Chester Vacations from $304

Book a Hotel + Flight or Car together to unlock savings

Photo by Patricia Knorr
    deals illustration
    Better together
    Save up to $1,045 when you book a flight and hotel together*
    stays illustration
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration
    Rest easy
    Plan, book, and manage your trip all in one place

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.
DoubleTree Hotel Baltimore - BWI Airport

DoubleTree Hotel Baltimore - BWI Airport

4 out of 5
Save 100% on your flight
per person
Aug 25 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.4/10 Very Good! (1,364 reviews)
Clean. Friendly, helpful staff!

Reviewed on Jun 18, 2025

Canopy by Hilton Baltimore Harbor Point

Canopy by Hilton Baltimore Harbor Point

4 out of 5
Fells Point
Save 100% on your flight
per person
Aug 25 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9/10 Wonderful! (1,005 reviews)
Great modern building. Great views. Cute walkable areas nearby. Definitely staying here again next time!

Reviewed on Jun 18, 2025

Sagamore Pendry Baltimore

Sagamore Pendry Baltimore

5 out of 5
Fells Point
Save 100% on your flight
per person
Aug 25 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.4/10 Exceptional! (1,001 reviews)
Great property, beautiful amenities

Reviewed on Jun 22, 2025

Hilton Baltimore Inner Harbor

Hilton Baltimore Inner Harbor

4 out of 5
Downtown West
Save 100% on your flight
per person
Aug 25 - Aug 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.4/10 Very Good! (1,003 reviews)
I love this property.. so clean, nice atmosphere rooms nice, and clean..love the view to see the Baltimore Orioles Stadium,,,, love everything, I will be back!

Reviewed on May 29, 2025

SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Sep 13 - Sep 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
No reviews
Don't see what you're looking for?
See all available trips from Columbus to Chester
View all trips

Discover the most popular places to visit in Chester

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.

Chesapeake Exploration Center

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
$143 nightly
The price is $163 total per night from Jul 6 to Jul 7
$163 total
Jul 6 - Jul 7
Total includes taxes and fees
8.8/10 Excellent! (1,785 reviews)
"We loved the area as well as the hotel. It's a 4 minute walk from the waterfront and has a great view of the state capital building. My only complaint would be that the A/C for my room stop functioning on my fourth night. We were moved to another room and the A/C in that room also didn't work. They ..."

Reviewed on Jun 20, 2025

Historic Inns of Annapolis
Hilton Garden Inn Annapolis Downtown
Hilton Garden Inn Annapolis Downtown
3 out of 5
174 West Street, Annapolis, MD
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $119 total per night from Jul 21 to Jul 22
$119 total
Jul 21 - Jul 22
Total includes taxes and fees
8.4/10 Very Good! (1,007 reviews)
"Conveniently located and clean. Great prices"

Reviewed on Jun 19, 2025

Hilton Garden Inn Annapolis Downtown
Country Inn & Suites by Radisson, Annapolis, MD
Country Inn & Suites by Radisson, Annapolis, MD
3 out of 5
2600 Housley Road, Annapolis, MD
Fully refundable
$101 nightly
The price is $115 total per night from Jul 2 to Jul 3
$115 total
Jul 2 - Jul 3
Total includes taxes and fees
9/10 Wonderful! (1,003 reviews)
"Great room, parking, and breakfast"

Reviewed on Jun 20, 2025

Country Inn & Suites by Radisson, Annapolis, MD
See all 1,239 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

More vacations you might like

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Chester vacation package cost?
Offering great value package deals from $304 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.