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4 Stars Hotels in Chestertown, Maryland from CA $282

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Check availability on Chestertown 4 Star Hotels

Top Chestertown 4 Star Hotels

Annapolis Waterfront Hotel, Autograph Collection
Room, 2 Queen Beds, Non Smoking, Balcony

Annapolis Waterfront Hotel, Autograph Collection

4.0 star property
8.8 out of 10, Excellent, (853)
" Very clean, spacious room, friendly staff"
The price is CA $326
CA $372 total
includes taxes & fees
Aug 24 - Aug 25
Annapolis Waterfront Hotel, Autograph Collection
The Inn at Chesapeake Bay Beach Club
Front of property - evening/night

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (407)
"Great location and amenities"
The price is CA $282
CA $348 total
includes taxes & fees
Aug 24 - Aug 25
The Inn at Chesapeake Bay Beach Club
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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.
Sagamore Pendry Baltimore

Sagamore Pendry Baltimore

1715 Thames St., Baltimore, MD
The price is CA $501 per night from Sep 7 to Sep 8
CA $501
CA $645 total
Sep 7 - Sep 8
includes taxes & fees
9.4/10 Exceptional! (1,004 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.

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Top Chestertown Hotel Reviews

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
" Very clean, spacious room, friendly staff"
Alison 2-night trip
Posted 3 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 lock in a 4-star hotel in Chestertown that's within your budget, make use of Expedia's sort and search filters. Browse the available options during your preferred dates and use our pricing filter to set your limit. You can also list your results by the cheapest property first.

  • Search for the lowest price from CA $501

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 great option for your Chestertown break. These kinds of accommodations generally come with loads of useful amenities that make it simple to unpack and recharge — think large beds, bathrobes, restaurants and gyms. Or enjoy even more lavishness at a 5-star hotel designed to indulge you in luxury perks and amenities. Concierge assistance, oversized bathrooms and fine dining are typically featured at these deluxe properties.
Does Chestertown have any 4-star all-inclusive resorts?
Use our "All inclusive" filter to find your dream resort in Chestertown where just about everything is taken care of, from your meals to your room, entertainment and activities. We can also help you find standard 4-star stays in and around this destination.