Chester Vacations from $446

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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.
The Normandy Hotel

The Normandy Hotel

3 out of 5
Northwest
Save 100% on your flight
Price was $677, price is now $446 per person
$446
per person
May 26 - May 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
8.6/10 Excellent! (1,006 reviews)
I do not welcome pets into my home. When I travel, pets should be outside not inside where am. Each staff person was wonderful. The included breakfast and wine/cheese events are very enjoyable and why I choose Normandy! Thanks.

Reviewed on Mar 7, 2026

Phoenix Park Hotel

Phoenix Park Hotel

3.5 out of 5
Northwest
Save 100% on your flight
Price was $1,481, price is now $1,028 per person
$1,028
per person
Apr 14 - Apr 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.4/10 Exceptional! (2,213 reviews)
Room was very nice and staff was excellent - super friendly and helpful.

Reviewed on Mar 5, 2026

Riggs Washington DC

Riggs Washington DC

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was $1,051, price is now $736 per person
$736
per person
May 26 - May 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.4/10 Exceptional! (1,416 reviews)
Everything was beautiful and everyone I encountered was so nice and helpful!

Reviewed on Mar 9, 2026

Hyatt Place Arlington/Courthouse Plaza

Hyatt Place Arlington/Courthouse Plaza

3 out of 5
Court House
Save 100% on your flight
Price was $1,289, price is now $907 per person
$907
per person
Apr 14 - Apr 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.2/10 Wonderful! (1,062 reviews)
The location is unbeatable, near restaurants and right by the metro stop. We had the king room on a high floor which was nice and spacious, however the hvac system in the room is super loud! When it goes on it sounds like an engine is running in the room, even with earplugs we could hear it and it disrupted our sleep. Also, the bathroom sink faucet was loose and wobbly, every time you turned it on it felt like it was going to fall out. In addition, the shower water pressure is barely more than a trickle, but the water was hot. If you want an amazing location this is the place, but the hotel def needs some TLC.

Reviewed on Mar 9, 2026

Hotel Hive

Hotel Hive

3.5 out of 5
Northwest
Save 100% on your flight
Price was $1,473, price is now $1,062 per person
$1,062
per person
Apr 14 - Apr 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Washington (DCA)
9.2/10 Wonderful! (1,368 reviews)
Super easy check in experience. Friendly staff. Room was super well presented. Only issue was the fire alarm went off mid-stay for seemingly no reason. Shower also only got medium-warm and not really ever hot, but it was fine.

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 Sunset Bayview: sleeps 6

Waterfront Sunset Bayview: sleeps 6

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

Graduate by Hilton Annapolis

4 out of 5
126 West St Annapolis MD
Fully refundableReserve now, pay when you stay
$169 nightly
The price is $193 total per night from Mar 29 to Mar 30
$193 total
Mar 29 - Mar 30
Total with taxes and fees
9.4/10 Exceptional! (1,005 reviews)
Lovely and fun theme hotel. Staff was wonderdul

Reviewed on Mar 8, 2026

Graduate by Hilton 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 $446 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.