Chestertown Holiday Packages

Save when you book Chestertown package deals

Choose two or more items and save on your trip:

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$190 per night from 4 May to 5 May
AU$190
includes taxes & fees
4 May - 5 May
Comfort Inn & Suites Chestertown: Pet-friendly hotel with free breakfast and free WiFi. Located in the historical district.
"The room was nice and clean and the bathroom was recently updated. I was not able to connect my Roku to their WIFI however."

Reviewed on 22 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$208 per night from 29 Apr to 30 Apr
AU$208
includes taxes & fees
29 Apr - 30 Apr
The Lodge at Great Oak Landing: Golf lodge with free WiFi and free parking. Located on the waterfront.
"Wonderful quiet place. Enjoyed our night."

Reviewed on 27 Apr. 2025

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 4 May to 5 May
AU$119
includes taxes & fees
4 May - 5 May
Red Roof Inn & Suites Chestertown: Pet-friendly hotel with free WiFi and free parking. Located in the city centre.
"Easy to get to, food all around!"

Reviewed on 20 Apr. 2025

Red Roof Inn & Suites Chestertown
Don't see what you're looking for?
See all available properties in Chestertown
View all properties
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.