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

Find Luxury Hotels in Eastern Shore, MD

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Check availability on Eastern Shore Luxury Hotels

Tonight
Sep 29 - Sep 30
Tomorrow
Sep 30 - Oct 1
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

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.
₩696,937
₩766,630 total
includes taxes & fees
Oct 26 - Oct 27
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.
₩281,647
₩384,258 total
includes taxes & fees
Oct 26 - Oct 27
Hyatt Regency Chesapeake Bay

3. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
₩259,823
₩322,965 total
includes taxes & fees
Oct 19 - Oct 20
The Inn at Chesapeake Bay Beach Club

4. Marvel's on the Creek

Marvel's on the Creek
East New Market
₩270,814
₩300,603 total
includes taxes & fees
Sep 30 - Oct 1
Marvel's on the Creek

5. Hilton Ocean City Oceanfront Suites

Hilton Ocean City Oceanfront Suites
Midtown Ocean City
₩183,206
₩205,190 total
includes taxes & fees
Oct 27 - Oct 28
Hilton Ocean City Oceanfront Suites

6. DoubleTree by Hilton Ocean City Oceanfront

DoubleTree by Hilton Ocean City Oceanfront
Midtown Ocean City
₩132,095
₩147,945 total
includes taxes & fees
Oct 12 - Oct 13
DoubleTree by Hilton Ocean City Oceanfront

7. The Oaks Waterfront

The Oaks Waterfront
Easton
₩595,926
₩655,519 total
includes taxes & fees
Oct 1 - Oct 2
The Oaks Waterfront

8. Cypress River Inn & Spa

Cypress River Inn & Spa
Snow Hill
₩291,017
₩325,939 total
includes taxes & fees
Sep 30 - Oct 1
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.
₩968,837
₩1,138,383 total
includes taxes & fees
Oct 8 - Oct 9
The Ivy Hotel

10. Four Seasons Hotel Baltimore

Four Seasons Hotel Baltimore
Harbor East
  • Indulgent waterfront retreat with 5 restaurants and a full-service spa offers a lavish Baltimore experience in Harbor East.
₩639,798
₩751,763 total
includes taxes & fees
Oct 11 - Oct 12
Four Seasons Hotel Baltimore
View all properties

Top Eastern Shore Hotel Reviews

Castle in the Sand

Castle in the Sand

10/10 Excellent
"Nice front desk guy. Typical OC room but clean"
Mike 2-night trip
Posted 5 hours ago
Castle in the Sand
Plim Plaza Hotel

Plim Plaza Hotel

10/10 Excellent
"We had an absolute blast staying here. The staff and the other guests were great! We were there for the Nor’Easter and although the Oceans Calling Festival was cancelled and the weather was awful we still had fun. We did cut our stay short due to deteriorating weather conditions, but booked for next year before we left. If you want a clean place to stay and want to be surrounded by all the OC Boardwalk has to offer, look no further. Yes, the rooms are small but what are you doing in your room? Go outside, hang out on the porch or the huge lobby. So much fun."
Lori 4-night trip
Posted 14 hours ago
Plim Plaza Hotel
Quality Inn Oceanfront

Quality Inn Oceanfront

8/10 Good
"bathroom tub and fixtures needs to be upgraded. Staff is both courtesy and helpful."
Robin 2-night trip
Posted 1 day ago
Quality Inn Oceanfront

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