Chester Vacations from SAR4,142

Book a Hotel + Flight together to unlock savings

Photo by Patricia Knorr

  • Plan, book, travel with confidence

  • Better together

    Save up to SARĀ 5,400 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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    Plan, book, and manage your trip all in one place

The Latest Chester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Price was SAR4,880, price is now SAR4,142 per person
SAR4,142
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Dammam (DMM) to Baltimore (BWI)
8.2/10 Very Good! (1,005 reviews)
Overall it was a good stay the room was clean.The staff was good in the beginning but at checkout the women working the front desk was rude and acted as if she didnā€™t want to be ask questions about the shuttles. And there was a problem with the printer I assume because I never received my receipt and she said she would email it .

Reviewed on 13 July 2026

Phoenix Park Hotel

Phoenix Park Hotel

3.5 out of 5
Northwest
Price was SAR5,727, price is now SAR4,823 per person
SAR4,823
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Dammam (DMM) to Baltimore (BWI)
9.4/10 Exceptional! (2,206 reviews)

The Poppy Georgetown

The Poppy Georgetown

4 out of 5
Northwest
Price was SAR6,379, price is now SAR5,465 per person
SAR5,465
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Dammam (DMM) to Baltimore (BWI)
9.4/10 Exceptional! (587 reviews)

The River Inn

The River Inn

4 out of 5
Northwest
Price was SAR5,350, price is now SAR4,677 per person
SAR4,677
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Dammam (DMM) to Baltimore (BWI)
9.4/10 Exceptional! (2,011 reviews)

The Churchill Hotel near Embassy Row

The Churchill Hotel near Embassy Row

4 out of 5
Northwest
Price was SAR5,658, price is now SAR5,038 per person
SAR5,038
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Dammam (DMM) to Baltimore (BWI)
8.8/10 Excellent! (1,006 reviews)
Y

Reviewed on 16 July 2026

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 SARĀ 421 per night from Jul 26 to Jul 27
SARĀ 421
SARĀ 609 total
26 Jul - 27 Jul
includes taxes & fees
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 SARĀ 446 per night from Jul 26 to Jul 27
SARĀ 446
SARĀ 508 total
26 Jul - 27 Jul
includes taxes & fees
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 SARĀ 445 per night from Aug 16 to Aug 17
SARĀ 445
SARĀ 507 total
16 Aug - 17 Aug
includes taxes & fees
Crowne Plaza Annapolis by IHG
See all 1,185 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 from SAR4,142 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.