Chester Holidays

Photo by Patricia Knorr

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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 S$177 per night from 2 Aug to 3 Aug
S$177
2 Aug - 3 Aug
includes taxes & fees
9/10 Wonderful! (1,903 reviews)
"Great staff"

Reviewed on 13 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 S$159 per night from 19 Jul to 20 Jul
S$159
19 Jul - 20 Jul
includes taxes & fees
8.6/10 Excellent! (1,039 reviews)
"Loved having a shuttle driver and having a full service restaurant on site."

Reviewed on 13 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 S$175 per night from 9 Aug to 10 Aug
S$175
9 Aug - 10 Aug
includes taxes & fees
8.8/10 Excellent! (1,022 reviews)
"This hotel is in a convenient place, with several restaurants within walking distance and a mall just across the street. The front desk staff was helpful and polite. The hotel was not very clean. The carpets in the lobby and common areas appear dirty and stained. In the pool area, no clean towels ..."

Reviewed on 13 Jul, 2026

Crowne Plaza Annapolis by IHG
See all 1,189 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

St. Michaels: 2-Hour Relaxing Chesapeake Sail on Epiphany

St. Michaels: 2-Hour Relaxing Chesapeake Sail on Epiphany

S$343
per adult
St. Michaels: 2-Hour Relaxing Chesapeake Sail on Epiphany
Picture 6 for Activity St. Michaels: 2-Hour Wine Tasting on Sailing Cruise Epiphany

St. Michaels: 2-Hour Wine Tasting on Sailing Cruise Epiphany

S$378
per adult
St. Michaels: 2-Hour Wine Tasting on Sailing Cruise Epiphany
St Michaels: 2-Hour Chesapeake Bay Sail on Lady Patty

St Michaels: 2-Hour Chesapeake Bay Sail on Lady Patty

S$202
per adult
St Michaels: 2-Hour Chesapeake Bay 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.