Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

4 Stars Hotels in Chestertown, Maryland from CA $390

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Check availability on Chestertown 4 Star Hotels

This weekend
Jun 26 - Jun 28
Next weekend
Jul 3 - Jul 5

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, (938 reviews)
"Definitely the view of the harbor from our room and how all the stores and restaurants were in walking distance"
United States
Salvatore
The price is CA $348
CA $396 total
includes taxes & fees
Jul 1 - Jul 2
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, (464 reviews)
"Wonderful stay! Everything was amazing..,the staff, rooms, Knoxie’s Table, the spa! Couldn’t have asked for a better stay. I’ll definitely return."
United States
Damika
The price is CA $319
CA $390 total
includes taxes & fees
Jul 6 - Jul 7
The Inn at Chesapeake Bay Beach Club
Printers

Hudson house

Hudson house
4.0 star property
Canton
10.0 out of 10, Exceptional, (2 reviews)
"The condo was really nice and clean"
United States
Thelma
Hudson house
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 $481 per night from Jul 12 to Jul 13
CA $481
CA $624 total
Jul 12 - Jul 13
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

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

10/10 Excellent
"Wonderful facility. Enjoyed the on site amenities. The garden was an interesting twist.Stayed in the Barn, a little tight for two people but well designed space. I would recommend if in the area."
Amanda 2-night trip
Posted 23 hours ago
The Inn at Chesapeake Bay Beach Club
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good
"When we arrived people were still checking out because of the problem with the elevators. So we have to wait for the room to be cleaned. We booked a handicap room but was giving a standard room I called down to the desk and they did move us to a handicap room. The Restaurant was closed for remodeling. One of the two elevators was not working. The hallways were hot. The a/c was working in our room just fine. It could be a nice place to stay. The location is great for someone that wants to shop etc. I felt it was a little pricey."
William 2-night trip
Posted 5 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 $624

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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