Chester Holiday Packages

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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$324 per night from 27 May to 28 May
NZ$324
includes taxes & fees
27 May - 28 May
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 ...
"Our family has been coming to Annapolis for several generations. This trip may have been the best I can remember."

Reviewed on 30 Apr. 2025

Graduate 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
The price is NZ$384 per night from 4 May to 5 May
NZ$384
includes taxes & fees
4 May - 5 May
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 ...
"We had an undesirable use of the shower. It was extremely small and without a reomoveable showerhead therefore making it impossible to bathe and rinse. At the least if there was a removeable wand/shower handle it would allow for a short person to have the spray hit more than just the top of their ..."

Reviewed on 29 Apr. 2025

Historic Inns of Annapolis
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

3 out of 5
2600 Housley Road, Annapolis, MD
Fully refundable
The price is NZ$187 per night from 8 May to 9 May
NZ$187
includes taxes & fees
8 May - 9 May
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
"Wonderful staff!"

Reviewed on 29 Apr. 2025

Country Inn & Suites by Radisson, Annapolis, MD
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