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

Sagamore Pendry Baltimore

Sagamore Pendry Baltimore

5 out of 5
1715 Thames St., Baltimore, MD
Fully refundableReserve now, pay when you stay
The price is AU$663 per night from 20 Feb to 21 Feb
AU$663
includes taxes & fees
20 Feb - 21 Feb
Sagamore Pendry Baltimore: Luxury hotel with free WiFi and outdoor pool. Located in the entertainment district.
"Our go-to hotel for the staff, amenities, and location!"

Reviewed on 19 Jan. 2025

Sagamore Pendry Baltimore
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$186 per night from 9 Feb to 10 Feb
AU$186
includes taxes & fees
9 Feb - 10 Feb
Comfort Inn & Suites Chestertown: Pet-friendly hotel with free breakfast and free WiFi. Located in the business district.
"Friendly atmosphere and well stocked breakfast bar! Comfortable clean room!"

Reviewed on 12 Jan. 2025

Comfort Inn & Suites Chestertown
Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A

2.5 out of 5
2112a Emmorton Park Road, Edgewood, MD
Fully refundableReserve now, pay when you stay
The price is AU$98 per night from 3 Feb to 4 Feb
AU$98
includes taxes & fees
3 Feb - 4 Feb
Quality Inn & Suites Bel Air I-95 Exit 77A: Business-friendly hotel with free breakfast and free WiFi. Guests love the helpful staff!
Nice hotel
"It was amazing"

Reviewed on 28 Jan. 2025

Quality Inn & Suites Bel Air I-95 Exit 77A
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.