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

Find 5 Star Hotels in Chesapeake Beach, MD from SAR 548

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Check availability on Chesapeake Beach 5 Star Hotels

Tonight
20 Oct - 21 Oct
Tomorrow
21 Oct - 22 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

Our top choices for Chesapeake Beach 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.
A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.
A golf course with a water hazard and surrounding trees.
A living room with a fireplace, a sofa, a coffee table, and a television mounted on the wall.

1. Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels
United States
Virgilio
SAR 1,842
SAR 2,026 total
includes taxes & fees
18 Nov - 19 Nov
Inn at Perry Cabin
A hot tub in a grassy area with a building in the background.
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.
A room with a tufted armchair, a vase with white flowers, and a window with a view of the outdoors.

2. The Inn at Tacaro Estate

The Inn at Tacaro Estate
Tracys Landing
United States
kristine
SAR 1,313
SAR 1,496 total
includes taxes & fees
17 Nov - 18 Nov
The Inn at Tacaro Estate
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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 Chesapeake Beach.
Rod 'N' Reel Resort

Rod 'N' Reel Resort

4165 Mears Ave Chesapeake Beach MD
SAR 494
SAR 548 total
9 Nov - 10 Nov
includes taxes & fees
8.6/10 Excellent! (1,008 reviews)
Rod 'N' Reel Resort
Legacy Villa

Legacy Villa

12605 Brooke Lane Upper Marlboro MD
Get ratesLegacy Villa
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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 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 fossilized 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?
There are a variety of pricing options for a 5-star hotel in Chesapeake Beach on Expedia. How much you'll pay will depend on when you plan to travel, trip length and other factors. Compare all of the available accommodations for your chosen dates and use our pricing and other filters to lock in the perfect high-end stay.
  • Search for the lowest price per night from SAR 548
What makes a hotel 5 stars in Chesapeake Beach?
In Chesapeake Beach, a hotel needs to provide a certain amount of top-notch amenities to earn 5 stars. These can include saunas and spas, on-site gyms, gourmet restaurants, luxury bathroom products, premium bedding and more. What also sets 5-star hotels apart is their outstanding standard of service. You can look forward to things like in-room massages, concierge services and nightly turn-down services. Some may even offer thoughtful touches like welcome gifts.
Are there any 5-star all-inclusive resorts in Chesapeake Beach?
Our filters are the quickest way to search for exactly what you want. Check the "All inclusive" and "5-star" boxes to show the most luxurious hotels in Chesapeake Beach where your lodging, meals, entertainment and activities are included in the price. At these stays, your trip is pure leisure from the moment you enter the lobby.