Chester Vacation Packages
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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!
Top Chester Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Kellogg Conference Hotel at Gallaudet University
Northeast
CA $615
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
8.4/10 Very good! (1,006 reviews)
Great staff. Nice rooms. Free diffused ice water. Know that this hotel is on the Gallaudet campus, a deaf university. Has a shuttle to Union station. Plan your excursions on that time. The nearest metro stop is an easy 15 minute walk as an alternative
Reviewed on Aug 15, 2026
Ready to book your vacation to Chester?
Chester Hotel Deals
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
CA $135
CA $154 total
Aug 30 - Aug 31
includes taxes & fees
8.8/10 Excellent! (1,098 reviews)
"This is our favorite hotel to stay in while in the Annapolis area. The hotel is clean inside and out. Staff are so wonderful and genuinely care about your happiness. And a price point that trumps other hotels by far. We've stayed at another hotel that is right beside this one and were very disappointed, ..."
Reviewed on Aug 16, 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
CA $127
CA $193 total
Aug 25 - Aug 26
includes taxes & fees
9/10 Wonderful! (1,942 reviews)
"Unique and historic hotel with quaint rooms and well decorated period common spaces. Friendly staff and very clean."
Reviewed on Aug 16, 2026
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
Fully refundable
CA $143
CA $163 total
Sep 15 - Sep 16
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Very clean and classy place."
Reviewed on Aug 16, 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.
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.
Frequently asked questions
How much does a Chester vacation package cost?
Offering excellent value package deals from CA $615 on Expedia, you'll be pleasantly surprised at how much a vacation to Chester costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Chester?
Travel in the off-peak season and you're likely to score cheap Chester vacation packages. Keep in mind that school vacation periods and local festivals and events can impact prices, so do a little research before you go.
How many days is enough for Chester?
When planning your Chester vacation, a handful of days will be enough to see all the highlights. Be sure to stop by Eastern Neck National Wildlife Refuge — it's one of the major attractions in this destination. If you want more adventure, consider basing yourself here and setting off on some tours from Chester.
How to find the best Chester package deals?
Use Expedia's handy filters to help you find some terrific Chester package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or search for Chester package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Chester vacation as a package?
You can enjoy significant savings on your Chester escape by booking a customized vacation package. Check the "Package" heading, then select your destination and travel dates to see the best flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Chester?
If you've got your Chester vacation dates locked in, book as soon as you can to bag some fantastic deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Chester?
- Choose your dates: What you plan to do in Chester and your favourite season will help you decide when to go.
- Plan your budget wisely: Besides the cost of your accommodations, you'll need to factor in other expenses too. These include transportation, food and flights. Also, put aside a little extra for unexpected expenses that could arise during your trip to Chester.
- Determine how many days away: Start by compiling a list of the sights and activities you'd like to experience in Chester. Then, estimate how long you'll need for each, as well as any travel time.
- Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to choose a Chester vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
