Chester Vacations from ￥187,615

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The Latest Chester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Club Quarters Hotel in Washington DC

Club Quarters Hotel in Washington DC

3 out of 5
Downtown Washington D.C.
per person
Sep 15 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Washington (DCA)
8.8/10 Excellent! (1,607 reviews)
Room is basic but good enough for a short stay if you’re not staying in much. Location is convenient. Service from the staff is lacking. Overall, really good value for the price.

Reviewed on Aug 6, 2025

SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
per person
Oct 27 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Washington (DCA)
9.8/10 Exceptional! (25 reviews)
Absolutely incredible hotel that we happened upon on a whim. Brand new, absolutely stunning and Johnny the concierge made our night and had us feeling right at home despite the grandeur of the establishment. Can’t recommend this place enough and shout out to Johnny ❤️

Reviewed on Aug 3, 2025

The St. Gregory Hotel

The St. Gregory Hotel

4 out of 5
Downtown Washington D.C.
per person
Oct 27 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Washington (DCA)
8.6/10 Excellent! (1,004 reviews)
My stay was very pleasant

Reviewed on Jul 27, 2025

The Jefferson, Washington, DC

The Jefferson, Washington, DC

5 out of 5
Downtown Washington D.C.
per person
Oct 27 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Washington (DCA)
9.8/10 Exceptional! (961 reviews)
Very well trained staff and clean rooms. They earned their high ratings

Reviewed on Jul 30, 2025

Salamander Washington DC

Salamander Washington DC

5 out of 5
Southwest
per person
Oct 27 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Washington (DCA)
9.4/10 Exceptional! (1,001 reviews)
The property staff were incredibly accommodating friendly and helpful. The only issue was the waitresses were non existent anytime you needed a drink or for someone to take your order.

Reviewed on Aug 3, 2025

Find the Best Chester Vacation Packages

Chester Hotel Deals

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! (1,824 reviews)
"We’ve been here a few times and continue to to love the location, staff and comfortable beds."

Reviewed on Aug 4, 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 ￥22,816 per night from Aug 17 to Aug 18
￥22,816
￥26,011 total
Aug 17 - Aug 18
includes taxes & fees
9.4/10 Exceptional! (1,005 reviews)
"We had a wonderful stay at THE GRADUATE. We will definitely return when we visit Annapolis."

Reviewed on Aug 6, 2025

Graduate by Hilton Annapolis
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
The price is ￥14,266 per night from Aug 13 to Aug 14
￥14,266
￥16,263 total
Aug 13 - Aug 14
includes taxes & fees
9/10 Wonderful! (1,009 reviews)
"Property grounds was very good and had a lot of amenities nearby. Staff was very nice and accommodating. The pool on property was amazing."

Reviewed on Aug 4, 2025

Country Inn & Suites by Radisson, Annapolis, MD
See all 1,246 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.

Frequently asked questions

How much does a Chester vacation package cost?
Offering great value package deals from ￥187,615 on Expedia, you'll be thrilled with how little a vacation 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 vacation 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 vacation. 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 vacation as a package?
Expedia vacation 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 customized Chester vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Chester?
If you're considering a spur-of-the-moment Chester vacation, 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 vacation 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.