Chester Vacations from $285
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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.
Kellogg Conference Hotel at Gallaudet University
Northeast
$285
per person
Oct 22 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.4/10 Very Good! (1,006 reviews)
Please put more wash cloths & towels in the bathrooms thanks!!
Reviewed on Aug 10, 2026
Club Quarters Hotel in Washington DC
Downtown Washington D.C.
$913
per person
Oct 11 - Oct 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9/10 Wonderful! (2,006 reviews)
Overall we had a great experience at the hotel, room was well maintained, clean and ready after returning tired from various trips. Staff was friendly and eager to help and accommodate.
Reviewed on Aug 10, 2026
Hotel Burg
Leesburg's Old and Historic District
$1,102
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Baltimore (BWI)
9.6/10 Exceptional! (105 reviews)
Everything was excellent with our stay at Hotel Burg, the staff was helpful and attentive, the room was clean and well furnished, the lounge and roof top bar had a great ambiance and excellent menu. We are excited to return again!
Reviewed on Aug 10, 2026
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.
Chester Hotel Deals
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
$98 nightly
$111 total
Aug 30 - Aug 31
Total with taxes and fees
8.8/10 Excellent! (1,090 reviews)
"Property was clean but a bit dated , staff was exceptional, AC was loud"
Reviewed on Aug 9, 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
$132 nightly
$150 total
Aug 17 - Aug 18
Total with taxes and fees
9/10 Wonderful! (1,943 reviews)
"The staff waited until exactly 04:00 to check us in. There were blood stains in our room. The mattress did not have a cover, had to use the linens."
Reviewed on Aug 11, 2026
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
Fully refundable
$110 nightly
$125 total
Sep 1 - Sep 2
Total with taxes and fees
8.8/10 Excellent! (1,020 reviews)
"We had a great time at this hotel. Room was clean and cozy we spent time in the pool which did look bigger in the pictures but we still had fun. I would definitely stay again."
Reviewed on Aug 10, 2026
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 $285 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.
