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 accommodations 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

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Chester
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!: Family-friendly holiday home with free WiFi and parking. Located on the ...
Great location for a relaxing, fun, family vacation
"Our family (ages 16 - 73) enjoyed our week here very much. Harry and Scott were great to work with and were always available to answer questions. We were aiming for a relaxing, low key week so we didn't stray too far from the house for adventures, but that just goes to show we had everything we needed ..."

Reviewed on 8 Aug. 2025

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St, Annapolis, MD
The price is AU$282 per night from 3 Sept to 4 Sept
AU$282
3 Sept - 4 Sept
includes taxes & fees
Graduate by Hilton Annapolis: Pet-friendly hotel with free WiFi and a bar/lounge. Located in the historical district.
"Very good"

Reviewed on 20 Aug. 2025

Graduate by Hilton Annapolis
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle, Annapolis, MD
Historic Inns of Annapolis: Pet-friendly hotel with free WiFi and a bar/lounge. Located in the historical district.
Cozy and Convenient Stay
"Friendly and accommodating staff! Room was bright, comfortable, cozy, and clean! Nice amenities like a small fridge and single cup coffee maker in the room. Be careful stepping into the shower, as it's a little slippery. Perhaps some "non-skid" strips or a mat of some sort on the bottom of the tub. ..."

Reviewed on 26 Aug. 2025

Historic Inns of Annapolis
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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.