Chester Vacations from ￥187,602

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The Latest Chester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Washington DC Dupont Circle

The Royal Sonesta Washington DC Dupont Circle

4.5 out of 5
Northwest
per person
Aug 21 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Washington (DCA)
8.6/10 Excellent! (1,178 reviews)
AC was not cool enough and doors to bedroom and bathroom do not close for privacy.

Reviewed on Jun 20, 2025

Hotel Madera

Hotel Madera

4 out of 5
Downtown Washington D.C.
per person
Aug 21 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Washington (DCA)
9.2/10 Wonderful! (1,005 reviews)
Check in was super fast. Front desk super helpful & nice. However housekeeping tree away my son’s brand new $250 debtal retainer. Kinda ruined the day

Reviewed on Jun 19, 2025

The Churchill Hotel near Embassy Row

The Churchill Hotel near Embassy Row

4 out of 5
Northwest
per person
Aug 21 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Washington (DCA)
8.8/10 Excellent! (1,767 reviews)
Wonderful experience

Reviewed on Jun 19, 2025

Canopy by Hilton Washington Embassy Row

Canopy by Hilton Washington Embassy Row

4 out of 5
Downtown Washington D.C.
per person
Aug 21 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Washington (DCA)
9.2/10 Wonderful! (541 reviews)
Great convenient modern hotel. Corner room is the best.

Reviewed on Jun 16, 2025

The Henley Park Hotel

The Henley Park Hotel

4 out of 5
Downtown Washington D.C.
per person
Aug 21 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Washington (DCA)
9/10 Wonderful! (1,078 reviews)
Wonderfully situated, convenient, close to all the important things to see and do. Friendly staff willing to go the extra mile to help. My room was at 59 degrees and although I tried to change the temp it was either that or turning the ac off. I asked for help and they couldn’t fix it. That’s too cold, even for me!

Reviewed on Jun 19, 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! (1,789 reviews)
"Wonderful experience at a beautiful, historic hotel. Great location!"

Reviewed on Jun 16, 2025

Get rates
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
The price is ￥15,713 per night from Jul 21 to Jul 22
￥15,713
￥17,913 total
Jul 21 - Jul 22
includes taxes & fees
8.4/10 Very Good! (1,007 reviews)
"Conveniently located and clean. Great prices"

Reviewed on Jun 19, 2025

Hilton Garden Inn Annapolis Downtown
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 ￥14,716 per night from Jul 2 to Jul 3
￥14,716
￥16,777 total
Jul 2 - Jul 3
includes taxes & fees
9/10 Wonderful! (1,003 reviews)
"Great room, parking, and breakfast"

Reviewed on Jun 20, 2025

Country Inn & Suites by Radisson, Annapolis, MD
See all 1,239 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 ￥187,602 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.