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

Find 4 Star Hotels in Chestertown, MD from $254

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Check availability on Chestertown 4 Star Hotels

Tonight
Oct 17 - Oct 18
Tomorrow
Oct 18 - Oct 19
Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

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.
A hotel room with a large bed, a chair, a small table, and a view of a body of water.
The exterior of the Annapolis Waterfront Hotel with a clear entrance, large windows, and a bench outside.

1. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
Historic District
United States
William
$223 nightly
$254 total
Nov 1 - Nov 2
Total with taxes and fees
Annapolis Waterfront Hotel, Autograph Collection
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.
A spacious dining area with round tables, high ceilings with ductwork, and a stone fireplace.
A residential area with a garden, a patio with outdoor furniture, and a house with a chimney.
A bar area with multiple seating options, a variety of bottles and glasses on shelves, and a modern chandelier.

2. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
United States
scott
$237 nightly
$263 total
Nov 15 - Nov 16
Total with taxes and fees
The Inn at Chesapeake Bay Beach Club
A modern living room with a staircase, a dining area, and a kitchen in the background.
A red brick building with a black door, a small porch, and two green trash bins.
A kitchen with a black refrigerator, a framed picture on the wall, and a small table with decorative items.
A modern living room with a brown sofa, glass coffee table, and decorative wall art.

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 living room with a brick wall, a fireplace, a sofa, and a coffee table.
A spacious living area with a brick wall, wooden flooring, and a modern sofa set.

4. Rooftop Patio w/ View: Baltimore Retreat

Rooftop Patio w/ View: Baltimore Retreat
Canton
Rooftop Patio w/ View: Baltimore Retreat
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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
$431 nightly
$506 total
Nov 10 - Nov 11
Total with taxes and fees
Pendry Baltimore
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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.

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
A lakeside town with a marina, a bridge, and a mix of residential and commercial buildings.

Top Chestertown Hotel Reviews

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

10/10 Excellent
"The staff was awesome. Very professional and helpful. Our room was cleaned and well maintained. The food was great and the spa service was awesome as well."
Lamont 3-night trip
Posted 2 days ago
The Inn at Chesapeake Bay Beach Club
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"Perfect place to stay! Classy. Clean comfortable amazing staff"
Nila 2-night trip
Posted 3 days ago
Annapolis Waterfront Hotel, Autograph Collection

Find out more about Chestertown

Chestertown Four Star Hotel Information

When you need to book a room with luxurious amazing amenities and the best rates, the 4 star hotels in Chestertown, Maryland are incredible options. Known for their extra perks, first-rate service, and fantastic locations, each of the Chestertown 4 star hotels offers the ultimate experience for globe-trotting travelers. Relax in your expertly designed room. Kick back with around-the-clock room service.

Get a good night’s sleep with the ultra-plush bedding, and freshen up in the morning with designer-inspired body products. It’s all available when you stay at one of the top book a four star hotels in Chestertown. What’s more, thanks to Expedia you might even score a cheap great deal on a 4 star hotel in Chestertown, Maryland, areas near the hottest attractions, so you can plan a sightseeing adventure and take advantage of unbeatable discounts in one fell swoop.

Whether you’re putting together a serene getaway or want to revel in the most vibrant entertainment district, 4 star Chestertown hotels offer everything your heart desires.

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Chestertown?
With Expedia's handy filter tool, landing a terrific deal on a 4-star hotel in Chestertown just got easier. Start by entering your chosen arrival date and length of your getaway. Then list the results by price and choose a property that best matches your budget and style.
  • Search for the lowest price from $506
What's the difference between 5-star and 4-star hotels in Chestertown?
If you decide to vacation at a 4-star hotel in Chestertown, you'll typically find loads of conveniences to make sure you're comfortable, such as a restaurant, pool and gym. You can look forward to excellent service and upscale surroundings. Opt for a 5-star hotel and you'll have access to a few more bells and whistles — think on-site spas, around-the-clock concierge and opulent turndown services. You'll most likely get extra amenities and premium services at a 5-star stay, but both are fabulous options for luxury guests.
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.

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