Find 4 Star Hotels in Chestertown, MD from SAR 679

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Check prices for these dates

Tonight
8 Nov - 9 Nov
Tomorrow
9 Nov - 10 Nov
Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 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, (512 reviews)
"Great property super friendly, helpful staff."
United States
scott
The price is SAR 680
SAR 850 total
includes taxes & fees
9 Dec - 10 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 SAR 808
SAR 921 total
includes taxes & fees
23 Nov - 24 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 living room with a sectional sofa, a coffee table, and two framed artworks on the wall.

4. Rooftop Patio w/ View: Baltimore Retreat

Rooftop Patio w/ View: Baltimore Retreat
4.0 star property
Canton
Rooftop Patio w/ View: Baltimore Retreat

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 SAR 679

What's the difference between 5-star and 4-star hotels in Chestertown?

Offering a friendly traveler 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 vacation 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 accommodations, meals and activities, or choose a standard 4-star resort in or around this top destination.