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

5 Stars Hotels in Chesapeake Beach, Maryland from CA $315

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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, (393 reviews)
"maybe a little overpriced but a great place to stay in St Michaels!"
United States
Michel
The price is CA $912
CA $1,003 total
includes taxes & fees
Aug 19 - Aug 20
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, (17 reviews)
"An amazing breakfast. The home is decorated beautifully"
United States
James
The price is CA $477
CA $544 total
includes taxes & fees
Jul 28 - Jul 29
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 CA $241 per night from Aug 4 to Aug 5
CA $241
CA $315 total
Aug 4 - Aug 5
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
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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

Inn at Perry Cabin

Inn at Perry Cabin

10/10 Excellent
"Beautiful property, very well maintained. Dinner and Brunch at Stars were both very good. We loved being by the boats. Staff was accommodating when I had to do a zoom call on the morning of departure and found me a quiet private spot. Short walk to the Maritime Museum which was worth going to learn about the Eastern Shore. Short walk to town to pick up some needed items at the local pharmacy and on the way back stopped at the olive oil store and bought a couple of interesting bottles. Would have like to check out the SPA, but we decided on Friday to spend Saturday and Sunday nights and they were booked. The staff was generally friendly. It was expensive per night. But for clean and beautiful grounds, a clean room, friendly staff, and views from our room and from the restaurants that included water and boats, I felt it was worth it for our spontaneous road trip from the Philly suburb. We would come back and this time book a sailing activity and a massage. Notes: The big Samsung TV was nice but doesn't allow streaming from my phones and so we had to watch our show on my laptop. Room #2 was great in that it was in the main lodge next to the restaurant and a across from the bar which was very noisy at times. We didn't mind for 2 days, we enjoyed the convenience and drowned at noisy with a sound machine. If we were there for longer, the noise may have gotten old. In summary, we liked it and would visit again."
Greg 2-night trip
Posted 7 hours ago
Inn at Perry Cabin

Find out more about Chesapeake Beach

Five Star Hotels in Chesapeake Beach

There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Chesapeake Beach so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Chesapeake Beach and get ready to be pampered like never before.

Get a Great Deal on 5-Star Hotels in Chesapeake Beach

Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places.

Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town.

Make Your Escape to Chesapeake Beach

The results are in, and Chesapeake Beach 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Chesapeake Beach! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Chesapeake Beach today and settle down in the lap of luxury tomorrow.

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 can vary based on the time of year you travel and how long you plan to stay, among a range of factors. Use our price per night filter and other search tools to score the best rate on a luxurious stay.

  • Search for the lowest price per night from CA $315

What makes a hotel 5 stars in Chesapeake Beach?
Exemplary guest service is at the heart of every 5-star hotel in Chesapeake Beach. From the minute you step through the door, staff cater to your every whim, whether recommending activities or providing in-room beauty treatments. What's more, hotels have to offer upscale amenities to be considered for a 5-star rating. These can include deluxe baths, spa facilities, swimming pools, gourmet kitchens and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Chesapeake Beach?
Use Expedia's filters to find a luxury escape in Chesapeake Beach where most of what you need is included in the price. Next, narrow your results for accommodations that have a 5-star rating and are categorized as "All inclusive." The main thing on the agenda at these stays? Relaxation and indulgence.

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