Chester Holidays

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Chester Holiday

Our pick of the best 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 NZ$241 per night from 29 July to 30 July
NZ$241
29 July - 30 July
includes taxes & fees
9/10 Wonderful! (1,866 reviews)
"The staff was very friendly. The room was clean."

Reviewed on 2 July 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 NZ$191 per night from 5 July to 6 July
NZ$191
5 July - 6 July
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
"Check in was smooth, typical. Room was located on a wing away from the lobby which we liked b/c we could access directly from the parking lot. We were in and out a lot during our stay so that was nice. Room was clean with your usual amenities nothing outstanding. Bathroom again fairly clean but the ..."

Reviewed on 1 July 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 NZ$229 per night from 12 July to 13 July
NZ$229
12 July - 13 July
includes taxes & fees
8.8/10 Excellent! (1,009 reviews)
"Never stayed at a Crowne Plaza before, I was thoroughly impressed!"

Reviewed on 2 July 2026

Crowne Plaza Annapolis by IHG
See all 1,188 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

What to do in Chester

Epiphany

2 Hour Chesapeake Day Sail on Catamaran Epiphany

NZ$417
per adult
2 Hour Chesapeake Day Sail on Catamaran Epiphany
2-Hour Relaxing Chesapeake Day Sail on Lady Patty

2-Hour Relaxing Chesapeake Day Sail on Lady Patty

NZ$272
per adult
2-Hour Relaxing Chesapeake Day Sail on Lady Patty
See all activities in Chester

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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.