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

Compare and book 4 Star hotels in Chestertown, Maryland

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Check availability on Chestertown 4 Star Hotels

This weekend
6 Nov - 8 Nov
Next weekend
13 Nov - 15 Nov

Our top choices for Chestertown 4-star hotels

A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

1. 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, (511 reviews)
"Great property super friendly, helpful staff."
United States
scott
The price is 4.733.002 ₫
5.906.957 ₫ total
includes taxes & fees
2 Dec - 3 Dec
The Inn at Chesapeake Bay Beach Club
A balcony with a table set for two, overlooking a marina with boats.

2. Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (1,000 reviews)
"Staff was Great, Great Location. Nice Restaurant Bartender was great!"
United States
Donna
The price is 5.731.999 ₫
6.534.479 ₫ total
includes taxes & fees
29 Nov - 30 Nov
Annapolis Waterfront Hotel, Autograph Collection
A modern living room with a staircase, a dining area, and a kitchen in the background.

3. Hudson house

Hudson house
4.0 star property
Canton
7.6 out of 10, Good, (5 reviews)
"The condo was really nice and clean"
United States
Thelma
Hudson house
A modern kitchen with white cabinetry, granite countertops, and stainless steel appliances.

4. 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
The price is 9.852.675 ₫ per night from 30 Nov to 1 Dec
9.852.675 ₫
12.634.963 ₫ total
30 Nov - 1 Dec
includes taxes & fees
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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 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

10/10 Excellent
"Staff was Great, Great Location. Nice Restaurant Bartender was great!"
Donna 1-night trip
Posted 2 days 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 12.634.963 ₫

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 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 holiday bliss in Chestertown is as easy as entering your travel details and selecting our "All inclusive" filter. Stay and play where just about everything is already taken care of like your accommodation, meals and activities, or choose a standard 4-star resort in or around this top destination.