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Check availability on Chestertown 4 Star Hotels

Our top choices for Chestertown 4-star hotels

Premium bedding, down duvets, pillow-top 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, (916 reviews)
"Great waterfront room with roomy balcony. Gym was nice also. Can't wait for the var and restaurants to open."
United States
Douglas
The price is 6.556.668 ₫
7.474.602 ₫ total
includes taxes & fees
12 Apr - 13 Apr
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, (447 reviews)
"Very clean room, staff was very nice. "
United States
Byron
The price is 4.891.918 ₫
6.099.915 ₫ total
includes taxes & fees
12 Apr - 13 Apr
The Inn at Chesapeake Bay Beach Club
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
The price is 9.163.536 ₫ per night from 6 May to 7 May
9.163.536 ₫
11.850.189 ₫ total
6 May - 7 May
includes taxes & fees
9.4/10 Exceptional! (1,000 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 harbour.

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

6/10 Okay
"All restaurants onsite were not open! We had to order from a restaurant nearby but it really was not set up properly for room service. We had to go there to order and pickup and they were not really sure of the process for hotel guests so we just paid with a separate CC. Breakfast was essentially not available and we had to go to town to pickup breakfast as well. The heat in our room did not work for the first day and night! The hotel knew they had a situation going on but did not say anything to us in advance and the hotel was sold-out.At first they suggested a space heater but then another supervisor came on duty and told us those were not premitted - and we could understand why. It was fixed by our second night. We were told we would get a credit toward the first night but we did not?"
Nancy 2-night trip
Posted 11 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 11.850.189 ₫

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.