Chester Vacations from $237

Book a Hotel + Flight or Car together to unlock savings

Photo by Patricia Knorr

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
Price was $425, price is now $237 per person
$237
per person
Jan 21 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Washington (DCA)
8/10 Very Good! (1,099 reviews)
Very clean and comfortable

Reviewed on Nov 9, 2025

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 $806, price is now $433 per person
$433
per person
Jan 21 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Washington (DCA)
9/10 Wonderful! (1,074 reviews)
Room was spotless and comfortable and quiet. All staff were very friendly and helpful. Great location to walk to the Metro and restaurants and the White House!

Reviewed on Oct 28, 2025

Hilton Washington DC Capitol Hill

Hilton Washington DC Capitol Hill

4 out of 5
Northwest
Save 100% on your flight
Price was $896, price is now $520 per person
$520
per person
Jan 21 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Washington (DCA)
9/10 Wonderful! (1,011 reviews)
Rooms very clean, staff very friendly and professional.

Reviewed on Nov 7, 2025

Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Save 100% on your flight
Price was $636, price is now $373 per person
$373
per person
Jan 21 - Jan 26
found 5 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Washington (DCA)
8.2/10 Very Good! (1,005 reviews)
It was a peaceful place to stay and affordable for DC

Reviewed on Nov 4, 2025

Embassy Suites by Hilton Washington D.C. – Convention Center

Embassy Suites by Hilton Washington D.C. – Convention Center

3.5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $687, price is now $406 per person
$406
per person
Jan 21 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Washington (DCA)
9.2/10 Wonderful! (2,000 reviews)
Good hotel . Perfect for visiting DC and with family

Reviewed on Nov 9, 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
$145 nightly
The price is $166 total per night from Nov 17 to Nov 18
$166 total
Nov 17 - Nov 18
Total with taxes and fees
8.8/10 Excellent! (1,874 reviews)
Beautiful

Reviewed on Nov 5, 2025

Historic Inns of 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
$93 nightly
The price is $106 total per night from Dec 7 to Dec 8
$106 total
Dec 7 - Dec 8
Total with taxes and fees
8.8/10 Excellent! (1,007 reviews)
Came in late at night and left early the Inn was quiet, safe, comfortable and clean. Ice maker on 1st floor was out of order but there is a second one. Staff was attentive and helpful when we came in and check in was quick and easy. Would stay here again for other local sporting events.

Reviewed on Nov 8, 2025

Country Inn & Suites by Radisson, Annapolis, MD
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

3 out of 5
170 Admiral Cochrane Dr, Edgewater, MD
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $95 total per night from Nov 30 to Dec 1
$95 total
Nov 30 - Dec 1
Total with taxes and fees
8.8/10 Excellent! (940 reviews)
All of the above and more. Spotless room and extraordinary staff!

Reviewed on Nov 8, 2025

Sonesta ES Suites Annapolis
See all 1,220 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 $237 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.