Somewhere over the rainbow... Terrific view on the plane back to the North.

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Explore beach hotels in Chestertown, MD from $126

Name: Comfort Inn & Suites Chestertown
Price range: $126 total
Rating: 8.4

Top Chestertown Beach Resorts & Hotels

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Chestertown

This vacation home featured laundry facilities and barbecue grills.

9.8/10 Exceptional! (61 reviews)

Travelers like: close to beach, beach towels

Travelers say...

"The house and hospitality exceeded all expectations! We had a wonderful long weekend away and would definitely return. The kids especially loved fishing, kayaking, and the paddle boat. The farmer’s market was enjoyable Saturday morning, too. We had beautiful weather for yard games and the fire pit. ..."

Reviewed on Sep 1, 2025

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Comfort Inn & Suites Chestertown

150 Scheeler Road, Chestertown, MD

Fully refundableReserve now, pay when you stay

$114 nightly

$126 total

Sep 17 - Sep 18

Total with taxes and fees

This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will ...

8.4/10 Very Good! (813 reviews)

"The room was spacious and very quiet."

Reviewed on Sep 6, 2025

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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.

Beach Condos in Chestertown

BEACH WITHOUT THE BUSTLE

Betterton Beach

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9.8/10 Exceptional! (34 reviews)

Beach Villas in Chestertown

Secluded Waterfront Retreat 2 bed 1 1/2 baths private guest house w Pool & Beach

White Marsh

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10/10 Exceptional! (9 reviews)

How to find the best Chestertown beach hotels?

We have 874 honest, unfiltered reviews from genuine customers you can check out, with an average review rating of 9.1.

How can I find Chestertown beach hotels with nice views?

Use our ocean view filter to see the Chestertown beach hotels that offer spectacular views. From cliffside panoramas to beach view hotels with rooms overlooking the sand. Check out poolside and tranquil garden views, too.

How much does it cost to stay in a beach hotel in Chestertown?

Currently, we have resorts and hotels in Chestertown on the beach going from $126 a night to $126 for top-end luxury. Prices vary depending on your travel dates, amenities, and neighborhood.

How do I find Chestertown beach hotels that are good for families?

Filter your search results by clicking on the family friendly filter to see kid-friendly amenities and activities. From beach resorts with kids’ clubs to beachfront hotels offering fun watersports—you have plenty of choice.

Why should I book my beach hotel in Chestertown with Travelocity?

With great deals on a vast selection of Chestertown beachfront hotels, 24/7 customer service, and the ability to bundle your hotel, flights, and car rental to save more—Travelocity makes it easy.

Do any beach hotels in Chestertown have a pool?

Many Chestertown hotels on the beach have pools. You can choose which amenities you want and use our pool filter to see the Chestertown beach hotels that have pools on site.

When is the best time to stay in a beach hotel in Chestertown?

The best time to visit Chestertown for local events and activities is .

Are there cheap beach hotels in Chestertown?

Prices for Chestertown beach hotels currently start at just $126 a night. With 4 Chestertown beach hotels to choose from, you have stacks of tempting options, whatever your budget.

What are some great things to do in Chestertown by the beach?

Enjoy swimming, reading, and sunbathing on the beach in Chestertown. There’s also action-packed beach fun and watersport adventures, too. Check each hotel’s information section to find out what’s available.

How can I find the best beach hotels deals in Chestertown?

Pop in your travel dates and hit search and hunt though our fantastic deals on Chestertown beach resorts and beachfront hotels. Download the free Travelocity appOpens in a new window for awesome member discounts.