from the beach

Its A Family Friendly House. Next To Convention Center. Minutes From The B.Walk

Its A Family Friendly House. Next To Convention Center. Minutes From The B.Walk
Midtown Ocean City
8.0 out of 10, Very good, (1 review)
"Open and spacious"
United States
william p.
Its A Family Friendly House. Next To Convention Center. Minutes From The B.Walk

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, (86 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
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

Explore a world of travel with Expedia