Explore top 2025 5 Star Hotels in Chesapeake Beach

Name: Inn at Perry Cabin
Price range: $653 total

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Top Chesapeake Beach 5 Star hotels

Inn at Perry Cabin

308 Watkins Ln, St. Michaels, MD

$594 nightly

$653 total

Oct 1 - Oct 2

Total with taxes and fees

This luxury hotel features a golf course, a full-service spa, and a marina. Families will appreciate complimentary bicycles, kid-friendly dining, and in-room ...

The Inn at Tacaro Estate

6220 Town Point Rd, Tracys Landing, MD

Fully refundableReserve now, pay when you stay

$355 nightly

$405 total

Sep 14 - Sep 15

Total with taxes and fees

This bed & breakfast features a seasonal outdoor pool and a hot tub. There's no skimping on freebies - guests receive free full breakfast, free WiFi, and free ...

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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.

Chesapeake Beach Resorts & 5 Star Hotels

Looking for your own little slice of heaven during your next trip? Check out all the best 5-star hotels in Chesapeake Beach to make sure your trip is as extravagantly comfortable as you expect.

Whether you plan on staying in your room the whole time or getting out and enjoying the city, you’ll be living the life while staying at your luxury accommodation. With so many amenities at your beck and call, you might try to turn your stay into a staycation!

Many of the 5-star hotels have award-winning restaurants you can dine at, as well as plush bedding and a concierge service to take care of your every need. Most also offer pools and modern fitness centers, not to mention high-speed Wi-Fi.

For your next trip, book a hotel that can be your own little hideaway, whether you’re in town for business or leisure. Chesapeake Beach 5-star hotels provide you with all the comforts and amenities you expect from a sophisticated hotel, with a staff that’s happy to ensure you have everything you need to feel at home.

Whether you’re a first-time guest, or you’ve stayed in 5-star hotels in Chesapeake Beach before, you’ll have no shortage of options to choose from on your next trip when you book with Travelocity. Browse our vast selection and find great deals on luxury lodging.