The Best Luxury Hotels in Eastern Shore, MD from ￥26,847 in 2026

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Our top choices for Eastern Shore luxury hotels

A room with a fireplace, a dining area with chairs, a large window with a view of the outside, and a cabinet with bottles.

1. Inn at Perry Cabin

Downtown St. Michaels

Waterfront luxury awaits with golf, spa, and marina at this St. Michaels coastal retreat.

￥80,668 total

includes taxes & fees

Dec 7 - Dec 8

A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

2. The Inn at Chesapeake Bay Beach Club

Stevensville

￥36,169 total

includes taxes & fees

Dec 9 - Dec 10

A resort with a large pool, outdoor seating, and a view of the sea.

3. Hyatt Regency Chesapeake Bay

Cambridge

Chesapeake Bay resort offers luxury with private beach, full-service spa, and championship golf.

￥35,004 total

includes taxes & fees

Nov 15 - Nov 16

A sunlit room with a checkered sofa, wicker chairs, a glass table, and large windows offering a view of greenery.

4. Marvel's on the Creek

East New Market

￥34,050 total

includes taxes & fees

Dec 13 - Dec 14

A brick pathway leading to a pool area with a fence and potted plants.

5. Cypress River Inn & Spa

Snow Hill

￥33,237 total

includes taxes & fees

Nov 24 - Nov 25

A high-rise building with a glass facade, a waterfront view, and a small park with white tents.

6. 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.

￥79,786 total

includes taxes & fees

Dec 13 - Dec 14

A modern living room with a fireplace, two sofas, a coffee table with a book, and a view of the sea.

7. Pendry Baltimore

Fells Point

Immerse in harbor-side luxury at Baltimore's Pendry hotel, where elegant relaxation meets waterfront sophistication.

￥77,212 total

includes taxes & fees

Dec 13 - Dec 14

A grand, marble staircase with ornate iron railings and a central handrail, leading to a door with a chandelier above.

8. Hotel Du Pont

Downtown Wilmington

Timeless elegance meets modern luxury in historic Wilmington, with on-site spa and refined dining options.

￥79,243 total

includes taxes & fees

Nov 23 - Nov 24

A modern brick building with large windows, a balcony, and a staircase.

9. The Ivy Hotel

Midtown

Indulgent Baltimore retreat offering historic charm, a full-service spa, and fine dining.

￥133,437 total

includes taxes & fees

Nov 15 - Nov 16

A hot tub in a grassy area with a building in the background.

10. The Inn at Tacaro Estate

Tracys Landing

Indulge in beachside luxury at this 5-star estate featuring a seasonal outdoor pool, private balconies, and Italian Frette sheets.

￥54,161 total

includes taxes & fees

Nov 23 - Nov 24

View all properties

Top Eastern Shore Hotel Reviews

Inn at Perry Cabin

Downtown St. Michaels

10/10 Excellent

Norm

Four Seasons Hotel Baltimore

Harbor East

10/10 Excellent

Our stay at the Four Seasons was excellent from valet parking, front desk, housekeeper to room service. The customer service was unbelievable. I would like to thank the Four Seasons for this because I was praying that they wouldn't treat us bad because of the color of our skin. This mean so much to me because my husband had a wonderful dinner at the Bygone. Thank for making my husband Birthday so awesome and special. Now the gentleman that found my bag and turned it in. He was apart of valet...

Katrina

The Ivy Hotel

Midtown

10/10 Excellent

My stay at The Hotel Ivy was an experience I will never forget. This charming upscale hotel makes you feel welcome from the moment you step out of your car. This is 5 star elegance in a warm and comfortable atmosphere. The restaurant, high tea, rooms, and complimentary services are first rate. The staff at The Ivy Hotel are exceptional. They take the time to know your name, your preferences, and make you feel at home. My best friend and I equally enjoyed getting to know the people who...

Regina

The Inn at Tacaro Estate

Tracys Landing

10/10 Excellent

ian

A wooden double door with glass panels, a porch with a railing, and a view of the outdoors.

Swanendele Inn at St. Mary's Maryland

Ridge

10/10 Excellent

dina

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.

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Find Luxury Hotels in Eastern Shore, MD

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Eastern Shore luxury hotels

1. Inn at Perry Cabin

2. The Inn at Chesapeake Bay Beach Club

3. Hyatt Regency Chesapeake Bay

4. Marvel's on the Creek

5. Cypress River Inn & Spa

6. Four Seasons Hotel Baltimore

7. Pendry Baltimore

8. Hotel Du Pont

9. The Ivy Hotel

10. The Inn at Tacaro Estate

Top Eastern Shore Hotel Reviews

Inn at Perry Cabin

10/10 Excellent

Find out more about Eastern Shore

Eastern Shoreand its attractions for luxury travelers

Explore a world of travel with Expedia