Chester Vacations from $288
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Furnished Apartments
Ashton Heights
$745
per person
Sep 9 - Sep 14
found 22 hours ago
Roundtrip flight included
Atlanta (ATL) to Baltimore (BWI)
9/10 Wonderful! (4 reviews)
Location is excellent. Walking distance to pretty much everything you need. Space was very comfortable, clean, and the bed was excellent for sleeping. Lots of light and windows.
Host was helpful and able to accommodate my schedule needs too.
Reviewed on Apr 1, 2025
Stay near popular Chester attractions
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.
Chester Hotel Deals
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
$98 nightly
$111 total
Aug 30 - Aug 31
Total with taxes and fees
8.8/10 Excellent! (1,090 reviews)
"Property was clean but a bit dated , staff was exceptional, AC was loud"
Reviewed on Aug 9, 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
$132 nightly
$150 total
Aug 17 - Aug 18
Total with taxes and fees
9/10 Wonderful! (1,940 reviews)
"Great hotel in a great city."
Reviewed on Aug 10, 2026
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
Fully refundable
$110 nightly
$125 total
Sep 1 - Sep 2
Total with taxes and fees
8.8/10 Excellent! (1,018 reviews)
"Room was clean but a few things were broken. Toilet paper holder broken, cabinet door for the cupboard of the refrigerator broken. Called for maintenance and they came right away. Pool area VERY small hot tub broken. No one used the pool area..looked dirty. Workout room ok, treadmill worked as expected. ..."
Reviewed on Aug 10, 2026
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 |
More vacations you might like
Frequently asked questions
How much does a Chester vacation package cost?
Offering great value package deals from $288 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.
Explore a world of travel with Expedia
- Annapolis Hotels
- Maryland Hotels
- National Harbor Hotels
- Cheap Hotels in Maryland
- Hotels with Free Airport Shuttle in Baltimore
- Stevensville Hotels
- St. Michaels Hotels
- Inner Harbor Hotels
- Cabin Rentals in Maryland
- All-Inclusive Resorts in Maryland
- Baltimore Hotels
- Cheap Hotels in Baltimore
- Hotels near Baltimore Washington Intl. Thurgood Marshall
- Oceanfront Hotels in Annapolis
- Washington Hotels
- Cheap Hotels in Washington
- Beach Hotels in Maryland
- Flights from Atlanta (ATL) to Baltimore (BWI)
- Flights from Baltimore Washington Intl. Thurgood Marshall
- Flights from Raleigh (RDU) to Baltimore (BWI)
- Flights from Orlando (MCO) to Baltimore (BWI)
- Flights to Washington
- Flights from Houston (IAH) to Baltimore (BWI)
- Flights from Seattle (SEA) to Baltimore (BWI)
- Flights from Boston (BOS) to Baltimore (BWI)
- Flights from San Diego (SAN) to Baltimore (BWI)
- Flights from Denver (DEN) to Baltimore (BWI)
- Flights to Annapolis
- Flights from Miami (MIA) to Baltimore (BWI)
- Flights from Charlotte (CLT) to Baltimore (BWI)
- Flights from Phoenix (PHX) to Baltimore (BWI)
- Flights from Tampa (TPA) to Baltimore (BWI)
- Flights from Minneapolis (MSP) to Baltimore (BWI)
- Flights from New York (JFK) to Baltimore (BWI)
- Flights from Los Angeles (LAX) to Baltimore (BWI)
- Flights from Detroit (DTW) to Baltimore (BWI)
- Flights from Fort Lauderdale (FLL) to Baltimore (BWI)
- Flights from Chicago (ORD) to Baltimore (BWI)
- Flights to Maryland
- Flights from San Francisco (SFO) to Baltimore (BWI)
- Flights from Dallas (DFW) to Baltimore (BWI)
- Flights to Baltimore
- Baltimore Maritime Museum
- Annapolis Vacations
- Robert Long House
- Kunta Kinte–Alex Haley Memorial
- Baltimore American Indian Center
- The Colonial Players
- Maryland Vacations
- U.s. Naval Academy Golf Club
- University of Maryland Medical Center
- National Aquarium in Baltimore
- Hammond-Harwood House
- Uscg Lightship Chesapeake
- The Phoenix Shot Tower
- St. Mary's Spiritual Center and Historic Site
- Chesapeake Bay Bridge
- U.s. Naval Academy
- Hopkins Plaza
- Ellen O. Moyer Nature Park at Back Creek
- Queenstown Vacations
- Annapolis City Dock
- Sandy Point State Park
- Thurgood Marshall Memorial
- Visit Annapolis
- Maryland State House
- Oriole Park at Camden Yards
- Queenstown Premium Outlets
- Maryland Women's Heritage Center
- Maryland Quiet Waters Park
- Ego Alley
- Baltimore Vacations
- Holocaust Memorial
- Rock Hall Harbor
- Navy-Marine Corps Memorial Stadium
- Ferry Park
- Federal Hill Vacations
- Chesapeake Bay Environmental Center
- Eubie Blake National Jazz Institute and Cultural Center
- National Historic Seaport of Baltimore
- Washington Vacations
- Baltimore City Hall
- Bay Bridge Market Place Shopping Center
- Visit Maryland
- Uss Constellation
- Annapolis Maritime Museum
- Baltimore Convention Center
- Under Sky One Family Sculpture
- Maryland World War II Memorial
- William Paca House
- Charm'tastic Mile
- Visit Washington
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
