Chester Vacations from $612

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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.
Homewood Suites by Hilton Arlington Rosslyn Key Bridge

Homewood Suites by Hilton Arlington Rosslyn Key Bridge

3 out of 5
Rosslyn
Save 100% on your flight
Price was $837, price is now $612 per person
$612
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
9.4/10 Exceptional! (1,004 reviews)
Incredible welcoming and attentive staff! Spotlessly clean room. Big comfortable king bed. We had the spacious suite with a full kitchen and sofa bed. Loved it. We were lucky to have a room not facing the busy highway. Our room was wonderfully quite. Free shuttle that will take you 1 mile to Rosslyn Metro Station. It's about a 15 minute walk back.

Reviewed on Mar 21, 2026

Placemakr Buzzard Point

Placemakr Buzzard Point

4 out of 5
Southwest
Save 100% on your flight
Price was $958, price is now $644 per person
$644
per person
Jun 4 - Jun 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
9.2/10 Wonderful! (157 reviews)
I loved my stay there. The staff was so nice and helpful. I would definitely stay again.

Reviewed on Mar 5, 2026

Landing at Bridge District

Landing at Bridge District

4 out of 5
Southeast
Save 100% on your flight
Price was $1,048, price is now $728 per person
$728
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
8/10 Very Good! (8 reviews)
Great property! The Landing staff went out of their way to make sure I was comfortable.

Reviewed on Jan 24, 2026

Kimpton Hotel Monaco Washington DC by IHG

Kimpton Hotel Monaco Washington DC by IHG

4.5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $940, price is now $670 per person
$670
per person
May 27 - May 31
found 22 hours ago
Roundtrip flight included
Boston (BOS) to Washington (DCA)
8.4/10 Very Good! (1,002 reviews)
Very nice hotel. Rooms are on the smaller side. Very convenient location.

Reviewed on Mar 21, 2026

Club Wyndham National Harbor

Club Wyndham National Harbor

3.5 out of 5
Save 100% on your flight
Price was $1,674, price is now $1,223 per person
$1,223
per person
May 7 - May 12
found 3 hours ago
Roundtrip flight included
Seattle (SEA) to Washington (DCA)
8.4/10 Very Good! (478 reviews)
Everything was top notch would differently stay again

Reviewed on Mar 9, 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

Get rates
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Waterfront Sunset Bayview: sleeps 6

Waterfront Sunset Bayview: sleeps 6

Chester MD
Get rates
Waterfront Sunset Bayview: sleeps 6
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
Fully refundableReserve now, pay when you stay
$178 nightly
The price is $203 total per night from Apr 12 to Apr 13
$203 total
Apr 12 - Apr 13
Total with taxes and fees
9.4/10 Exceptional! (1,002 reviews)
Fantastic

Reviewed on Mar 25, 2026

Graduate by Hilton Annapolis
See all 1,176 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 $612 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.