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.
InterContinental Washington D.C. - The Wharf by IHG
The Wharf
CA $920
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Baltimore (BWI)
9.4/10 Exceptional! (1,226 reviews)
This is a beautiful property in a great location. All the staff from the concierge, doorman, and front desk were all friendly and welcoming. We had a great stay. We come to DC often and decided based on this visit this is our new go to place.
Reviewed on Oct 15, 2026
Riggs Washington DC
Downtown Washington D.C.
CA $1,667
per person
Nov 17 - Nov 20
found 3 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Baltimore (BWI)
9.4/10 Exceptional! (1,415 reviews)
I want to love this property because staff are amazing (although everyone appears to be younger and I’m sensitive to age discrimination) and location really works for me but there are some obvious flaws… the large awkward inner bathroom door being the first, a floating column in the room being another, lighting being yet another (bathroom lighting is awful… too bright, no nightlight sensor), impossible to read bodycare labels, and poorly operable hairdryer and clothing steamer. Bed and linens are good quality, appreciate the complimentary bottled water, and loved the breakfast options and drinks menu (but quality of mixed drinks was uneven). This was my second time here and service has notched up but some things are not keeping up with recent trends and comfort. Still a better than average experience.
Reviewed on Oct 14, 2026
Mint House Washington DC Downtown by Kasa
Downtown Washington D.C.
CA $1,468
per person
Nov 17 - Nov 20
found 3 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Baltimore (BWI)
9.6/10 Exceptional! (214 reviews)
Great location. Close to metro and bus routes so easy to get around the city. Room was spacious and nice to have the kitchen available.
Reviewed on Oct 15, 2026
Ready to book your vacation to Chester?
Chester Hotel Deals
Graduate by Hilton Annapolis
126 West St Annapolis MD
Fully refundableReserve now, pay when you stay
CA $209
CA $238 total
Oct 26 - Oct 27
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
"Good"
Reviewed on Oct 15, 2026
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
CA $150
CA $172 total
Oct 18 - Oct 19
includes taxes & fees
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
Fully refundable
CA $156
CA $178 total
Oct 25 - Oct 26
includes taxes & fees
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.
