Compare and book 4 Star hotels in Chestertown, Maryland
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14 Aug - 16 AugOur top choices for Chestertown 4-star hotels
1. Annapolis Waterfront Hotel, Autograph Collection
Annapolis Waterfront Hotel, Autograph CollectionHistoric District
Stacey
5.429.676 ₫
6.189.831 ₫ total
includes taxes & fees
7 Sept - 8 Sept
5.660.727 ₫
6.951.207 ₫ total
includes taxes & fees
31 Aug - 1 Sept
4. Rooftop Patio w/ View: Baltimore Retreat
Rooftop Patio w/ View: Baltimore RetreatCanton
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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
1715 Thames St. Baltimore MD
9.014.520 ₫
11.669.872 ₫ total
7 Sept - 8 Sept
includes taxes & fees
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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.
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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 11.669.872 ₫
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.