Chestertown 4 Stars Hotels

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Check availability on Chestertown 4 Star Hotels

Tonight
May 8 - May 9
Tomorrow
May 9 - May 10
This weekend
May 8 - May 10
Next weekend
May 15 - May 17

Our top choices for Chestertown 4-star hotels

Premium bedding, down comforters, pillowtop 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, (926 reviews)
"Clean room. View was great! Staff was nice."
United States
Marie
The price is NT$7,819
NT$8,913 total
includes taxes & fees
May 25 - May 26
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, (453 reviews)
"Beautiful Boutique Hotel on the eastern shore right over the Bay bridge great restaurant Little market that’s amazing nice spa and very pretty and accommodating hotel would highly recommend it! "
United States
Kimberly
The price is NT$6,772
NT$8,315 total
includes taxes & fees
May 11 - May 12
The Inn at Chesapeake Bay Beach Club
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 NT$10,300 per night from May 27 to May 28
NT$10,300
NT$13,393 total
May 27 - May 28
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 harbor.

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

10/10 Excellent
"After a long day of travel, we decided the same day to book a stay in Annapolis as a middle point in our road trip. The hotel was so beautiful from the outside and just as lovely inside. I complimented both of the main desk staff members at check in and check out, it was notable how friendly and accommodating they were! My 6 year old said to me “this place has really great vibes”. 😂 if you’re looking for a conveniently located hotel in Annapolis with a nice harbor view and warm coastal energy, this is your place! "
Cate 1-night trip
Posted 2 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 NT$13,393

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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