Chester Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Patricia Knorr

  • Plan, book, travel with confidence

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    Better together

    Save up to ₩234,741 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

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
The price is ₩141,549 per night from Aug 25 to Aug 26
₩141,549
₩208,866 total
Aug 25 - Aug 26
includes taxes & fees
8.8/10 Excellent! (1,823 reviews)
"Lovely room. Comfortable bed."

Reviewed on Aug 13, 2025

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 ₩222,332 per night from Aug 24 to Aug 25
₩222,332
₩253,458 total
Aug 24 - Aug 25
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"Upscale hotel, great location, walkable"

Reviewed on Aug 15, 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 ₩134,582 per night from Aug 24 to Aug 25
₩134,582
₩153,423 total
Aug 24 - Aug 25
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
"New roof was being replaced. A bit messy and noisy around parking area. Room was OK. Staff was great and breakfast was good. Breakfast area lost air conditioning so this area was a bit uncomfortable."

Reviewed on Aug 13, 2025

Country Inn & Suites by Radisson, Annapolis, MD
See all 1,243 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 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.