Aerial view of Chesapeake Beach marina with luxury sail boats, beach house apartments, fishing boats near the water park popular vacation spot for Washington residents in Calvery county Maryland

Find 5 Star Hotels in Chesapeake Beach, MD from ￥30,567

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Check availability on Chesapeake Beach 5 Star Hotels

Our top choices for Chesapeake Beach 5-star hotels

Breakfast, lunch, dinner and brunch served

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (390 reviews)
"maybe a little overpriced but a great place to stay in St Michaels!"
United States
Michel
The price is ￥106,926
￥117,619 total
includes taxes & fees
Jul 1 - Jul 2
Inn at Perry Cabin
Seasonal outdoor pool, pool umbrellas, sun loungers

The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.6 out of 10, Exceptional, (15 reviews)
"An amazing breakfast. The home is decorated beautifully"
United States
James
The price is ￥52,213
￥59,523 total
includes taxes & fees
Jun 14 - Jun 15
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
The price is ￥23,198 per night from Jun 23 to Jun 24
￥23,198
￥30,567 total
Jun 23 - Jun 24
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
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PoolSpaHot tubBreakfast includedWaterpark
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
Aerial view of Chesapeake Beach marina with luxury sail boats, beach house apartments, fishing boats near the water park popular vacation spot for Washington residents in Calvery county Maryland

Top Chesapeake Beach Hotel Reviews

Inn at Perry Cabin

Inn at Perry Cabin

10/10 Excellent
"It was a wonderful stay. The rooms were clean, the staff helpful and the food marvelous. I intend to visit again!"
Bill 2-night trip
Posted 3 days ago
Inn at Perry Cabin

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Chesapeake Beach?
The amount you pay for a 5-star hotel in Chesapeake Beach can vary according to when you decide to travel and how long you plan to stay, among a number of factors. Take advantage of our price per night filter and other search tools to score the best deal on a high-end stay.

  • Search for the lowest price per night from ￥30,567

What makes a hotel 5 stars in Chesapeake Beach?
From gourmet restaurants and all-day gyms to pools and superior bedding, the 5-star experience in Chesapeake Beach is all about relaxation and luxury. But it requires more than just top-notch perks to get a 5-star rating. Hotels must also deliver outstanding guest services like in-room massage treatments, dry cleaning and laundry and room service any time day or night.
Are there any 5-star all-inclusive resorts in Chesapeake Beach?
Find a luxury retreat that includes your lodging, meals, drinks and entertainment in Chesapeake Beach with our handy filters. Search for properties with a 5-star rating and select the "All inclusive" filter. Be sure to check what's included in the price. This way, you're ready to take advantage of all the premium perks from the moment you get there.