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

Chesapeake Beach 5 Stars Hotels

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Check availability on Chesapeake Beach 5 Star Hotels

Tonight
Sep 10 - Sep 11
Tomorrow
Sep 11 - Sep 12
This weekend
Sep 11 - Sep 13
Next weekend
Sep 18 - Sep 20

Our top choices for Chesapeake Beach 5-star hotels

Premium bedding, down comforters, in-room safe, desk
Premium bedding, down comforters, in-room safe, desk
Outdoor pool
Golf

1. Inn at Perry Cabin

Inn at Perry Cabin
Downtown St. Michaels
United States
Andrew
NT$20,390
NT$22,429 total
includes taxes & fees
Oct 6 - Oct 7
Inn at Perry Cabin
Seasonal outdoor pool, pool umbrellas, sun loungers
Front of property
Taylor's Suite | Frette Italian sheets, premium bedding, down comforters, WiFi (free)
Frette Italian sheets, premium bedding, down comforters, WiFi (free)

2. The Inn at Tacaro Estate

The Inn at Tacaro Estate
Tracys Landing
United States
James
NT$12,480
NT$14,228 total
includes taxes & fees
Oct 11 - Oct 12
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
NT$4,550
NT$6,098 total
Oct 11 - Oct 12
includes taxes & fees
8.6/10 Excellent! (1,007 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

Inn at Perry Cabin

Inn at Perry Cabin

10/10 Excellent
"It’s so lovely and elegant I almost don’t want to tell people it’s there. Stunning, perfect in every way."
Susan 1-night trip
Posted 1 day 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 NT$6,098
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.

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