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

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 AU$236 per night from 23 Feb to 24 Feb
AU$236
includes taxes & fees
23 Feb - 24 Feb
Graduate by Hilton Annapolis: Pet-friendly hotel with free WiFi and a bar/lounge. Located in the city centre.
"Dog friendly"

Reviewed on 20 Jan. 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 AU$281 per night from 9 Feb to 10 Feb
AU$281
includes taxes & fees
9 Feb - 10 Feb
Historic Inns of Annapolis: Pet-friendly hotel with free WiFi and a bar/lounge. Located in a shopping district.
Comfortable historic hotel
"The room was spacious and the lights and heater were on, so it was very inviting when we walked in. The bed was comfortable. The hotel itself has the historic feel we enjoy when we stay in Annapolis. The front desk clerk and valet drivers were all gracious and professional. My husband and I had an ..."

Reviewed on 28 Jan. 2025

Historic Inns of Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is AU$185 per night from 9 Feb to 10 Feb
AU$185
includes taxes & fees
9 Feb - 10 Feb
DoubleTree by Hilton Hotel Annapolis: Pet-friendly hotel with free WiFi and free parking. Located in a regional park.
Great Hotel
"Came for the Military Bowl. Rooms were comfortable and very quite. Staff was excellent and having a shuttle to and from the football stadium was an added plus. Centrally located."

Reviewed on 23 Jan. 2025

DoubleTree by Hilton Hotel 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.