Chester Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Patricia Knorr

Top hotels in Chester

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 2.370.396 ₫ per night from 20 Jul to 21 Jul
2.370.396 ₫
3.601.369 ₫ total
20 Jul - 21 Jul
includes taxes & fees
9/10 Wonderful! (1,867 reviews)
"Staff was friendly, helpful and wonderful. Room was good, location is great."

Reviewed on 3 Jul 2026

Historic Inns of Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
The price is 2.503.474 ₫ per night from 5 Jul to 6 Jul
2.503.474 ₫
2.853.960 ₫ total
5 Jul - 6 Jul
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
"The room is clean. Spacious and quiet. Bed is comfortable. We will stay here again."

Reviewed on 3 Jul 2026

DoubleTree by Hilton Hotel Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
Fully refundable
The price is 2.997.858 ₫ per night from 12 Jul to 13 Jul
2.997.858 ₫
3.417.558 ₫ total
12 Jul - 13 Jul
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"Excelent"

Reviewed on 2 Jul 2026

Crowne Plaza Annapolis by IHG
See all 1,190 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.

Stay near popular Chester attractions

Chesapeake Exploration Center

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

Frequently asked questions

How much does a Chester holiday package cost?
Offering great value package deals 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.

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