An aerial view of a town with a river, buildings, and surrounding greenery.

4 Stars Hotels in Chestertown, Maryland from CA $334

  • 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

Tonight
Sep 22 - Sep 23
Tomorrow
Sep 23 - Sep 24
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

Our top choices for Chestertown 4-star hotels

A balcony with a table set for two, overlooking a marina with boats.
A waterfront property with a docked boat, a tall building with balconies, and a church spire in the background.
The exterior of the Annapolis Waterfront Hotel with a clear entrance, large windows, and a bench outside.
A waterfront area with boats docked, a clear sky, and buildings in the background.

1. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
Historic District
United States
William
CA $336
CA $383 total
includes taxes & fees
Sep 30 - Oct 1
Annapolis Waterfront Hotel, Autograph Collection
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.
A bar area with multiple seating options, a variety of bottles and glasses on shelves, and a modern chandelier.
A residential area with a garden, a patio with outdoor furniture, and a house with a chimney.
A spacious dining area with round tables, high ceilings with ductwork, and a stone fireplace.

2. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
United States
scott
CA $268
CA $334 total
includes taxes & fees
Oct 19 - Oct 20
The Inn at Chesapeake Bay Beach Club
A modern living room with a staircase, a dining area, and a kitchen in the background.
A modern kitchen with stainless steel appliances, wooden cabinets, and a tiled floor.
A modern living room with a brown sofa, glass coffee table, and decorative wall art.
A kitchen with a black refrigerator, a framed picture on the wall, and a small table with decorative items.

3. Hudson house

Hudson house
Canton
United States
Thelma
Hudson house
A modern kitchen with white cabinetry, granite countertops, and stainless steel appliances.
A bedroom with a large bed, a ceiling fan, and a nightstand with a lamp.
A modern living room with a brick wall, wooden flooring, and a dining area with wicker chairs and a round table.
A living room with a brick wall, a fireplace, a sofa, and a coffee table.

4. Rooftop Patio w/ View: Baltimore Retreat

Rooftop Patio w/ View: Baltimore Retreat
Canton
Rooftop Patio w/ View: Baltimore Retreat
Save an average of 15% on thousands of hotels when you're signed in

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
CA $561
CA $717 total
Oct 22 - Oct 23
includes taxes & fees
Pendry Baltimore
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.
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 harbour.

See all hotels in Chestertown
A lakeside town with a marina, a bridge, and a mix of residential and commercial buildings.

Top Chestertown Hotel Reviews

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good
"The view from our room was incredible. The property is clean and the beds comfortable. For the price, however, the only thing that justifies it is the view and location. There are 2 restaurants- Marmo was disappointing and overpriced. The cantina was great. Unfortunately, they take up all of the waterfront dock area, so there is really nowhere else to gather in the hotel to enjoy the water if you just want to sit and visit or play a game, or some such. (The balconies were too small for anything except a cup of coffee). And since the restaurants are open to the public the area is packed all the time. Otherwise, being an older hotel, there really aren't any special amenities. No spa or pool. nothing else special about it. And those terrible nespresso machines in the room. I just want a regular cup of coffee. Parking is overpriced- we hoofed it to a garage a few blocks away for significantly less per day."
Karen 3-night trip
Posted 5 hours ago
Annapolis Waterfront Hotel, Autograph Collection

Find out more about Chestertown

If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Chestertown are calling your name. Known for providing first-rate service in amazing locations, each of the Chestertown 4 Stars hotels lets discerning travelers bask in an unforgettable experience.

Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day.

It’s all waiting for you at the top four star hotels in Chestertown. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Chestertown, Maryland, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Chestertown hotels with 4 Stars provide everything you need to unwind in style.

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Chestertown?
To lock in a 4-star hotel in Chestertown that's within your budget, make use of Expedia's sort and search filters. Browse the available options during your preferred dates and use our pricing filter to set your limit. You can also list your results by the cheapest property first.
  • Search for the lowest price from CA $717
What's the difference between 5-star and 4-star hotels in Chestertown?
Offering a friendly traveller experience and upmarket décor, 4-star hotels are a great option for your Chestertown break. These kinds of accommodations generally come with loads of useful amenities that make it simple to unpack and recharge — think large beds, bathrobes, restaurants and gyms. Or enjoy even more lavishness at a 5-star hotel designed to indulge you in luxury perks and amenities. Concierge assistance, oversized bathrooms and fine dining are typically featured at these deluxe properties.
Does Chestertown have any 4-star all-inclusive resorts?
Use our "All inclusive" filter to find your dream resort in Chestertown where just about everything is taken care of, from your meals to your room, entertainment and activities. We can also help you find standard 4-star stays in and around this destination.

Explore a world of travel with Expedia