Chester Holidays from AU$2,408

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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.
The St. Gregory Hotel

The St. Gregory Hotel

4 out of 5
Downtown Washington D.C.
Price was AU$3,723, price is now AU$2,408 per person
AU$2,408
per person
21 Sept - 28 Sept
found 12 hours ago
Return direct flight included
Melbourne (MEL) to Washington (WAS)
8.6/10 Excellent! (1,005 reviews)
Good location, friendly staff, great breakfast, clean and quiet rooms, best sleep in a week

Reviewed on 12 Aug. 2025

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Price was AU$4,219, price is now AU$2,727 per person
AU$2,727
per person
21 Sept - 28 Sept
found 12 hours ago
Return direct flight included
Melbourne (MEL) to Washington (WAS)
9/10 Wonderful! (1,009 reviews)
Everything was great

Reviewed on 15 Aug. 2025

SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
Price was AU$4,057, price is now AU$2,710 per person
AU$2,710
per person
21 Sept - 28 Sept
found 12 hours ago
Return direct flight included
Melbourne (MEL) to Washington (WAS)
9.8/10 Exceptional! (39 reviews)
Accommodating staff,professional,pleasant. Clean,I’d stay again!

Reviewed on 20 Aug. 2025

Hampton Inn & Suites Washington DC-Navy Yard

Hampton Inn & Suites Washington DC-Navy Yard

3 out of 5
Navy Yard
Price was AU$3,434, price is now AU$2,547 per person
AU$2,547
per person
21 Sept - 28 Sept
found 12 hours ago
Return direct flight included
Melbourne (MEL) to Washington (WAS)
8.8/10 Excellent! (1,002 reviews)
Stay was very good.

Reviewed on 20 Aug. 2025

Arlo Washington DC

Arlo Washington DC

4 out of 5
Northwest
Price was AU$3,310, price is now AU$2,483 per person
AU$2,483
per person
21 Sept - 28 Sept
found 12 hours ago
Return direct flight included
Melbourne (MEL) to Washington (WAS)
9.2/10 Wonderful! (836 reviews)
The vibes was nice amd its kinda tucked away but still easy navigate around the city.

Reviewed on 17 Aug. 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

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
9.8/10 Exceptional! (92 reviews)
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

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Waterfront 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
8.8/10 Excellent! (1,836 reviews)
"There were no ghosts!"

Reviewed on 20 Aug. 2025

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Historic Inns of Annapolis
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$285 per night from 2 Sept to 3 Sept
AU$285
2 Sept - 3 Sept
includes taxes & fees
9.2/10 Wonderful! (1,009 reviews)
Cool place, comfy bed!!!
"Cool place, cool vibe! Loved all the pictures and the strong decor. Front desk check in and out was quick & efficient. The parking valets were quick and very friendly. Walking distance to shopping, restaurants and bars! The bed was super comfy! We would definitely stay here again!"

Reviewed on 20 Aug. 2025

Graduate by Hilton Annapolis
See all 1,248 properties in Chester
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.
All Inclusive Holidays
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Cheap Holidays
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beach holidays
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Beach Holidays

Frequently asked questions

How much does a Chester holiday package cost?
Offering great value package deals from AU$2,408 on Expedia, you'll be thrilled with how little a holiday to Chester costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Chester?
The off-season is the best time to visit Chester if you're trying to save. Another tip for getting cheap Chester holiday packages? Try to avoid visiting during public holidays and any major events or festivals.
How many days is enough for Chester?
Generally, a handful of days is enough to explore the major attractions during your Chester holiday. But if you prefer to have time to chill out or take day trips, consider extending your itinerary.
How to find the best Chester package deals?
Start your search for a Chester package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply some filters, like "Property type" and "Guest rating," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Chester package deal straight away, simply switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Chester escape off to a flying start.
Is it cheaper to book a Chester holiday as a package?
Expedia holiday packages are designed to make your money go further. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component individually. And you'll still enjoy the freedom to create a customised Chester holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday package to Chester?
If you're considering a spur-of-the-moment Chester holiday, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can find awesome deals on your flights and hotels by booking well in advance.
How to plan a trip to Chester?

  1. Choose the best time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to travel to Chester.
  2. Budget wisely: On top of the cost of your stay, you should consider other expenses too. These include food, flights and transportation. Also, put aside some extra funds for unexpected costs that may arise during your trip to Chester.
  3. Work out your trip length: Think about how much time you'd like to spend discovering Chester. Plan your days so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to find a Chester holiday package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.