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

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Check availability on Eastern Shore Luxury Hotels

Tonight
22 Aug - 23 Aug
Tomorrow
23 Aug - 24 Aug
Next weekend
28 Aug - 30 Aug
In two weeks
4 Sept - 6 Sept

Our top choices for Eastern Shore luxury hotels

1. Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels
  • Waterfront luxury awaits with golf, spa, and marina at this St. Michaels coastal retreat.
S$595
includes taxes & fees
7 Sept - 8 Sept
Inn at Perry Cabin

2. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
  • Chesapeake Bay resort offers luxury with private beach, full-service spa, and championship golf.
S$365
includes taxes & fees
3 Sept - 4 Sept
Hyatt Regency Chesapeake Bay

3. Hilton Ocean City Oceanfront Suites

Hilton Ocean City Oceanfront Suites
Midtown Ocean City
S$321
includes taxes & fees
22 Sept - 23 Sept
Hilton Ocean City Oceanfront Suites

4. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
S$336
includes taxes & fees
31 Aug - 1 Sept
The Inn at Chesapeake Bay Beach Club

5. DoubleTree by Hilton Ocean City Oceanfront

DoubleTree by Hilton Ocean City Oceanfront
Midtown Ocean City
S$300
includes taxes & fees
21 Sept - 22 Sept
DoubleTree by Hilton Ocean City Oceanfront

6. Marvel's on the Creek

Marvel's on the Creek
East New Market
S$259
includes taxes & fees
2 Sept - 3 Sept
Marvel's on the Creek

7. The Oaks Waterfront

The Oaks Waterfront
Easton
S$615
includes taxes & fees
2 Sept - 3 Sept
The Oaks Waterfront

8. Cypress River Inn & Spa

Cypress River Inn & Spa
Snow Hill
S$287
includes taxes & fees
2 Sept - 3 Sept
Cypress River Inn & Spa

9. The Ivy Hotel

The Ivy Hotel
Midtown
  • Indulgent Baltimore retreat offering historic charm, a full-service spa, and fine dining.
S$1,026
includes taxes & fees
23 Aug - 24 Aug
The Ivy Hotel
View all properties

Find out more about Eastern Shore

Eastern Shoreand its attractions for luxury travelers

Eastern Shore, with its charming coastal towns and stunning landscapes, offers a wealth of experiences for discerning travellers seeking luxury. Begin your exploration in St. Michaels, where you can indulge in a private yacht charter on the tranquil Miles River, allowing you to soak in the picturesque views and perhaps spot some local wildlife. Next, head to the historic town of Easton, known for its vibrant arts scene; visit the Academy Art Museum and attend exclusive gallery openings while enjoying fine dining at one of the town's upscale restaurants. For a taste of nature, the Blackwater National Wildlife Refuge offers guided eco-tours, where you can witness the majestic bald eagles and serene marshlands in a luxury 4x4 vehicle. Don't miss the chance to unwind at one of the exquisite spas in Oxford, where bespoke treatments await you, tailored to rejuvenate and pamper. Finally, consider basing yourself in the opulent inns and boutique hotels found in these charming towns, where attentive service and elegant accommodation create a truly memorable stay. With easy access to all these experiences, the Eastern Shore promises both adventure and relaxation, making it a perfect getaway for the quality seeker.

Top Eastern Shore Hotel Reviews

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

10/10 Excellent
"Nice property the children really enjoyed the amenities."
Wayne 3-night trip
Posted 7 hours ago
Grand Hotel Ocean City Oceanfront
Howard Johnson by Wyndham Ocean City Oceanfront

Howard Johnson by Wyndham Ocean City Oceanfront

8/10 Good
"Room was clean and staff were super helpful and friendly. Room was a bit small and bathroom was no bigger than closet, but it was stocked well. Biggest complaint was that housekeeping skipped our room every single day even though we were out of the room by 10 am. Instead we would get a call or text from the hotel later in the day asking if we needed anything. I appreciated them checking with us, but it would have been nicer to just have the room ready. Pool was decent, beach towels available poolside. Parking lot was not big enough for number of spaces especially when people had bike carriers or trailer hitches. Overall stay was great."
Paul 4-night trip
Posted 9 hours ago
Howard Johnson by Wyndham Ocean City Oceanfront
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

10/10 Excellent
"Princess Royal is like a resort property rather than a standard hotel. The rooms are like a condominium equiped with a refridgerator, a range and standard kitchen appliances. Princess Royal is great for family vacation. Whenever we decide to visit Ocean City, MD, we will definitely seek Princess Royal as our vacation stay."
Ronald 4-night trip
Posted 10 hours ago
Princess Royale Oceanfront Resort
Ashore Oceanfront Hotel by Marriott

Ashore Oceanfront Hotel by Marriott

10/10 Excellent
"Staff was very professional and patient with my little girl ne."
Wandaa 2-night trip
Posted 10 hours ago
Ashore Oceanfront Hotel by Marriott
Castle in the Sand

Castle in the Sand

10/10 Excellent
"Loved the walk out suite right on the sand! It was so convenient to get to the beach, pool, and bar! Having a full kitchen was also really nice! We really love this hotel and can't wait to return!"
Amy 4-night trip
Posted 11 hours ago
Castle in the Sand
Princess Bayside Beach Hotel

Princess Bayside Beach Hotel

10/10 Excellent
"That was helpful. The room was very clean."
Tiffanie 2-night trip
Posted 11 hours ago
Princess Bayside Beach Hotel
Bonita Beach Hotel

Bonita Beach Hotel

10/10 Excellent
"Clean, convenient, no frills everything what we expected. I would stay again. Convenient to beach, restaurants and ample parking"
Timothy 2-night trip
Posted 15 hours ago
Bonita Beach Hotel

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