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

This weekend
Next weekend

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, (374 reviews)
"Fantastic - loved our stay!"
United States
Emily
The price is ¥65,499
¥72,050 total
includes taxes & fees
Apr 14 - Apr 15
Inn at Perry Cabin

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
4.0 star property
Cambridge
8.8 out of 10, Excellent, (1,001 reviews)
"Friendly and helpful staff, pleasant and comfortable room, good food, convenient location and wonderful scenery."
United States
Barry
The price is ¥32,388
¥44,363 total
includes taxes & fees
Mar 29 - Mar 30
Hyatt Regency Chesapeake Bay

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, (442 reviews)
"Very clean room, staff was very nice. "
United States
Byron
The price is ¥26,325
¥33,258 total
includes taxes & fees
Mar 30 - Mar 31
The Inn at Chesapeake Bay Beach Club

Hilton Ocean City Oceanfront Suites

Hilton Ocean City Oceanfront Suites
4.0 star property
Midtown Ocean City
8.8 out of 10, Excellent, (1,344 reviews)
"This is the hotel to stay to enjoy Ocean City MD"
United States
Young
The price is ¥25,502
¥28,564 total
includes taxes & fees
Apr 9 - Apr 10
Hilton Ocean City Oceanfront Suites

Marvel's on the Creek

Marvel's on the Creek
4.0 star property
East New Market
10.0 out of 10, Exceptional, (161 reviews)
"Exceptional bed and breakfast. Would definitely recommend to family and friends. "
United States
Delores
The price is ¥28,565
¥31,707 total
includes taxes & fees
Mar 27 - Mar 28
Marvel's on the Creek

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 view was gorgeous, restaurant on site was amazing "
United States
Ami
The price is ¥13,319
¥14,917 total
includes taxes & fees
Apr 19 - Apr 20
DoubleTree by Hilton Ocean City Oceanfront

The Oaks Waterfront

The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (41 reviews)
"Staff, breakfast, and room were all superb!"
United States
Jeffrey
The price is ¥69,839
¥76,823 total
includes taxes & fees
Mar 27 - Mar 28
The Oaks Waterfront

The Ivy Hotel

The Ivy Hotel
5.0 star property
Midtown
10.0 out of 10, Exceptional, (201 reviews)
"Yes room was spotless and staff very courteous "
United States
Teresa
The price is ¥102,640
¥120,601 total
includes taxes & fees
Mar 31 - Apr 1
The Ivy Hotel

Hotel Du Pont

Hotel Du Pont
4.5 star property
Downtown Wilmington
8.8 out of 10, Excellent, (656 reviews)
"The staff and room service food were excellent. The amenities (private car service, valet, room service) were excellent. The room itself was not what we expected for $800."
United States
James E
The price is ¥67,997
¥74,797 total
includes taxes & fees
Mar 27 - Mar 28
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, (32 reviews)
"A beautiful stay with amazing hosts!"
United States
Vineet
The price is ¥89,263
¥99,082 total
includes taxes & fees
Mar 28 - Mar 29
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