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
Sep 6 - Sep 7
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Sep 7 - Sep 8
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Sep 11 - Sep 13
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Sep 18 - Sep 20

Our top choices for Eastern Shore luxury hotels

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

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.
NT$19,079
NT$20,987 total
includes taxes & fees
Sep 29 - Sep 30
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.
NT$7,309
NT$9,805 total
includes taxes & fees
Sep 29 - Sep 30
Hyatt Regency Chesapeake Bay
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.
A spacious dining area with round tables, high ceilings with ductwork, and a stone fireplace.
A spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.
A residential area with a garden, a patio with outdoor furniture, and a house with a chimney.

3. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
NT$6,051
NT$7,522 total
includes taxes & fees
Sep 8 - Sep 9
The Inn at Chesapeake Bay Beach Club
A resort pool area with lounge chairs, palm trees, and a boat-shaped water feature.
A dining table set with wine glasses, a bottle of Riesling wine, a vase with flowers, and a basket of bread.
An aerial view of a coastal city with a beachfront hotel featuring multiple floors, a swimming pool, and a marina in the background.
A large, multi-story hotel with a prominent Hilton sign, a parking lot with several cars, and a view of the ocean in the background.

4. Hilton Ocean City Oceanfront Suites

Hilton Ocean City Oceanfront Suites
Midtown Ocean City
NT$4,930
NT$5,521 total
includes taxes & fees
Oct 6 - Oct 7
Hilton Ocean City Oceanfront Suites
A balcony with wicker furniture and a table, overlooking a beach with umbrellas and people.
A swimming pool with lounge chairs and umbrellas, surrounded by large windows and a glass ceiling.
A living room with a beige sofa, blue and red patterned pillows, a wooden coffee table, and a view of the ocean through large windows.
A bar area with a long counter, multiple bar stools, and a pool table. There are tables and chairs for dining, and the room has large windows.

5. DoubleTree by Hilton Ocean City Oceanfront

DoubleTree by Hilton Ocean City Oceanfront
Midtown Ocean City
NT$3,347
NT$3,749 total
includes taxes & fees
Oct 5 - Oct 6
DoubleTree by Hilton Ocean City Oceanfront
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.

6. Marvel's on the Creek

Marvel's on the Creek
East New Market
NT$6,328
NT$7,024 total
includes taxes & fees
Sep 7 - Sep 8
Marvel's on the Creek
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools.
A white colonial-style house with a covered porch, brick steps, and outdoor seating.
A banquet hall with round tables set for dining, large windows with a view of a lake, and white chairs.
A deck with wicker furniture, a table, and an umbrella, overlooking a lake with trees and a dock.

7. The Oaks Waterfront

The Oaks Waterfront
Easton
NT$13,925
NT$15,317 total
includes taxes & fees
Sep 7 - Sep 8
The Oaks Waterfront
A brick pathway leading to a pool area with a fence and potted plants.
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 bedroom with a bed, a desk, a chair, a ceiling fan, and a patterned rug.
A two-story house with a balcony, a covered porch, and a brick chimney.

8. Cypress River Inn & Spa

Cypress River Inn & Spa
Snow Hill
NT$6,800
NT$7,616 total
includes taxes & fees
Sep 7 - Sep 8
Cypress River Inn & Spa
A hot tub in a grassy area with a building in the background.
A luxurious living room with a leather sofa, a vintage trunk, and a fireplace.
A pool with two Adirondack chairs and a basket of items on the grass.
A room with a tufted armchair, a vase with white flowers, and a window with a view of the outdoors.

9. 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.
NT$12,549
NT$14,306 total
includes taxes & fees
Sep 13 - Sep 14
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 marina with boats docked, a bridge, and buildings with illuminated windows.
A spa room with cushioned seating, a glass door leading outside, and a ceiling light fixture.

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.
NT$14,950
NT$17,566 total
includes taxes & fees
Sep 23 - Sep 24
Four Seasons Hotel Baltimore
View all properties

Top Eastern Shore Hotel Reviews

Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

10/10 Excellent
"The place was great. Every room is like a 1 bedroom apartment with a full kitchen. The price was great for what you are getting."
Thomas 4-night trip
Posted 4 hours ago
Princess Royale Oceanfront Resort
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

10/10 Excellent
"Clean friendly and pool restaurant every thing right there"
jean 1-night trip
Posted 4 hours ago
Grand Hotel Ocean City Oceanfront
Castle in the Sand

Castle in the Sand

10/10 Excellent
"Great place to stay staff friendly very helpful two restaurants on site ocean view cannot be beat and cheaper than a lot of other options in the area. I highly highly recommend"
Reginald 2-night trip
Posted 7 hours ago
Castle in the Sand
Crystal Beach Hotel

Crystal Beach Hotel

10/10 Excellent
"The check-in was smooth and quick the room was nice its right on the boardwalk and close to many places to eat. I enjoyed it."
Eric 1-night trip
Posted 13 hours ago
Crystal Beach Hotel
Princess Bayside Beach Hotel

Princess Bayside Beach Hotel

8/10 Good
"We stayed in a bayfront balcony room, and the view was absolutely amazing. The small private beach on the bay was a wonderful bonus and a great place to relax. We also really enjoyed the rooftop pool, which offered stunning bay views as well. The room itself was comfortable, although a bit dated. That said, it certainly wasn't anything that would keep us from returning. If you're looking for a very quiet retreat, however, this may not be the best fit. We found the air conditioning unit to be quite loud, and noise traveled easily throughout the building. Room doors tended to slam, the elevator's chime could be heard frequently, and hallway conversations and footsteps were surprisingly noticeable from inside the room. While those are important things to mention, they didn't detract significantly from our overall experience. The incredible view, convenient bay access, and private beach more than made up for the noise. We thoroughly enjoyed our stay and would definitely come back."
Sherri 5-night trip
Posted 14 hours ago
Princess Bayside Beach Hotel
Fenwick Inn

Fenwick Inn

10/10 Excellent
"Great"
Yunshen 7-night trip
Posted 22 hours ago
Fenwick Inn

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