Chester Holiday Packages

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Book your Chester holiday

Wotif is here to help you save your hard-earned cash.

Roll your flights and hotels into one easy package deal.

With your extra funds, you won't run out of things to do in Chester.

You could gain savings of up to . Also, with more than 550 airlines and 665,000 worldwide properties, it's easy to craft your perfect holiday.

With Wotif's competitive prices, you'll be zipping up your suitcase and hitting the skies before you know it.

Chester Accommodation

You're out of luck if you were hoping to secure accommodation in Chester. However, there are 6 properties just a quick car trip away. Have a squiz at your choices on Wotif.

Can't decide on where to get your shut-eye? Then let us help. The Waterfront Historic Kent Manor Inn (500 Kent Manor Dr) and The Inn at Chesapeake Bay Beach Club (180 Pier One Road) are some decent places not too far away.

Car Hire in Chester

Collecting a vehicle directly from Baltimore Washington International Thurgood Marshall Airport means that you don't need to bother with public buses or taxis. Hertz is just a quick walk from the luggage carousel.

Eager to hire a car in the centre of town? Enterprise (1418 Main St) is the closest rental company available. It's only 3 kilometres away.

Holidays to Chester

Counting down the days until you can kick back and chill out in Chester? We hear ya. Get there faster, or at least a bit more clued in, by reading up on this thrilling destination.

Chester is a neighbourhood in the Maryland state capital of Annapolis. You can find it 19 kilometres east of the centre of the city.

Want to learn how many people reside in Annapolis? At last count, it was around 38 000.

Top Chester hotels

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is NZ$309 per night from 10 Nov to 11 Nov
NZ$309
10 Nov - 11 Nov
includes taxes & fees
Stay at this 4-star business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and ...
"Cute decor"

Reviewed on 14 Oct 2025

Opens in a new windowGraduate by Hilton Annapolis
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
Book a stay at this historic hotel in Annapolis. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
"Staff is always very friendly and efficient. Great location, valet is convenient. Only downsides were the bed mattress (big sag) and cold temperature in room. Heat might not have been turned on yet"

Reviewed on 18 Oct 2025

Opens in a new windowHistoric Inns of Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd, Annapolis, MD
Fully refundable
The price is NZ$199 per night from 2 Nov to 3 Nov
NZ$199
2 Nov - 3 Nov
includes taxes & fees
Stay at this 3.5-star business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
"The room was very clean but the mattress not so great. I found hair on the sheets"

Reviewed on 15 Oct 2025

Opens in a new windowCrowne Plaza Annapolis by IHG
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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.