Chester Vacations from $363

Book a Hotel + Flight or Car together to unlock savings

Photo by Patricia Knorr

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

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

  • 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.
Comfort Inn & Suites Baltimore Inner Harbor

Comfort Inn & Suites Baltimore Inner Harbor

3 out of 5
Downtown Baltimore
Price was $557, price is now $363 per person
$363
per person
Oct 25 - Oct 28
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Baltimore (BWI)
5.2/10 (1,014 reviews)
For the price I was very pleased. The room was very spacious

Reviewed on Aug 5, 2026

Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Save 100% on your flight
Price was $952, price is now $557 per person
$557
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.4/10 Very Good! (1,004 reviews)
I love that it’s located on university campus, great for family bringing students from out of state.

Reviewed on Aug 5, 2026

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $1,282, price is now $770 per person
$770
per person
Sep 6 - Sep 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9/10 Wonderful! (1,218 reviews)

The LINE Hotel DC

The LINE Hotel DC

4.5 out of 5
Northwest
Save 100% on your flight
Price was $597, price is now $378 per person
$378
per person
Oct 15 - Oct 18
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.6/10 Excellent! (1,003 reviews)

Hotel Burg

Hotel Burg

4 out of 5
Leesburg's Old and Historic District
Save 100% on your flight
Price was $1,605, price is now $1,034 per person
$1,034
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
9.6/10 Exceptional! (100 reviews)
Excellent service and hospitality. Beautiful and clean. Would come back here many times. Friendly and professional staff. It was a great experience.

Reviewed on Aug 4, 2026

Don't see what you're looking for?
See all available trips from Columbus to Chester
View all trips

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

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
$98 nightly
The price is $111 total per night from Aug 30 to Aug 31
$111 total
Aug 30 - Aug 31
Total with taxes and fees
8.8/10 Excellent! (1,077 reviews)
"Convient location. Nice amenities including dog friendly, hugh pool. Full service restaurant. Shuttle that takes you around town to downtown and surrounding 5 mile radius which was a nice bonus."

Reviewed on Aug 5, 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
$132 nightly
The price is $150 total per night from Aug 19 to Aug 20
$150 total
Aug 19 - Aug 20
Total with taxes and fees
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
$118 nightly
The price is $135 total per night from Aug 9 to Aug 10
$135 total
Aug 9 - Aug 10
Total with taxes and fees
8.8/10 Excellent! (1,012 reviews)
"This was an amazing stay! My room got serviced daily while I was out exploring and they kept everything nice and clean! The breakfast add on was so worth it so if you have the option to definitely add it! I had an amazing time and can’t wait to stay again!"

Reviewed on Aug 3, 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.

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 $363 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.

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.