Chesapeake Beach 5 Stars Hotels

  • 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
26 Apr - 27 Apr
Tomorrow
27 Apr - 28 Apr
Next weekend
1 May - 3 May
In two weeks
8 May - 10 May

Our top choices for Chesapeake Beach 5-star hotels

Breakfast, lunch, dinner served; sea views

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (380 reviews)
"The Inn at Perry Cabin was a great option "
United States
Kate
The price is HK$4,725
HK$5,197 total
includes taxes & fees
29 Apr - 30 Apr
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, (13 reviews)
"Beautiful place to stay with a breathtaking view of the Chesapeake Bay from a hilltop. Has a speakeasy bar in the basement which takes you back to the 1920’s. Breakfast is very subperb!"
United States
Philip
The price is HK$1,989
HK$2,268 total
includes taxes & fees
28 Apr - 29 Apr
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 HK$1,051 per night from 29 Apr to 30 Apr
HK$1,051
HK$1,323 total
29 Apr - 30 Apr
includes taxes & fees
8.6/10 Excellent! (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
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
"Food, drinks and staff were all awesome. They had good bikes to borrow and ride into town on if you wanted, “don’t worry about locking them, nobody will take them”. They also would drive you, and pick you up if you wanted a ride to town. Everything about the experience was 1st class. Room was very clean. Wait staff were all professional. Their gift shop was stocked with high quality items. Even the grounds keepers and maintenance staff were polite. They all treat you like royalty. St. Michael’s was absolutely beautiful."
Rudie 2-night trip
Posted 2 weeks 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 HK$1,323

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.

Explore a world of travel with Expedia