Hotels in Chestertown from £44 - Find Cheap Hotels with momondo

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Top hotels in Chestertown

Find the perfect hotel for your stay in Chestertown

Price

£43

£952

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

6.7

£44

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7344695

The Lodge at Great Oak Landing

Chestertown, MD, United States

£79

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282796

Driftwood Inn

609 Washington Avenue, Chestertown, MD, United States

5.3

£50

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114951

First Floor Studio Apartment in Historic Chestertown

Chestertown, MD, United States

9.5

£101

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1070483610

Comfort Inn and Suites Chestertown

150 Scheeler Road, Chestertown, MD, United States

8.0

£73

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7633796

3 Mi to Washington College! Updated Home w/ Patio

Chestertown, MD, United States

7.0

£134

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11313280

Get the best value hotel in Chestertown

These Chestertown hotels have the best prices for their ratings

Red Roof Inn & Suites Chestertown

160 Scheeler Road, Chestertown, MD, United States

6.7

£44

View Deal

7344695

First Floor Studio Apartment in Historic Chestertown

Chestertown, MD, United States

9.5

£101

View Deal

1070483610

Comfort Inn and Suites Chestertown

150 Scheeler Road, Chestertown, MD, United States

8.0

£73

View Deal

7633796

Historic Downtown Garden Oasis with Private Patio

Chestertown, MD, United States

9.9

£159

View Deal

10400370

Driftwood Inn

609 Washington Avenue, Chestertown, MD, United States

5.3

£50

View Deal

114951

Circa 1900 Home in the Heart of Historic Downtown Chestertown

Chestertown, MD, United States

10.0

£248

View Deal

7630388

Useful insights on Chestertown hotels

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

Lowest Hotel Price	£44
Most Popular Hotel (5-star)	Brampton Bed And Breakfast Inn
Hotels Near Airport	2420

The cheapest price for a room in Chestertown found in the last 7 days is £44/night. This rate is available with Red Roof Inn & Suites Chestertown, a 2-star hotel.

Travel with comfort when booking a room with Brampton Bed And Breakfast Inn, the most popular 5-star hotel in Chestertown.

There are 2,420 hotels in Chestertown close to Philadelphia. Philadelphia Airport Marriott is the nearest with a distance of 0.3 mi 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?

Sunday offers the lowest rates for staying in Chestertown, with an average cost of £64 per night. In contrast, Wednesday is the most expensive day to book, with an average nightly rate of £186

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

The most affordable month to stay in Chestertown is November, where the average nightly rate is £70 with an expected price drop of 46%. The most expensive month to stay in Chestertown is December, with an average nightly cost of £195 and a 52% increase in prices.

How far in advance should I book a hotel in Chestertown?

For the best deal, book a hotel in Chestertown 1 month in advance, with the lowest price found 22 days ahead at £52/night. Prices are higher on average 67 days in advance at £225/night.

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?

Hotels in Chestertown, MD show a range of prices for their rooms. These are determined by factors such as availability, locale and amenities. On average, rooms will be around £86 per night.

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

November is the cheapest month to book a hotel in Chestertown, MD. Prices can be 46% lower than other, busier months, so this is a great time to get a good deal.

Which day is cheapest to stay in Chestertown, MD?

Saturday is the day where you will typically find the lowest price for your hotel room in Chestertown, MD. The highest price tends to be on Tuesday.

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

The average temperature in Chestertown during August is around 24 °C which makes it the perfect time to spend time having fun and seeing something new outside at popular area attractions.

How many operators does momondo search for hotels in Chestertown?

As of August 2026, there are 47 operators available to choose from for hotels in Chestertown.

When did momondo last update prices for hotels in Chestertown?

Prices for hotels in Chestertown are refreshed on a daily basis.

Why use momondo?

Why should I book accommodation in Chestertown through momondo?

By quickly finding and returning Chestertown hotels and accommodation options, momondo can save you time and money. We search for hotels and accommodation deals from numerous independent and larger businesses. All you have to do is choose where you want to stay.

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

momondo finds you a great place to stay in Chestertown by enabling you to filter and refine your search. You can filter by price, location, amenities, review score and so much more.