Chester Vacations from $252

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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.
DoubleTree Hotel Baltimore - BWI Airport

DoubleTree Hotel Baltimore - BWI Airport

4 out of 5
Save 100% on your flight
Price was $358, price is now $252 per person
$252
per person
Apr 30 - May 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
8.4/10 Very Good! (1,244 reviews)
The cover on the heater is missing the foam weatherstripping. There’s a little on the left side but none on the right side. Felt like a cold window was open. I resolved it for my stay by placing a folded bath towel on top of the heater. You should repair this so the next guests don’t freeze.

Reviewed on Mar 4, 2026

Pendry Baltimore

Pendry Baltimore

5 out of 5
Fells Point
Save 100% on your flight
Price was $2,223, price is now $1,388 per person
$1,388
per person
Apr 24 - Apr 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9.4/10 Exceptional! (1,000 reviews)
Nice room, clean view of the water.

Reviewed on Feb 20, 2026

The Normandy Hotel

The Normandy Hotel

3 out of 5
Northwest
Save 100% on your flight
Price was $532, price is now $335 per person
$335
per person
Apr 25 - Apr 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.6/10 Excellent! (1,002 reviews)
The property is easy walking distance from Dupont Circle north station. The room was clean and well decorated. There is a wonderful seating/cafe dining area on the ground floor that includes a library, a sunroom, and an outdoor seating area. Every morning a wonderful european style breakfast is served including cheese, lunch meets, yogurt, hardboiled eggs, waffles, toast, jam, fruit, cereal and a variety of bread. Every evening at 5pm, a cheese and cracker with wine or coffee/tea is served for a nice pre-dinner appetizer when you return from being out fo the day. The inn is very relaxing and quaint in a neighborhood filled with embassies. The gold gym pass is also a plus. The inn is wonderful for vacation or business uses.

Reviewed on Mar 5, 2026

InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
Southwest
Save 100% on your flight
Price was $975, price is now $649 per person
$649
per person
May 28 - May 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.4/10 Exceptional! (1,066 reviews)
The proximity of the hotel to the Anthem is amazing! A one minute walk and lots of restaurants nearby. Lovely hotel and helpful staff.

Reviewed on Mar 6, 2026

The Churchill Hotel near Embassy Row

The Churchill Hotel near Embassy Row

4 out of 5
Northwest
Save 100% on your flight
Price was $851, price is now $593 per person
$593
per person
Apr 7 - Apr 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
8.8/10 Excellent! (1,915 reviews)
Staff was professional, helpful, and friendly!

Reviewed on Feb 16, 2026

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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

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Chester MD
10/10 Exceptional! (126 reviews)
Perfect vacation home....large and comfortable.....relaxing, peaceful, close to bike trails, a great homebase for sightseeing many small towns...loved meeting the homeowner, very friendly..

Reviewed on Sep 14, 2025

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Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
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
$157 nightly
The price is $179 total per night from Apr 2 to Apr 3
$179 total
Apr 2 - Apr 3
Total with taxes and fees
9/10 Wonderful! (1,880 reviews)
Staff were a pleasure. Room was beautiful.

Reviewed on Mar 4, 2026

Historic Inns of Annapolis
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
$89 nightly
The price is $102 total per night from Mar 15 to Mar 16
$102 total
Mar 15 - Mar 16
Total with taxes and fees
8.6/10 Excellent! (1,014 reviews)
I stayed here as I did a visit for my youngest son who is attending Bowie. While I stayed most of the time on campus, I found when I was at the hotel I found the staff and facility both inviting, warm and cordial.

Reviewed on Mar 5, 2026

DoubleTree by Hilton Hotel Annapolis
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 $252 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.