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 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 Sunset Bayview: sleeps 6

Waterfront Sunset Bayview: sleeps 6

Chester MD
Waterfront Sunset Bayview: sleeps 6: Holiday home with free WiFi and parking. Located on the waterfront.
"Very nice host and beautiful modern house! Close to town and had a dock right there to sit out on and enjoy a cup or coffee! Only complaint was one shower never got hot or warm but we just used one and it was fine"

Reviewed on 22 May 2026

Opens in a new windowWaterfront Sunset Bayview: sleeps 6
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 MD
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 ...
"Beautiful, peaceful and comfortable. There’s plenty of space to gather and enjoy each other’s company both inside and out. We loved watching the river from the shade of trees, from the dock, from the screened porch and from inside the house. Loved our stay!"

Reviewed on 8 June 2026

Opens in a new windowWaterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
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 AU$218 per night from 16 June to 17 June
AU$218
16 June - 17 June
includes taxes & fees
Historic Inns of Annapolis: Pet-friendly hotel with free WiFi and a bar/lounge. Located in the historical district.
"Excellent location, walking distance to everything we had plans on seeing"

Reviewed on 9 June 2026

Opens in a new windowHistoric 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.