Chester Holiday Packages

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Top Chester holiday packages

Price found within the past 48 hours. Click for updated prices.
Hotel Arboretum
Sofitel Washington DC Lafayette Square
Omni Shoreham Hotel
Lyle Washington D.C.
The Watergate Hotel

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 NZ$293. 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

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
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 ...
"Great accommodations"

Reviewed on 20 Jun. 2025

Country Inn & Suites by Radisson, Annapolis, MD
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 ...
"We loved the area as well as the hotel. It's a 4 minute walk from the waterfront and has a great view of the state capital building. My only complaint would be that the A/C for my room stop functioning on my fourth night. We were moved to another room and the A/C in that room also didn't work. They ..."

Reviewed on 20 Jun. 2025

Historic Inns of Annapolis
Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

3 out of 5
174 West Street, Annapolis, MD
Fully refundableReserve now, pay when you stay
Stay at this 3-star business-friendly hotel in Annapolis. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful ...
"Conveniently located and clean. Great prices"

Reviewed on 19 Jun. 2025

Hilton Garden Inn Annapolis Downtown
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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.