Chester Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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!
Top Chester Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Hive
Northwest
CA $1,358
per person
Nov 15 - Nov 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
9.4/10 Exceptional! (1,630 reviews)
Great location near the Metro and right next to GWU, in an area that felt very safe. Major sights were easy to get to. The bed was so comfortable that I’m seriously considering replacing mine at home with the same brand!
Reviewed on Oct 14, 2026
Holiday Inn National Airport/Crystal City by IHG
Crystal City
CA $1,148
per person
Nov 15 - Nov 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
8.2/10 Very good! (1,946 reviews)
Room was clean and everything functioned properly. Location of the hotel is very convenient for getting around the area. Only improvement would’ve been having a mini fridge in the room. Good stay overall.
Reviewed on Oct 14, 2026
Ready to book your vacation to Chester?
Chester Hotel Deals
Graduate by Hilton Annapolis
126 West St Annapolis MD
CA $209
CA $238 total
Oct 26 - Oct 27
includes taxes & fees
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
CA $151
CA $172 total
Oct 18 - Oct 19
includes taxes & fees
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
CA $153
CA $174 total
Nov 11 - Nov 12
includes taxes & fees
8.8/10 Excellent! (1,008 reviews)
"Clean room. Great breakfast."
Reviewed on Oct 13, 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.
What to do in Chester
St Michaels: 2-Hour Chesapeake Bay Sail on Lady Patty
CA $222
per adult
2 Hour Chesapeake Day Sail on Catamaran Epiphany
CA $343
per adult
St. Michaels: 2-Hour Relaxing Chesapeake Sail on Epiphany
CA $378
per adult
Frequently asked questions
How much does a Chester vacation package cost?
Offering excellent value package deals from CA $920 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.
