Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

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Check availability on Chestertown 4 Star Hotels

This weekend
26 Jun - 28 Jun
Next weekend
3 Jul - 5 Jul

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, (938 reviews)
"Definitely the view of the harbor from our room and how all the stores and restaurants were in walking distance"
United States
Salvatore
The price is 7.605.902 ₫
8.670.728 ₫ total
includes taxes & fees
1 Jul - 2 Jul
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, (464 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
The price is 5.937.588 ₫
7.260.253 ₫ total
includes taxes & fees
6 Jul - 7 Jul
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
The price is 8.842.848 ₫ per night from 13 Jul to 14 Jul
8.842.848 ₫
11.472.806 ₫ total
13 Jul - 14 Jul
includes taxes & fees
9.4/10 Exceptional! (1,007 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

8/10 Good
"When we arrived people were still checking out because of the problem with the elevators. So we have to wait for the room to be cleaned. We booked a handicap room but was giving a standard room I called down to the desk and they did move us to a handicap room. The Restaurant was closed for remodeling. One of the two elevators was not working. The hallways were hot. The a/c was working in our room just fine. It could be a nice place to stay. The location is great for someone that wants to shop etc. I felt it was a little pricey."
William 2-night trip
Posted 5 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 11.472.806 ₫

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.