The Best Romantic Hotels in Eastern Shore, MD from ￥40,575 in 2026

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check availability on Eastern Shore Romantic Hotels

Tonight

Tomorrow

Next weekend

In two weeks

Our top choices for Eastern Shore romantic hotels

A balcony with two chairs and a table, overlooking a beach with the ocean and a clear sky.

A multi-story hotel with balconies, located near a beach with umbrellas.

A living room with a television, a dining table, chairs, a sofa, a coffee table, and a potted plant.

A rooftop pool with a view of the beach and ocean.

1. #1 Rated Condo, Oceanfront, with Bay View Too

North Ocean City

Ed B.

￥14,049

￥44,022 total

includes taxes & fees

Oct 4 - Oct 5

A waterfront property with multiple-story buildings, a dock with boats, and a wooden pier.

A modern kitchen with white cabinets, stainless steel appliances, and a wooden dining area with a bench.

A waterfront hotel with a dock, a calm river, and a clear blue sky.

A modern kitchen with white cabinets, a central island, and a dining area with a wooden table and wicker chairs.

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

North Ocean City

Mike G.

￥7,103

￥46,496 total

includes taxes & fees

Nov 1 - Nov 2

A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a large island with stools.

Two people fishing on a sandy beach with a sunset in the background.

A covered outdoor area with a table and chairs, a grill, and a view of the surrounding landscape.

A bedroom with a bed, a desk, a chair, a wardrobe, a ceiling fan, and a window.

3. Deal Island Bay Cottage

Deal Island

"We loved this place! We were in town for baseball. It is very nice and has all the comforts of home. Kitchen big and well equipped, house was clean and very well furnished. Nice bathrooms and a lovely screened in back porch. It is very near a beautiful beach on the bay that has some of the most beautiful sunsets you will ever see. We really enjoyed this perk!! Prompt communication and everything was as described. I highly recommend this rental!!"

Harold B.

￥22,020

￥40,575 total

includes taxes & fees

Oct 6 - Oct 7

A living room with a sofa, a lamp, a TV, and a view of the sea through a balcony.

A hallway with white paneled walls, a tiled floor, and a door leading outside.

A modern kitchen with stainless steel appliances, a dining area with a view, and a teal console table with decorative items.

A spacious living room with a sofa, armchairs, and a coffee table. A kitchen is visible in the background.

4. Beach Paradise IV-Downtown Waterfront, Top Floor, Luxury Penthouse Condo

Downtown Ocean City

Lisa K.

￥7,103

￥53,568 total

includes taxes & fees

Nov 1 - Nov 2

A dining area with a wooden table set for four, surrounded by wicker chairs.

A row of white multi-story residential buildings with balconies, a clear sky, and a straight street in the foreground.

A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and a dining area with wicker chairs and a bench.

A dining area with a wooden table set for two, a wicker chair, and a grey sofa with cushions.

5. "BEACH PARADISE II" 4-BR/3.5-BA Exquisite Townhouse with POOL & GARAGE

North Ocean City

Rebecca D.

￥12,010

￥54,160 total

includes taxes & fees

Oct 4 - Oct 5

A balcony with wicker furniture overlooking the ocean.

A modern living room with a striped sofa, wooden chairs, a glass coffee table, and a view of the ocean through large windows.

An indoor swimming pool with clear glass ceilings, lounge chairs, and a view of the outside.

A beach with a sandy shore, a clear blue sky, and a calm sea.

6. Top-Rated Luxury Oceanfrt Condo Spectacular Views-Outstanding Reviews

North Ocean City

Jay channel R.

￥15,627

￥72,131 total

includes taxes & fees

Nov 1 - Nov 2

A modern living room with a sofa, coffee table, dining table, and chairs. There is a TV mounted on the wall and artwork displayed above the table.

A modern kitchen with white cabinetry, a central island, and a dining area with white chairs and a wooden table.

A modern living room with a blue sofa, a wooden coffee table, and a striped rug.

A modern kitchen with wooden cabinets, a central island with stools, and a view of the living area.

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

Downtown Ocean City

Cleotrina S.

￥9,234

￥50,120 total

includes taxes & fees

Oct 20 - Oct 21

A wooden gazebo with a table and chairs, surrounded by plants and a grill.

A staircase with white and dark wooden steps leading to a second floor. A wooden handrail is on the left, and a white vase is on the right.

A cozy room with wicker furniture, a blue vase, and a view of the outdoors through large windows.

A modern kitchen with white cabinets, stainless steel appliances, a central island, and a blue stool.

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

Berlin

Jim C.

￥31,570

￥60,640 total

includes taxes & fees

Oct 4 - Oct 5

View all properties

Top Eastern Shore Hotel Reviews

Crystal Beach Hotel

10/10 Excellent

"The hotel was wonderful. It was clean and the staff was friendly and helpful. The lobby is in one building on the second floor and we were in the boardwalk building. The balconies had no petitions"

Days Inn by Wyndham Ocean City Oceanfront

8/10 Good

"room was clean and comfortable. The only concern was no hot water or soap in the shower dispenser"

Explore a world of travel with Expedia

Rental cars Cambridge - Dorchester airport

Book Romantic Hotels in Eastern Shore on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Eastern Shore Romantic Hotels

Our top choices for Eastern Shore romantic hotels

1. #1 Rated Condo, Oceanfront, with Bay View Too

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

3. Deal Island Bay Cottage

4. Beach Paradise IV-Downtown Waterfront, Top Floor, Luxury Penthouse Condo

5. "BEACH PARADISE II" 4-BR/3.5-BA Exquisite Townhouse with POOL & GARAGE

6. Top-Rated Luxury Oceanfrt Condo Spectacular Views-Outstanding Reviews

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

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

9. Private 3 room Queen Suite w/Kitchenette

10. DIRECT OCEANFRONT, Tiki Bar & Grill, Saunas, Gym,Tennis, WIFI & 3 Pools 5% off

Top Eastern Shore Hotel Reviews

Crystal Beach Hotel

Days Inn by Wyndham Ocean City Oceanfront

Explore a world of travel with Expedia

Find Romantic Hotels in Eastern Shore, MD

Change your mind

Treat yourself

Be picky

Check availability on Eastern Shore Romantic Hotels

Our top choices for Eastern Shore romantic hotels

1. #1 Rated Condo, Oceanfront, with Bay View Too

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

3. Deal Island Bay Cottage

4. Beach Paradise IV-Downtown Waterfront, Top Floor, Luxury Penthouse Condo

5. "BEACH PARADISE II" 4-BR/3.5-BA Exquisite Townhouse with POOL & GARAGE

6. Top-Rated Luxury Oceanfrt Condo Spectacular Views-Outstanding Reviews

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

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

9. Private 3 room Queen Suite w/Kitchenette

10. DIRECT OCEANFRONT, Tiki Bar & Grill, Saunas, Gym,Tennis, WIFI & 3 Pools 5% off

Top Eastern Shore Hotel Reviews

Crystal Beach Hotel

Days Inn by Wyndham Ocean City Oceanfront

Explore a world of travel with Expedia