Chester Vacations from $211

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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.
Hotel Arboretum

Hotel Arboretum

2 out of 5
Northeast
Save 100% on your flight
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8/10 Very Good! (944 reviews)
Bed very comfortable and bedding looked and felt clean and in very good condition. Very impressed with the cleanliness and condition of the room and property- I’ve paid much more for much, much less. 10/10

Reviewed on Aug 6, 2025

The St. Gregory Hotel

The St. Gregory Hotel

4 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.6/10 Excellent! (1,004 reviews)
My stay was very pleasant

Reviewed on Jul 27, 2025

SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.8/10 Exceptional! (25 reviews)
Absolutely incredible hotel that we happened upon on a whim. Brand new, absolutely stunning and Johnny the concierge made our night and had us feeling right at home despite the grandeur of the establishment. Can’t recommend this place enough and shout out to Johnny ❤️

Reviewed on Aug 3, 2025

The Graham Georgetown

The Graham Georgetown

4 out of 5
Northwest
Save 100% on your flight
per person
Oct 9 - Oct 15
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Washington (WAS)
8.8/10 Excellent! (1,706 reviews)
Location was perfect! I spent more the night before for a higher ranked hotel in sketchy area. I consider this hotel to be a true 5 star. The restaurant recommendation, I would have never found. The kitchen closed late and we arrived when kitchens in the area were closing. It was memorable with my teenage daughter. I will never stay anywhere else if in DC. Beds were amazing! Thank you!

Reviewed on Aug 5, 2025

Hilton McLean Tysons Corner

Hilton McLean Tysons Corner

4 out of 5
Save 100% on your flight
per person
Oct 10 - Oct 13
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.6/10 Excellent! (1,000 reviews)
Restaurant options limited

Reviewed on Aug 3, 2025

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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 Aug 17 to Aug 18
$163 total
Aug 17 - Aug 18
Total includes taxes and fees
8.8/10 Excellent! (1,824 reviews)
"We’ve been here a few times and continue to to love the location, staff and comfortable beds."

Reviewed on Aug 4, 2025

Historic Inns of Annapolis
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St, Annapolis, MD
Fully refundableReserve now, pay when you stay
$155 nightly
The price is $177 total per night from Aug 17 to Aug 18
$177 total
Aug 17 - Aug 18
Total includes taxes and fees
9.4/10 Exceptional! (1,005 reviews)
"We had a wonderful stay at THE GRADUATE. We will definitely return when we visit Annapolis."

Reviewed on Aug 6, 2025

Graduate by Hilton Annapolis
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
$97 nightly
The price is $110 total per night from Aug 13 to Aug 14
$110 total
Aug 13 - Aug 14
Total includes taxes and fees
9/10 Wonderful! (1,009 reviews)
"Property grounds was very good and had a lot of amenities nearby. Staff was very nice and accommodating. The pool on property was amazing."

Reviewed on Aug 4, 2025

Country Inn & Suites by Radisson, Annapolis, MD
See all 1,246 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.

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Frequently asked questions

How much does a Chester vacation package cost?
Offering great value package deals from $211 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.