Chestertown Holiday Packages

Save when you book Chestertown package deals

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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

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock

Chestertown
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock : Pet-friendly holiday home with free WiFi and an outdoor pool. Located on the ...
Great vacation
"Great!"

Reviewed on 6 Sep. 2024

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
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$185 per night from 2 Jan to 3 Jan
AU$185
includes taxes & fees
2 Jan - 3 Jan 2025
Comfort Inn & Suites Chestertown: Pet-friendly hotel with free breakfast and free WiFi. Located in the business district.
Nice hotel
"Front desk staff was welcoming and friendly. We had a suite so I am guessing it was a bit larger than a regular room but it was really wonderful to have the extra space. The room was clean and the breakfast was decent (the coffee was good for hotel coffee). Would certainly stay here again when I ..."

Reviewed on 13 Dec. 2024

Comfort Inn & Suites Chestertown
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$122 per night from 2 Jan to 3 Jan
AU$122
includes taxes & fees
2 Jan - 3 Jan 2025
Red Roof Inn & Suites Chestertown: Pet-friendly hotel with free WiFi and free parking. Located in the historical district.
Nice but no breakfast
"Comfortable room and fair price for the room size. Very clean. Bathroom was nice but had a broken wall mounted hair dryer and the bathroom door did not latch closed so it stayed open about an inch. Front desk was businesslike but not the least bit friendly. There is no breakfast or even coffee offered. ..."

Reviewed on 10 Nov. 2024

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.