4 Stars Hotels in Chestertown, Maryland from CA $356

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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 CA $312
CA $356 total
includes taxes & fees
May 26 - May 27
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 CA $295
CA $362 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 CA $448 per night from May 27 to May 28
CA $448
CA $583 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 harbour.

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

Find out more about Chestertown

If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Chestertown are calling your name. Known for providing first-rate service in amazing locations, each of the Chestertown 4 Stars hotels lets discerning travelers bask in an unforgettable experience.

Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day.

It’s all waiting for you at the top four star hotels in Chestertown. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Chestertown, Maryland, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Chestertown hotels with 4 Stars provide everything you need to unwind in style.

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 $583

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.

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