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

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
    Sign in
  • Be picky

    Search almost a million properties worldwide

Check availability on Eastern Shore Romantic Hotels

Tonight
12 Oct - 13 Oct
Tomorrow
13 Oct - 14 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Our top choices for Eastern Shore romantic hotels

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

#1 Rated Condo, Oceanfront, with Bay View Too
North Ocean City
United States
Ed B.
€202
includes taxes & fees
26 Oct - 27 Oct
#1 Rated Condo, Oceanfront, with Bay View Too

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

Top-Rated Luxury Oceanfrt Condo Spectacular Views-Outstanding Reviews
North Ocean City
United States
Jay channel R.
€428
includes taxes & fees
1 Nov - 2 Nov
Top-Rated Luxury Oceanfrt Condo Spectacular Views-Outstanding Reviews

3. 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
United States
Mike G.
€269
includes taxes & fees
1 Nov - 2 Nov
BEACH PARADISE I - 4BR/3.5BA NEW GARAGE Townhouse with POOL in PRIME MIDTOWN OC!

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

Beach Paradise IV-Downtown Waterfront, Top Floor, Luxury Penthouse Condo
Downtown Ocean City
United States
Lisa K.
€306
includes taxes & fees
1 Nov - 2 Nov
Beach Paradise IV-Downtown Waterfront, Top Floor, Luxury Penthouse Condo

5. Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
United States
Harold B.
€238
includes taxes & fees
13 Oct - 14 Oct
Deal Island Bay Cottage

6. 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
United States
Cleotrina S.
€280
includes taxes & fees
20 Oct - 21 Oct
Beach Paradise III - DOWNTOWN OCEANVIEW Luxury Townhome-Steps to Beach&Boardwalk

7. Private 3 room Queen Suite w/Kitchenette

Private 3 room Queen Suite w/Kitchenette
Port Deposit
United States
Kathleen B.
€304
includes taxes & fees
13 Oct - 14 Oct
Private 3 room Queen Suite w/Kitchenette

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

DIRECT OCEANFRONT, Tiki Bar & Grill, Saunas, Gym,Tennis, WIFI & 3 Pools 5% off
North Ocean City
United States
Cromwell M.
€360
includes taxes & fees
25 Oct - 26 Oct
DIRECT OCEANFRONT, Tiki Bar & Grill, Saunas, Gym,Tennis, WIFI & 3 Pools 5% off

9. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Stevensville
United States
barbara s.
€1,227
includes taxes & fees
13 Oct - 14 Oct
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

10. 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
United States
Emma W.
BEACH PARADISE V - 4BR, 3.5BA NEW GARAGE Townhouse in PRIME MIDTOWN OC!
View all properties

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

Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

10/10 Excellent
"Several family members stayed here for a wedding in the area. Our suites were very nice. The full size refrigerator and even the stove came in very handy. The living area, bathroom and bedroom were roomy and comfortable. Would definitely stay here again."
Allison 3-night trip
Posted 4 hours ago
Princess Royale Oceanfront Resort
Quality Inn Oceanfront

Quality Inn Oceanfront

10/10 Excellent
"loved the courtyard with all the plants, the pool and hot tubs, the birds, the bar area. the bartenders were very friendly and informative"
yvonne 3-night trip
Posted 8 hours ago
Quality Inn Oceanfront
Days Inn by Wyndham Ocean City Oceanfront

Days Inn by Wyndham Ocean City Oceanfront

8/10 Good
"Great location and friendly staff"
Heather 2-night trip
Posted 8 hours ago
Days Inn by Wyndham Ocean City Oceanfront
St Michaels Inn

St Michaels Inn

10/10 Excellent
"na"
Jeffrey 2-night trip
Posted 9 hours ago
St Michaels Inn
Princess Bayside Beach Hotel

Princess Bayside Beach Hotel

8/10 Good
"Beautiful view"
Ellen 3-night trip
Posted 14 hours ago
Princess Bayside Beach Hotel
Ashore Oceanfront Hotel, Ocean City, a Tribute Portfolio Hotel

Ashore Oceanfront Hotel, Ocean City, a Tribute Portfolio Hotel

10/10 Excellent
"Was a pleasant stay would stay again or recommend to others"
Les 1-night trip
Posted 16 hours ago
Ashore Oceanfront Hotel, Ocean City, a Tribute Portfolio Hotel

Explore a world of travel with Expedia