Chestertown Holiday Packages

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Book your Chestertown holiday

If you want to save some big bucks, Wotif is your new best mate.

What's the secret, you may wonder? Easy, we can roll your hotels and flights into one affordable little package.

Chestertown is waiting for you!

Many travellers see savings of as much as . Also, you'll be able to mix and match from more than 550 partner airlines and 665,000 properties.

Some of the most competitive prices under the sun are on Wotif. So request that annual leave, pull out your passport and hit the clouds!

Chestertown Accommodation

There's no time to dilly-dally when it comes to booking a place to stay. With just 4 accommodations in Chestertown, you'd best grab one of Wotif's great deals before they're all gone.

Busy buying plane tickets for your upcoming getaway? Don't have time to scan the net for hours for somewhere to get your beauty sleep? Why not go with one of our top suggestions? The John L Stam House and Holiday Inn Express Hotel & Suites Chestertown are some of the most well-known properties in the area.

Car Hire in Chestertown

Landing at Baltimore Washington International Thurgood Marshall Airport? Pick up your keys at Hertz and get your holiday rolling without delay.

Enterprise (121 Flatland Rd) is in the centre of the city and is a great place to get your ride. Browse their selection and dash off on your next adventure.

Holidays to Chestertown

Locked in that window seat, packed your fanciest thongs but don't know all that much about Chestertown? Listen up. We can tell you a thing or two about this wonderful destination.

Want to visualise where you'll be spending your nights? Chestertown is located 45 kilometres east of the popular city of Baltimore.

With so many amazing things to do in the area, it's not difficult to see why some 5 000 people call this area of Eastern Shore home.

Top Chestertown hotels

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is AU$181 per night from 27 Apr to 28 Apr
AU$181
includes taxes & fees
27 Apr - 28 Apr
Comfort Inn & Suites Chestertown: Pet-friendly hotel with free breakfast and free WiFi. Located in the historical district.
"Inside the building it was clean, quiet and nice. In the back parking lot, it was very dirty. The grounds surrounding the lot was littered with trash and debris. One person looked to be sleeping in his car. I did appreciate the very bright lighting in that lot. A small clean up of the back lot would ..."

Reviewed on 12 Apr. 2025

Comfort Inn & Suites Chestertown
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3.5 out of 5
22170 Great Oak Landing Rd, Chestertown, MD
Fully refundable
The price is AU$209 per night from 21 Apr to 22 Apr
AU$209
includes taxes & fees
21 Apr - 22 Apr
The Lodge at Great Oak Landing: Golf lodge with free WiFi and free parking. Located on the waterfront.
Respite
"Generally okay, Clean but property could use some upgrade"

Reviewed on 27 Oct. 2024

The Lodge at Great Oak Landing
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2 out of 5
160 Scheeler Rd, Chestertown, MD
Fully refundableReserve now, pay when you stay
The price is AU$119 per night from 27 Apr to 28 Apr
AU$119
includes taxes & fees
27 Apr - 28 Apr
Red Roof Inn & Suites Chestertown: Pet-friendly hotel with free WiFi and free parking. Located in the city centre.
"I stayed here one night and got a stripper pregnant. 10/10 will book again."

Reviewed on 4 Apr. 2025

Red Roof Inn & Suites Chestertown
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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.