A harbor with boats docked, a pier, and a row of houses along the water.

Compare and book 5 Star hotels in Chesapeake Beach, Maryland

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Check availability on Chesapeake Beach 5 Star Hotels

This weekend
31 Jul - 2 Aug
Next weekend
7 Aug - 9 Aug

Our top choices for Chesapeake Beach 5-star hotels

Premium bedding, down duvets, in-room safe, desk

1. Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (395 reviews)
"maybe a little overpriced but a great place to stay in St Michaels!"
United States
Michel
The price is 16.346.583 ₫
17.981.242 ₫ total
includes taxes & fees
26 Aug - 27 Aug
Inn at Perry Cabin
Seasonal outdoor pool, pool umbrellas, pool loungers

2. The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.6 out of 10, Exceptional, (18 reviews)
"An amazing breakfast. The home is decorated beautifully"
United States
James
The price is 8.963.245 ₫
10.218.062 ₫ total
includes taxes & fees
6 Aug - 7 Aug
The Inn at Tacaro Estate
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Learn more about Chesapeake Beach

Stroll the half-mile boardwalk at sunset, where fishing boats return with the day's catch and locals gather for crab feasts. Families splash in the water park's eight slides by day, then hunt for fossilised shark teeth along the Bay's ancient shoreline.

See all hotels in Chesapeake Beach
A coastal town with a marina, residential buildings, and a clear sky.

Top Chesapeake Beach Hotel Reviews

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Chesapeake Beach?
How much you pay for a 5-star hotel in Chesapeake Beach depends on things like when you plan to travel and the length of your escape. A top tip for scoring an awesome deal? Use our pricing filters to compare all of the available options for your preferred dates.

  • Search for the lowest price per night

What makes a hotel 5 stars in Chesapeake Beach?
Flawless guest service is integral to every 5-star hotel in Chesapeake Beach. From the moment you enter the lobby, staff are at your beck and call, whether arranging customised tours or providing in-room massage treatments. In addition, hotels have to feature upscale conveniences to obtain a 5-star rating. These can include luxury toiletries, an on-site spa, swimming pools, fine dining restaurants and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Chesapeake Beach?
Expedia's filter tool is the quickest way to search for exactly what you're looking for. Select "5-star" and "All inclusive" to see the most luxurious hotels in Chesapeake Beach where your meals, room, entertainment and activities are included in the price. At these stays, your holiday is pure indulgence from the moment you enter the lobby.