An aerial view of a town with a river, buildings, and surrounding greenery.

Chestertown 4 Stars Hotels

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Check availability on Chestertown 4 Star Hotels

Tonight
Aug 8 - Aug 9
Tomorrow
Aug 9 - Aug 10
Next weekend
Aug 14 - Aug 16
In two weeks
Aug 21 - Aug 23

Our top choices for Chestertown 4-star hotels

Private beach nearby, sun loungers, beach volleyball
Property grounds
Private beach nearby, sun loungers, beach volleyball
Reception

1. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
Chestertown
United States
Nicola
NT$3,483
NT$3,982 total
includes taxes & fees
Aug 16 - Aug 17
The Lodge at Great Oak Landing
Free daily full breakfast
Desk, laptop workspace, blackout drapes, iron/ironing board
Point of interest
Lobby

2. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
United States
Deanna
NT$3,457
NT$3,837 total
includes taxes & fees
Aug 31 - Sep 1
Comfort Inn & Suites Chestertown
Lobby lounge
Lobby lounge
Suite, Multiple Beds, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board
Suite, Multiple Beds, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board

3. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
Chestertown
United States
Anasmel
NT$2,032
NT$2,255 total
includes taxes & fees
Aug 16 - Aug 17
Red Roof Inn & Suites Chestertown
Front of property - evening/night
TV
Front of property
Lobby

4. Driftwood Inn

Driftwood Inn
Chestertown
United States
Daryl
NT$2,048
NT$2,273 total
includes taxes & fees
Aug 15 - Aug 16
Driftwood Inn
Property grounds
Private beach, kayaking, rowing
Exterior
Deluxe Suite, 1 King Bed, Fireplace (Roese) | Premium bedding, in-room safe, desk, iron/ironing board

5. Great Oak Manor

Great Oak Manor
Chestertown
United States
Scott
Great Oak Manor
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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
NT$11,113
NT$14,386 total
Sep 7 - Sep 8
includes taxes & fees
Pendry Baltimore
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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 harbor.

See all hotels in Chestertown
A lakeside town with a marina, a bridge, and a mix of residential and commercial buildings.

Top Chestertown Hotel Reviews

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 NT$14,386
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.

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