Chester Vacations

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  • Plan, book, travel with confidence

  • Better together

    Save up to AED 5,000 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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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 AED 331 per night from Jul 6 to Jul 7
AED 331
AED 503 total
6 Jul - 7 Jul
includes taxes & fees
9/10 Wonderful! (1,877 reviews)
"I loved the building. It’s in a lovely spot a block from the bay so shops and restaurants are right out the front door. The building I stayed in was terrific. The only bummer, was my room was quite small, so I would advise not staying in room 1408. It was the smallest room I’ve ever stayed in. I ..."

Reviewed on 29 June 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 AED 350 per night from Jul 5 to Jul 6
AED 350
AED 399 total
5 Jul - 6 Jul
includes taxes & fees
8.6/10 Excellent! (1,019 reviews)
"Nice hotel with proximity to many restaurants and shopping. We were there for a quick stay and did not utilize the hotel’s amenities. We did not encounter any issues during our stay. Of note: the front desk staff made sure we got our famous DoubleTree Cookies (yummy) and the A/C in the room worked ..."

Reviewed on 29 June 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
The price is AED 419 per night from Jul 12 to Jul 13
AED 419
AED 477 total
12 Jul - 13 Jul
includes taxes & fees
8.8/10 Excellent! (1,008 reviews)
"It wasn’t the property or the room.. It was the unfriendly staff members. Not a single smile from the second we walked in… the front desk act as if we were bothering them.. never again"

Reviewed on 29 June 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 at 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 vacation package cost?
Offering excellent value package deals on Expedia, you'll be pleasantly surprised at how much a vacation to Chester costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Chester?
Travel in the off-peak season and you're likely to score cheap Chester vacation packages. Keep in mind that school vacation periods and local festivals and events can impact prices, so do a little research before you go.
How to find the best Chester package deals?
Use Expedia's handy filters to help you find some terrific Chester package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or search for Chester package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Chester vacation as a package?
You can enjoy significant savings on your Chester escape by booking a customized vacation package. Check the "Package" heading, then select your destination and travel dates to see the best flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Chester?
If you've got your Chester vacation dates locked in, book as soon as you can to bag some fantastic deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Chester?

  1. Choose your dates: What you plan to do in Chester and your favorite season will help you decide when to go.
  2. Plan your budget wisely: Besides the cost of your accommodations, you'll need to factor in other expenses too. These include transportation, food and flights. Also, put aside a little extra for unexpected expenses that could arise during your trip to Chester.
  3. Determine how many days away: Start by compiling a list of the sights and activities you'd like to experience in Chester. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to choose a Chester vacation package that brings all your bookings together.