Chester Vacations from $347

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Your Chester Vacation

Reserve a Chester vacation package and get set to experience the best of this city. Consider basing yourself in the neighborhood of Kent Narrows, which is good for cycling, views and nature. If your trip to Chester includes some sightseeing, check out renowned attractions like Chesapeake Bay Environmental Center, Eastern Neck National Wildlife Refuge and Love Point State Park. Stop daydreaming and start doing. Browse the multitude of options on Expedia today and finally put your Chester vacation plans into gear!

The Latest Chester vacation packages

Price found within the past 48 hours. Click for updated prices.
Phoenix Park Hotel

Phoenix Park Hotel

3.5 out of 5
Northwest
Save 100% on your flight
Price was $548, price is now $347 per person
$347
per person
Jul 31 - Aug 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.4/10 Exceptional! (2,199 reviews)
Room was small but nice. I didn’t need much. It’s a great location!

Reviewed on Jun 24, 2026

Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $969, price is now $535 per person
$535
per person
Sep 6 - Sep 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.8/10 Excellent! (1,016 reviews)
Property is clean but well overdue for updates. The room was old and dated. It had a broken bathroom vanity and our AC was barely working. AC required multiple resets to get it to blow cold air, it was extremely loud when it turned on, and required to be reset multiple times throughout our 3 nights there. When informed of the poorly working AC, staff offered very minimal solutions. No on was on site to fix the issue, no room change offered and no compensation offered. No follow up was done with us to ensure that the issue had been fixed after we informed them we were able to reset our AC ourselves. Would definitely not stay again.

Reviewed on Jun 18, 2026

Hotel AKA Washington Circle

Hotel AKA Washington Circle

4 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $1,002, price is now $619 per person
$619
per person
Sep 6 - Sep 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.2/10 Wonderful! (1,295 reviews)
Wonderful people, good location, spacious room.

Reviewed on Jun 24, 2026

Convention Center PH Free indoor parking

Convention Center PH Free indoor parking

4 out of 5
Downtown Baltimore
Save 100% on your flight
Price was $555, price is now $359 per person
$359
per person
Aug 13 - Aug 18
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
6/10 (1 review)
Hotel Burg

Hotel Burg

4 out of 5
Leesburg's Old and Historic District
Save 100% on your flight
Price was $1,002, price is now $653 per person
$653
per person
Aug 5 - Aug 11
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.6/10 Exceptional! (75 reviews)
Loved our time here - will definitely be coming back

Reviewed on Jun 22, 2026

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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

What to do in Chester

Epiphany

2 Hour Chesapeake Day Sail on Catamaran Epiphany

$245
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

$160
per adult
2-Hour Relaxing Chesapeake Day Sail on Lady Patty
See all activities in Chester

Chester Hotel Deals

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
$95 nightly
The price is $109 total per night from Jul 5 to Jul 6
$109 total
Jul 5 - Jul 6
Total with taxes and fees
8.6/10 Excellent! (1,001 reviews)
"Staff- The staff was mostly kind and helpful. I called the front desk to ask for a refill for the shower gel that was empty, and I was told, “No, we don’t have any.” No explanation, no apology, no alternative options, no . . . hospitality. Amenities-The toiletries (Crabtree & Evelyn) had a nice scent ..."

Reviewed on Jun 23, 2026

DoubleTree by Hilton Hotel Annapolis
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
$130 nightly
The price is $148 total per night from Jul 5 to Jul 6
$148 total
Jul 5 - Jul 6
Total with taxes and fees
9/10 Wonderful! (1,855 reviews)
"Very cute historic place to stay!"

Reviewed on Jun 24, 2026

Historic Inns of Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 out of 5
173 Jennifer Rd Annapolis MD
Fully refundable
$110 nightly
The price is $125 total per night from Jul 5 to Jul 6
$125 total
Jul 5 - Jul 6
Total with taxes and fees
8.8/10 Excellent! (1,007 reviews)
"This property could have done a bit more to offer breakfast and a more cleaner environment. I could have still seen that some spots were missed during the cleaning process."

Reviewed on Jun 25, 2026

Crowne Plaza Annapolis by IHG
See all 1,194 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.

Find the Best Chester Vacation Packages

Chester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Baltimore Washington Intl. Thurgood Marshall Airport (BWI)
Population
4,200
Top Sights
Sandy Point State Park, Sandy Point Beach and Matapeake State Park

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Frequently asked questions

How much does a Chester vacation package cost?
Offering great value package deals from $347 on Expedia, you'll be thrilled with how little a vacation to Chester costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Chester?
November, December and January are the best times to look for cheap Chester vacation packages. Opting to travel in quieter periods means you can typically find better prices on flights and hotels.
How many days is enough for Chester?
With a well-organized travel plan, you can easily hit the top Chester sights in a few days. But if you'd like to discover lesser-known spots or take day trips, consider booking your Chester vacation for longer.
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 vacation as a package?
Expedia vacation 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 customized Chester vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Chester?
If you're considering a spur-of-the-moment Chester vacation, 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.
Does Expedia offer Book Now, Pay Later Chester vacation packages?
If you're like us, you love discovering new places but are not a fan of the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the total cost of your Chester break across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.

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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.