Chester Vacations

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    Save up to SAR 390 when you book a flight and hotel together*
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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 SAR 634 per night from Apr 21 to Apr 22
SAR 634
SAR 851 total
includes taxes & fees
21 Apr - 22 Apr
8.8/10 Excellent! (1,736 reviews)
"Attentive! Clean, well decorated. Perfect location"

Reviewed on 15 April 2025

Historic Inns of 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 SAR 348 per night from May 1 to May 2
SAR 348
SAR 396 total
includes taxes & fees
1 May - 2 May
8.8/10 Excellent! (1,002 reviews)
"Seemed safe and the room was quiet. Easy parking right in front. Shower was good, clean and comfy. Nice grill pub ‘Lures’ just down the street."

Reviewed on 16 April 2025

Country Inn & Suites by Radisson, Annapolis, MD
The Westin Annapolis
The Westin Annapolis
4 out of 5
100 Westgate Cir, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is SAR 559 per night from Apr 22 to Apr 23
SAR 559
SAR 637 total
includes taxes & fees
22 Apr - 23 Apr
8.6/10 Excellent! (982 reviews)
"Stayed here for a wedding, but it was our first time to the area. Hotel is great, clean friendly. But the real value was the location. Walking distance to restaurants, convenience, stores, and bars. It was an eight minute walk to a super cute coffee shop, bakery. Parking seemed unnecessarily expensive, ..."

Reviewed on 7 April 2025

The Westin Annapolis
See all 1,199 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 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.

Discover the most popular places to visit in Chester

Chesapeake Exploration Center

Learn about the events happening at Chesapeake Exploration Center during your trip to Kent Narrows. Stroll along the area's marina or simply enjoy its seafood restaurants.

Chesapeake Exploration Center