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
Oct 5 - Oct 6
Tomorrow
Oct 6 - Oct 7
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Eastern Shore luxury hotels

A room with a view of a wooden deck and a gazebo by the water.
A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.
A golf course with a water hazard and surrounding trees.
A hotel room with a large bed, a chair, a desk, and a television.

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.
₩687,595
₩756,354 total
includes taxes & fees
Oct 26 - Oct 27
Inn at Perry Cabin
An indoor swimming pool with lounge chairs and tables, large windows, and a high wooden ceiling.
A spacious dining area with multiple tables and chairs, high ceilings with exposed beams, and a brick wall.
A marina with boats docked, a large building with a tower in the background, and a dock extending into the water.
A spacious dining area with high ceilings, large windows, and modern chandeliers.

2. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
  • Chesapeake Bay resort offers luxury with private beach, full-service spa, and championship golf.
₩256,005
₩354,499 total
includes taxes & fees
Nov 4 - Nov 5
Hyatt Regency Chesapeake Bay
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.
A bar area with multiple seating options, a variety of bottles and glasses on shelves, and a modern chandelier.
A residential area with a garden, a patio with outdoor furniture, and a house with a chimney.
A spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

3. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
₩256,340
₩318,639 total
includes taxes & fees
Oct 19 - Oct 20
The Inn at Chesapeake Bay Beach Club
A wooden dock with a bench and a wooden post with a light fixture.
A wooden dock leading to a house with a lawn and a pond.
A corner room with a window overlooking a green field, a wooden barrel, a chair, and a small table with a candle and flowers.
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

Marvel's on the Creek
East New Market
₩268,068
₩297,556 total
includes taxes & fees
Oct 6 - Oct 7
Marvel's on the Creek
A modern living room with a large window overlooking the sea, a sofa, a fireplace, and a flat-screen TV mounted on the wall.
A modern bathroom with a large bathtub, a white sink, and a view of the sea through large windows.
A modern living room with a large sofa, a coffee table, and a TV. There are large windows with a view of the water and a balcony.
A bedroom with a bed, a sofa, a TV, a fireplace, and a view of the sea.

5. The Edge at Fager's Island

The Edge at Fager's Island
Midtown Ocean City
  • Seaside luxury awaits at this adults-only hotel, offering spectacular bay sunset views and indulgent jetted tubs in each intimate room.
₩365,913
₩409,823 total
includes taxes & fees
Nov 1 - Nov 2
The Edge at Fager's Island
A brick pathway leading to a pool area with a fence and potted plants.
A bedroom with a bed, a desk, a chair, a ceiling fan, and a patterned rug.
A living room with a flat-screen TV on a wooden cabinet, a coffee machine on a shelf, and a door leading to another room.
A dining room with a large wooden table, matching chairs, a chandelier, and a patterned rug.

6. Cypress River Inn & Spa

Cypress River Inn & Spa
Snow Hill
₩288,066
₩322,634 total
includes taxes & fees
Oct 6 - Oct 7
Cypress River Inn & Spa
A waterfront property with a prominent building featuring a red roof and a tower, surrounded by water and marshland.
A rocking chair on a wooden deck with a view of the ocean and a sunset.
A spacious lobby with wooden ceiling, comfortable seating, large windows, and a fireplace.
A cozy living room with a fireplace, a chessboard, and a tray with snacks and drinks.

7. Lighthouse Club Hotel

Lighthouse Club Hotel
Midtown Ocean City
  • Luxury coastal retreat with frette italian sheets, nightclub, and spa services near ocean city beach.
₩261,366
₩292,730 total
includes taxes & fees
Oct 12 - Oct 13
Lighthouse Club Hotel
A hot tub in a grassy area with a building in the background.
A cozy room with a brick fireplace, leather armchairs, and a rustic wooden table.
A pool with two Adirondack chairs and a basket of items on the grass.
A luxurious living room with a leather sofa, a vintage trunk, and a fireplace.

8. The Inn at Tacaro Estate

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.
₩468,891
₩534,541 total
includes taxes & fees
Nov 1 - Nov 2
The Inn at Tacaro Estate
A modern building with a bar area, outdoor seating, and a pool.
A modern dining area with a large table, chairs, and a view of a cityscape through large windows.
A hotel lobby with a reflective floor, a reception desk, and a large floral arrangement.
A spa room with cushioned seating, a glass door leading outside, and a ceiling light fixture.

9. 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.
₩569,645
₩669,334 total
includes taxes & fees
Nov 3 - Nov 4
Four Seasons Hotel Baltimore
A historic building with a prominent facade, large arched windows, and a central entrance.
A restaurant interior with brick walls, wooden tables, and hanging pendant lights.
A waterfront hotel with a pool, outdoor seating, and a view of the cityscape.
A modern lounge area with round tables, cushioned chairs, and a large floral painting on the wall.

10. Pendry Baltimore

Pendry Baltimore
Fells Point
  • Immerse in harbor-side luxury at Baltimore's Pendry hotel, where elegant relaxation meets waterfront sophistication.
₩485,203
₩625,241 total
includes taxes & fees
Nov 3 - Nov 4
Pendry Baltimore
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Top Eastern Shore Hotel Reviews

Princess Bayside Beach Hotel

Princess Bayside Beach Hotel

8/10 Good
"Nice place. Great location"
Adrienne 2-night trip
Posted 6 hours ago
Princess Bayside Beach Hotel
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

8/10 Good
"The room was spacious and clean but for the price, the amenities were just okay. The pool is weirdly situated inside a gate next to an arcade that I'm guessing no one uses. Not a lot of space to sit near the poolside bar."
Tiffany 2-night trip
Posted 9 hours ago
Princess Royale Oceanfront Resort
Plim Plaza Hotel

Plim Plaza Hotel

8/10 Good
"Great stay, love that they have entertainment and everything you need right there and it was just steps from the country calling music festival."
Nina 3-night trip
Posted 10 hours ago
Plim Plaza Hotel
Tidelands Caribbean Hotel and Suites

Tidelands Caribbean Hotel and Suites

10/10 Excellent
"Room was clean and staff was great."
Dawn 3-night trip
Posted 15 hours ago
Tidelands Caribbean Hotel and Suites
Castle in the Sand

Castle in the Sand

8/10 Good
"The rooms were clean but lacked stuff to do dishes with and coffee"
Jessica 3-night trip
Posted 16 hours ago
Castle in the Sand
Carousel Resort Hotel & Condominiums

Carousel Resort Hotel & Condominiums

8/10 Good
"Rooms are decent. Beds are so uncomfortable though, we could barely sleep. My AC didn’t work either. Pool and hot tub area could use a good cleaning and upgrades. Hot tub doesn’t get up to appropriate temperature. Staff were very helpful though.coffee at the Bistro was excellent as well!"
Katie 3-night trip
Posted 16 hours ago
Carousel Resort Hotel & Condominiums
The Shore House

The Shore House

8/10 Good
"Quick one night stay before checking into our boardwalk hotel for the week. Clean small room with everything needed for one night. Easy check in and friendly staff. Would recommend for sure!"
Bree 1-night trip
Posted 19 hours ago
The Shore House
Quality Inn Oceanfront

Quality Inn Oceanfront

8/10 Good
"The room was clean and comfortable. The staff was friendly and helpful. The view was excellent. The property is somewhat dated and could use updated."
Carol 1-night trip
Posted 1 day ago
Quality Inn Oceanfront
St Michaels Inn

St Michaels Inn

10/10 Excellent
"Late night manager was extremely helpful!"
Rodney 1-night trip
Posted 4 days ago
St Michaels Inn

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