Compare and book 5 Star hotels in Chesapeake Beach, Maryland

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chesapeake Beach 5 Star Hotels

Tonight
8 Mar - 9 Mar
Tomorrow
9 Mar - 10 Mar
Next weekend
13 Mar - 15 Mar
In two weeks
20 Mar - 22 Mar

Our top choices for Chesapeake Beach 5-star hotels

Premium bedding, down duvets, in-room safe, desk

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (374 reviews)
"Fantastic resort; beautiful with lots of great history. Highly recommend the historic walking tour with Jay. "
United States
Joseph
The price is 9.712.287 ₫
10.683.516 ₫ total
includes taxes & fees
9 Mar - 10 Mar
Inn at Perry Cabin
Seasonal outdoor pool, pool umbrellas, pool loungers

The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.4 out of 10, Exceptional, (12 reviews)
"Wonderful experience Felt like being in good friends home without having to help with the dishes Luxurious stay Recommend *****"
United States
Todd
The Inn at Tacaro Estate
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 2.667.144 ₫ per night from 15 Mar to 16 Mar
2.667.144 ₫
3.484.809 ₫ total
15 Mar - 16 Mar
includes taxes & fees
8.4/10 Very Good! (1,005 reviews)
Still don't see what you're looking for?
See all properties in Chesapeake Beach.
You can also use these popular filters to refine your search.
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 fossilised shark teeth along the Bay's ancient shoreline.

See all hotels in Chesapeake Beach
Boardwalk along the Chesapeake Bay.
Photo by Ronanne Vinson
Open Photo by Ronanne Vinson

Top Chesapeake Beach Hotel Reviews

Inn at Perry Cabin

Inn at Perry Cabin

10/10 Excellent
"We had a great stay, hotel was very clean and food was great"
Jonathan 1-night trip
Posted 2 months ago
Inn at Perry Cabin

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 depends on things like when you plan to travel and the length of your escape. A top tip for scoring an awesome deal? Use our pricing filters to compare all of the available options for your preferred dates.

  • Search for the lowest price per night from 3.484.809 ₫

What makes a hotel 5 stars in Chesapeake Beach?
Flawless guest service is integral to every 5-star hotel in Chesapeake Beach. From the moment you enter the lobby, staff are at your beck and call, whether arranging customised tours or providing in-room massage treatments. In addition, hotels have to feature upscale conveniences to obtain a 5-star rating. These can include luxury toiletries, an on-site spa, swimming pools, fine dining restaurants and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Chesapeake Beach?
Expedia's filter tool is the quickest way to search for exactly what you're looking for. Select "5-star" and "All inclusive" to see the most luxurious hotels in Chesapeake Beach where your meals, room, entertainment and activities are included in the price. At these stays, your holiday is pure indulgence from the moment you enter the lobby.