Find Luxury Hotels in Eastern Shore, MD

  • 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 Luxury Hotels

Next weekend
In two weeks

Our top choices for Eastern Shore luxury hotels

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (387 reviews)
  • cleanliness
    Waterfront luxury awaits with golf, spa, and marina at this St. Michaels coastal retreat.
The price is ¥112,523
¥123,776 total
includes taxes & fees
Jun 24 - Jun 25
Inn at Perry Cabin

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
4.0 star property
Cambridge
8.8 out of 10, Excellent, (1,003 reviews)
  • cleanliness
    Chesapeake Bay resort offers luxury with private beach, full-service spa, and championship golf.
The price is ¥40,707
¥53,835 total
includes taxes & fees
Jun 9 - Jun 10
Hyatt Regency Chesapeake Bay

Hilton Ocean City Oceanfront Suites

Hilton Ocean City Oceanfront Suites
4.0 star property
Midtown Ocean City
8.8 out of 10, Excellent, (1,349 reviews)
The price is ¥52,493
¥58,791 total
includes taxes & fees
Jun 8 - Jun 9
Hilton Ocean City Oceanfront Suites

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (456 reviews)
The price is ¥36,100
¥44,142 total
includes taxes & fees
Jun 15 - Jun 16
The Inn at Chesapeake Bay Beach Club

DoubleTree by Hilton Ocean City Oceanfront

DoubleTree by Hilton Ocean City Oceanfront
4.0 star property
Midtown Ocean City
9.0 out of 10, Wonderful, (1,002 reviews)
The price is ¥35,042
¥39,248 total
includes taxes & fees
Jun 8 - Jun 9
DoubleTree by Hilton Ocean City Oceanfront

Marvel's on the Creek

Marvel's on the Creek
4.0 star property
East New Market
10.0 out of 10, Exceptional, (166 reviews)
The price is ¥28,802
¥31,970 total
includes taxes & fees
Jun 17 - Jun 18
Marvel's on the Creek

The Oaks Waterfront

The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (41 reviews)
The price is ¥70,420
¥77,462 total
includes taxes & fees
Jun 14 - Jun 15
The Oaks Waterfront

The Ivy Hotel

The Ivy Hotel
5.0 star property
Midtown
10.0 out of 10, Exceptional, (207 reviews)
  • cleanliness
    Indulgent Baltimore retreat offering historic charm, a full-service spa, and fine dining.
The price is ¥109,908
¥129,144 total
includes taxes & fees
Jun 17 - Jun 18
The Ivy Hotel

Hotel Du Pont

Hotel Du Pont
4.5 star property
Downtown Wilmington
8.8 out of 10, Excellent, (658 reviews)
  • cleanliness
    Timeless elegance meets modern luxury in historic Wilmington, with on-site spa and refined dining options.
The price is ¥87,037
¥95,741 total
includes taxes & fees
Jul 1 - Jul 2
Hotel Du Pont

Swanendele Inn at St. Mary's Maryland

Swanendele Inn at St. Mary's Maryland
5.0 star property
Ridge
9.8 out of 10, Exceptional, (33 reviews)
  • cleanliness
    Seaside luxury unfolds at this Maryland inn with a private beach, kayaking, and champagne service.
The price is ¥51,351
¥56,999 total
includes taxes & fees
Jun 8 - Jun 9
Swanendele Inn at St. Mary's Maryland
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 Shoreand its attractions for luxury travelers

Luxury travelers seeking an exquisite getaway on the Eastern Shore will find a paradise of experiences that cater to their refined tastes. Start your journey in Easton, where you can explore the historic Avalon Theatre, known for its stunning architecture and vibrant performing arts scene. After taking in a show, indulge in a wine tasting at the nearby Eastern Shore Wine Trail, which boasts charming wineries that feature tastings paired with gourmet bites. For nature lovers, the serene landscapes of the Blackwater National Wildlife Refuge offer opportunities for guided birdwatching tours, where you can spot majestic eagles and migratory birds in their natural habitat. Head to St. Michaels, a picturesque waterfront town, to enjoy upscale dining at The Crab Claw, famous for its fresh seafood and waterfront views. Finally, unwind at the luxurious resorts along the Chesapeake Bay, such as the Inn at Perry Cabin, where you can enjoy personalized spa treatments, fine dining, and stunning views of the water. The combination of rich culture, natural beauty, and luxurious accommodations makes the Eastern Shore a delightful escape for those who appreciate the finer things in life.

Top Eastern Shore Hotel Reviews

Explore a world of travel with Expedia