Hotels in Chestertown from $92 - Find Cheap Hotels with momondo

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Top Hotels in Chestertown

Find the perfect hotel for your stay in Chestertown

Price

$91

$1,472

Review Score

Hotel class

Hostels and cheap hotels in Chestertown

These hotels and hostels usually make for a cheap way to stay in Chestertown

Red Roof Inn & Suites Chestertown

160 Scheeler Road, Chestertown, MD, United States

6.9

$92

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The Lodge at Great Oak Landing

Chestertown, MD, United States

$148

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Driftwood Inn

609 Washington Avenue, Chestertown, MD, United States

4.7

$95

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First Floor Studio Apartment in Historic Chestertown

Chestertown, MD, United States

9.5

$187

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Comfort Inn and Suites Chestertown

150 Scheeler Road, Chestertown, MD, United States

8.0

$124

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3 Mi to Washington College! Updated Home w/ Patio

Chestertown, MD, United States

$228

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Get the best value hotel in Chestertown

These Chestertown hotels have the best prices for their ratings

Comfort Inn and Suites Chestertown

150 Scheeler Road, Chestertown, MD, United States

8.0

$124

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Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Chestertown, MD, United States

10.0

$259

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Red Roof Inn & Suites Chestertown

160 Scheeler Road, Chestertown, MD, United States

6.9

$92

View Deal

Driftwood Inn

609 Washington Avenue, Chestertown, MD, United States

4.7

$95

View Deal

First Floor Studio Apartment in Historic Chestertown

Chestertown, MD, United States

9.5

$187

View Deal

Historic Downtown Garden Oasis with Private Patio

Chestertown, MD, United States

9.9

$327

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Useful insights on Chestertown hotels

Get a quick overview on price and accommodation trends for your visit in Chestertown

Lowest Hotel Price	$92
Most Popular Hotel (5-star)	Brampton 1860
Hotels Near Airport	2055

The cheapest price for a room in Chestertown found in the last 7 days is $92/night. This rate is available with Red Roof Inn & Suites Chestertown, a 2-star hotel.

Travel with comfort when booking a room with Brampton 1860, the most popular 5-star hotel in Chestertown.

There are 2,055 hotels in Chestertown close to Philadelphia. Philadelphia Airport Marriott is the nearest with a distance of 0.4 km from this airport.

When to book a hotel in Chestertown

Check out the information below to find the best deal on a hotel room in Chestertown

What is the cheapest day of the week to book a hotel in Chestertown?

Monday is the cheapest day of the week to stay in Chestertown, with an average cost of $157/night. The most expensive day to book is Friday with an average cost of $284/night.

What is the cheapest month to book a hotel in Chestertown?

The cheapest month to stay in Chestertown is November, with an average cost of $131/night. The expected decrease to stay in November is 48%. The most expensive month to stay in Chestertown is October, with an average cost of $484/night. This is an expected increase of 89%.

Information about staying in Chestertown

Read these important travel tips before booking a hotel in Chestertown

How much does a hotel cost in Chestertown, MD?

On average, rooms will be priced around $165 per night when booking a hotel in Chestertown, MD; however the price you pay for your room will vary significantly depending on seasonality, location and facilities.

When is the best time to book a hotel in Chestertown, MD?

Room prices for hotels in Chestertown, MD can be as much as 49% lower in the month of November. So this is a great time to book and save money.

Which day is cheapest to stay in Chestertown, MD?

At the moment the cheapest day to stay in a hotel in Chestertown, MD is Sunday, with Thursday being the most expensive.

Based on the weather in Chestertown, what attractions are popular during May?

With good temperatures around 18 °C and just a moderate chance of expected rainfall, those staying at a hotel in Chestertown should consider visiting popular establishments near Chestertown.

How many operators does momondo search for hotels in Chestertown?

The number of operators available for hotels in Chestertown is 45 as of April 2026.

When did momondo last update prices for hotels in Chestertown?

Prices for hotels in Chestertown refresh daily.

Why use momondo?

Why should I book accommodation in Chestertown through momondo?

Booking accommodation or a hotels in Chestertown is made easy with momondo. We are free to use and there are no hidden costs or fees. momondo compares hundreds of websites and gives you all your Chestertown hotels and accommodation options in one place.

How does momondo help me find a great place to stay in Chestertown?

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