
Chester Holidays from AU$3,506
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to AU$703 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Your Chester Holiday
When a city getaway is calling, answer it with a holiday package to Chester. The neighbourhood of Kent Narrows, which is good for cycling, views and nature, makes a great base for your adventures. You'll want to do a little exploring during your trip to Chester. Drop by popular attractions like Chesapeake Bay Environmental Centre, Eastern Neck National Wildlife Refuge and Matapeake State Park. Check out Expedia's extensive range of travel options and start planning your perfect holiday to Chester today.
The Latest Chester Holiday Deals
Price found within the past 48 hours. Click for updated prices.


Willard InterContinental Washington by IHG
Downtown Washington D.C.
per person
6 Jul - 11 Jul
found 1 day ago
Return direct flight included
Sydney (SYD) to Washington (DCA)
9.4/10 Exceptional! (1,003 reviews)
Such a wonderful stay. The property is very convenient to the national mall; all the monuments and Smithsonian museums are within walking distance. The room was spacious with comfortable beds. The service was impeccable. We look forward to staying again.
Reviewed on 28 Apr. 2025

Salamander Washington DC
Southwest
per person
6 Jul - 11 Jul
found 1 day ago
Return direct flight included
Sydney (SYD) to Washington (DCA)
9.4/10 Exceptional! (1,003 reviews)
My wife and i were celebrating our honeymoon. Tired and exhauted due to lengthy drive we finally arrived. Nate the bell man greeted us with an immediate smile and warm welcome. He took our lugguage to our room. Austin at the front desk was extremely helpful and very acvomidating to our room. Very professional and yet personally a true star player to the hotel. The hotel is gery close to Nationa mall so easy and walkable. The room very well appointed to every detailed and extremely clean plenty of space. Lastly but not least Christian the FOB manager was incredible, he was personally and very kind, gave me great dinner options to the hotel and surrounding area. He also gave my wife and i a toasting to champaigne to ring in our marriage. Tobi the Director of FD very kind and personal we spoke and shared in stories as I was a former AGM to Hilton. KIond blesssing to such an incredible staff we will be back for sure!
Reviewed on 30 Apr. 2025

Sofitel Washington DC Lafayette Square
Downtown Washington D.C.
per person
6 Jul - 11 Jul
found 1 day ago
Return direct flight included
Sydney (SYD) to Washington (DCA)
9/10 Wonderful! (1,008 reviews)
Large water bug/cockroach in our shower. Staff was responsive and removed it. Worst shower pressure EVER!! Felt like I was not clean after the shower. I will not be returning.
Reviewed on 27 Apr. 2025

Global Luxury Suites at Capitol Hill
Northeast
per person
6 Jul - 11 Jul
found 1 day ago
Return direct flight included
Sydney (SYD) to Washington (DCA)
7.8/10 Good! (510 reviews)
Need instructions on where trash shute is located. And locating the actual property of building wasn't the easiest to find. Need numbers on building that can be seen easily. Otherwise it was a perfect location.
Reviewed on 29 Apr. 2025
Chester Holiday
Chester Essential Information
Language | English |
---|---|
Currency | U.S dollars |
Closest Airport | Baltimore Washington Intl. Thurgood Marshall Airport (BWI) |
Population | 4,200 |
Max Temp Winter | 7ºC |
Max Temp Summer | 27ºC |
Top Sights | Sandy Point State Park, Sandy Point Beach and Matapeake State Park |
Our pick of the best Chester Hotel Deals

Historic Inns of Annapolis
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is AU$340 per night from 8 May to 9 May
AU$340
includes taxes & fees
8 May - 9 May
8.8/10 Excellent! (1,761 reviews)
"Water pressure has to be fixed!"
Reviewed on 29 Apr. 2025

Country Inn & Suites by Radisson, Annapolis, MD
2600 Housley Road, Annapolis, MD
Fully refundable
The price is AU$181 per night from 7 May to 8 May
AU$181
includes taxes & fees
7 May - 8 May
8.8/10 Excellent! (1,002 reviews)
"Wonderful staff!"
Reviewed on 29 Apr. 2025

The Westin Annapolis
100 Westgate Cir, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is AU$265 per night from 4 May to 5 May
AU$265
includes taxes & fees
4 May - 5 May
8.6/10 Excellent! (1,000 reviews)
"Hotel was under renovation so things were covered in plastic, etc. but overall very nice."
Reviewed on 23 Apr. 2025
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.
More holiday ideas
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.