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

Find 4 Star Hotels in Chestertown, MD from $217

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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, (946 reviews)
"Definitely the view of the harbor from our room and how all the stores and restaurants were in walking distance"
United States
Salvatore
$190 nightly
The price is $217
Aug 2 - Aug 3
Total with taxes and fees
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, (468 reviews)
"Wonderful stay! Everything was amazing..,the staff, rooms, Knoxie’s Table, the spa! Couldn’t have asked for a better stay. I’ll definitely return."
United States
Damika
$258 nightly
The price is $287
Aug 2 - Aug 3
Total with taxes and fees
The Inn at Chesapeake Bay Beach Club
Printers

Hudson house

Hudson house
4.0 star property
Canton
10.0 out of 10, Exceptional, (2 reviews)
"The condo was really nice and clean"
United States
Thelma
Hudson house
Apartment (4 Bedrooms) | Interior

Rooftop Patio w/ View: Baltimore Retreat

Rooftop Patio w/ View: Baltimore Retreat
4.0 star property
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
$455 nightly
The price is $535 total per night from Aug 16 to Aug 17
$535 total
Aug 16 - Aug 17
Total with taxes and fees
9.4/10 Exceptional! (1,002 reviews)
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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 restaurant was wonderful and so was the staff. The grounds were gorgeous and interesting."
suzanne 1-night trip
Posted 3 weeks ago
The Inn at Chesapeake Bay Beach Club

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 $535

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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