Chester Vacations from $289
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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
- Convention center Indoor free parking
Jan 12 - Jan 17Convention center Indoor free parking + Flight
Downtown Baltimore5 nights4.0 star propertyRoundtrip • Atlanta (ATL) - Baltimore (BWI)ATL - BWI • Nonstop BWI - ATL • Nonstop$462$289found 1 day agoper traveler - Harbor free indoor parking
Jan 12 - Jan 17Harbor free indoor parking + Flight
Downtown Baltimore5 nights4.0 star propertyRoundtrip • Atlanta (ATL) - Baltimore (BWI)ATL - BWI • Nonstop BWI - ATL • Nonstop$718$438found 1 day agoper traveler - Eurostars Saint Gregory Dupont Circle Georgetown
Jan 20 - Jan 25Eurostars Saint Gregory Dupont Circle Georgetown + Flight
Downtown Washington D.C.5 nights4.0 star property8.6/10 - Excellent (1,005 reviews)Roundtrip • Atlanta (ATL) - Baltimore (BWI)ATL - BWI • Nonstop BWI - ATL • Nonstop - The Potomac Hotel, Autograph Collection
Feb 4 - Feb 7The Potomac Hotel, Autograph Collection + Flight
Southwest3 nights5.0 star property9.4/10 - Exceptional (1,065 reviews)"This a beautiful property! Rooms are huge! Great place to stay."Reviewed November 9, 2026Roundtrip • Atlanta (ATL) - Baltimore (BWI)ATL - BWI • Nonstop IAD - ATL • Nonstop$731$472found 1 day agoper traveler - Sofitel Washington DC Lafayette Square
Feb 4 - Feb 7Sofitel Washington DC Lafayette Square + Flight
Downtown Washington D.C.3 nights5.0 star property9.0/10 - Wonderful (1,300 reviews)"Rooms were short on closet space and no dressers to put clothes for an 8 day stay"Reviewed November 9, 2026Roundtrip • Atlanta (ATL) - Baltimore (BWI)ATL - BWI • Nonstop IAD - ATL • Nonstop$575$374found 1 day agoper traveler
Where to stay near Chester
Stevensville
Discover Stevensville, a welcoming destination perfectly suited for travelers seeking a blend of business, family, and outdoor experiences. This charming city offers easy access to attractions like the Chesapeake Bay Bridge and Sandy Point State Park, where you can enjoy scenic views and beach activities. With its proximity to Chester, just about a mile away by car, Stevensville is a smart choice for your stay, providing a great base for a memorable getaway.
Annapolis
Experience the charm of Annapolis, a delightful hub for family travelers and weekend getaways who want to explore its rich history and stunning waterfront. With attractions like the Chesapeake Bay Bridge, Sandy Point State Park, and the Annapolis Maritime Museum, visitors can enjoy a mix of outdoor activities and cultural experiences. Located about 18 miles by car from Chester, Annapolis offers easy access to a vibrant atmosphere, making it a smart choice for your stay.
Kent Narrows
If you are an outdoor enthusiast or a family traveler, look no further than Kent Narrows, known for its stunning Chesapeake Bay views and vibrant beach experiences. This charming village offers easy access to attractions like the Chesapeake Bay Environmental Center and Sandy Point State Park, perfect for enjoying the great outdoors. Located about 3 miles by car from Chester, Kent Narrows makes for a smart choice for your stay, combining relaxation with ample opportunities for adventure.
Kent Island
Kent Island stands out as a prime spot for outdoor enthusiasts and families interested in a scenic getaway. With its beautiful beaches, stunning views of the Chesapeake Bay, and access to attractions like Sandy Point State Park and the Chesapeake Bay Bridge, visitors can enjoy a variety of activities year-round. Located about 3 miles from Chester, Kent Island offers a perfect blend of relaxation and adventure, making it a smart choice for your next vacation.
Grasonville
Travelers visiting the area often choose Grasonville, especially those with an affinity for outdoor adventures and family-friendly experiences. This charming city offers easy access to the stunning Chesapeake Bay, the serene Eastern Neck National Wildlife Refuge, and the educational Chesapeake Bay Environmental Center. With its vibrant boardwalk and shopping options, Grasonville is a delightful base for exploring nearby Chester, located about 4 miles away. Enjoy a memorable stay in Grasonville, where diverse activities await you.
What to do in Chester
St Michaels: 2-Hour Chesapeake Bay Sail on Lady Patty
2 Hour Chesapeake Day Sail on Catamaran Epiphany
St. Michaels: 2-Hour Relaxing Chesapeake Sail on Epiphany
Chester Hotel Deals
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHG"Staff was very friendly."
Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & Marina
Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island Marina"Coffee in the breakfast area was terrible. Weak and watery. Thta' might seem like a minor factor. but for those of us who appreciate a good, strong cup of coffee, it's a problem."
Quality Inn Grasonville near Kent Island
Quality Inn Grasonville near Kent Island"The staff was very friendly and helpful. We will be back."
The Inn at Chesapeake Bay Beach Club
The Inn at Chesapeake Bay Beach Club"The perfect getaway weekend with my husband! Will definitely go back."
"We liked the location of inn which was near Main St and the dock area"
"We had a balcony that was private to our room. Because it was the off season, we were the only ones that stayed there. Had the whole place to ourselves."
Frequently Asked Questions
How much does a Chester vacation package cost?
Offering great value package deals from $289 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.