A marina with numerous sailboats docked at wooden piers.

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Check availability on Eastern Maryland 5 Star Hotels

This weekend
6 Nov - 8 Nov
Next weekend
13 Nov - 15 Nov

Our top choices for Eastern Maryland 5-star 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

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (407 reviews)
"Fantastic place; one of those that you don’t want to leave the property until the very sad time to go. Lovely staff, all of them, amazing food."
United States
Virgilio
The price is 12.606.178 ₫
13.866.796 ₫ total
includes taxes & fees
11 Nov - 12 Nov
Inn at Perry Cabin
A brick pathway leading to a pool area with a fence and potted plants.

2. Cypress River Inn & Spa

Cypress River Inn & Spa
5.0 star property
Snow Hill
8.6 out of 10, Excellent, (8 reviews)
"I fell in love with the charm of this Inn, I can't wait for the restaurant to be up and running so I can come back and stay."
United States
Hans
The price is 5.536.769 ₫
6.201.181 ₫ total
includes taxes & fees
5 Nov - 6 Nov
Cypress River Inn & Spa
Exterior

3. Inn at 202 Dover

Inn at 202 Dover
5.0 star property
Easton
10.0 out of 10, Exceptional, (14 reviews)
"Celebrated our 33rd anniversary here and enjoyed it thoroughly. Felt pampered and welcomed. Best B&B ever! Everything from the room to the food was exceptional. Every need was anticipated and met. Looking forward to our next visit. The quintessential "living like a king" experience."
United States
James
Inn at 202 Dover
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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Eastern Maryland.
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

100 Heron Blvd Cambridge MD
The price is 3.702.722 ₫ per night from 23 Nov to 24 Nov
3.702.722 ₫
4.938.753 ₫ total
23 Nov - 24 Nov
includes taxes & fees
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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.

Learn more about Eastern Maryland

Explore the walkable area of Eastern Maryland—beaches, boating and popular sights like Ocean City Beach.

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A building with a sign reading "Ward Museum of Wildfowl Art" and a large bird sculpture in front.

Top Eastern Maryland Hotel Reviews

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Eastern Maryland?
The amount you pay for a 5-star hotel in Eastern Maryland can vary according to when you prefer to travel and how long you plan to stay, among other factors. Use our price per night filter and other search tools to score the best rate on a high-end getaway.

  • Search for the lowest price per night from 2.342.321 ₫

What makes a hotel 5 stars in Eastern Maryland?
Impeccable guest service is the defining feature of every 5-star hotel in Eastern Maryland. From the minute you step through the door, staff attend to your every need, whether arranging customised tours or providing a turn-down service. In addition, hotels have to offer upscale amenities to qualify for a 5-star rating. These can include luxury toiletries, saunas or spas, pools, gastronomic kitchens and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Eastern Maryland?
Find a luxury escape that includes your room, meals, drinks and entertainment in Eastern Maryland with our filter tool. Search for properties with a 5-star rating and select the "All inclusive" filter. Have a look at what's included in the price. That way, you can take full advantage of all the premium perks as soon as you arrive.