Find 4 Star Hotels in Chestertown, MD from AED 729

  • 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 Chestertown 4 Star Hotels

Our top choices for Chestertown 4-star hotels

Premium bedding, down comforters, pillowtop beds, in-room safe

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (898 reviews)
"Great location, nice and clean "
United States
Micah
The price is AED 684
AED 779 total
includes taxes & fees
1 Feb - 2 Feb
Annapolis Waterfront Hotel, Autograph Collection
Front of property - evening/night

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (434 reviews)
"Amazing rooms and service!"
United States
Alicia
The price is AED 573
AED 729 total
includes taxes & fees
1 Feb - 2 Feb
The Inn at Chesapeake Bay Beach Club
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Chestertown.
Pendry Baltimore

Pendry Baltimore

1715 Thames St. Baltimore MD
The price is AED 1,219 per night from Feb 17 to Feb 18
AED 1,219
AED 1,584 total
17 Feb - 18 Feb
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
Still don't see what you're looking for?
See all properties in Chestertown.
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 Chestertown

Colonial charm meets Chesapeake Bay beauty in this historic waterfront town where 18th-century buildings house art galleries and boutiques. Rent kayaks to explore the Chester River or time your visit for the Downrigging Weekend Festival when tall ships transform the harbor.

See all hotels in Chestertown
Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

Top Chestertown Hotel Reviews

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"Very welcoming and room very clean."
Paola 2-night trip
Posted 2 weeks ago
Annapolis Waterfront Hotel, Autograph Collection

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Chestertown?
To book a 4-star hotel in Chestertown that's within your budget, take advantage of Expedia's filters. Take a look at the availability during your getaway dates and use our pricing filter to set your limit. You can also list your results by the most wallet-friendly option first.

  • Search for the lowest price from AED 1,584

What's the difference between 5-star and 4-star hotels in Chestertown?
Offering a friendly traveler experience and upmarket décor, 4-star hotels are a terrific option for your Chestertown trip. These types of stays generally feature lots of handy amenities that make it easy to unpack and recharge — think complimentary bathrobes, pools and gyms. Or enjoy even more lavishness at a 5-star hotel designed to spoil you with high-end perks and amenities. Concierge assistance, complimentary toiletries and world-class dining are typically included at these plush retreats.
Does Chestertown have any 4-star all-inclusive resorts?
Finding your dream hotel in Chestertown is as easy as typing in your travel details and clicking on our "All inclusive" filter. Stay and play where almost everything is already taken care of like your accommodations, meals and activities, or go for a standard 4-star resort in or around this top destination.

Explore a world of travel with Expedia