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.
Hotel Arboretum

Hotel Arboretum

2 out of 5
Northeast
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Washington (DCA)
8/10 Very Good! (968 reviews)
Staff was nice. Hotel is in deperate need of an upgrade

Reviewed on Aug. 10, 2025

The Churchill Hotel near Embassy Row

The Churchill Hotel near Embassy Row

4 out of 5
Northwest
per person
Oct 13 - Oct 17
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Washington (DCA)
8.8/10 Excellent! (1,821 reviews)
Bed was good food ok expensive

Reviewed on Aug. 11, 2025

Club Quarters Hotel in Washington DC

Club Quarters Hotel in Washington DC

3 out of 5
Downtown Washington D.C.
per person
Oct 13 - Oct 17
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Washington (WAS)
8.8/10 Excellent! (1,624 reviews)
Second floor of the hotel was super noisy, could hear doors slamming, traffic, people shouting and water running in other rooms.

Reviewed on Aug. 10, 2025

Hampton Inn & Suites Washington DC-Navy Yard

Hampton Inn & Suites Washington DC-Navy Yard

3 out of 5
Navy Yard
per person
Sep 22 - Sep 26
found 18 hours ago
Roundtrip flight included
Toronto (YYZ) to Washington (WAS)
8.8/10 Excellent! (1,003 reviews)
Great hotel. Always our go to location when attending a Nationals game. Suite was wonderful. Great view of the stadium and the water.

Reviewed on Aug. 3, 2025

YOTEL Washington DC

YOTEL Washington DC

4 out of 5
Northwest
per person
Oct 13 - Oct 17
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Washington (WAS)
8.2/10 Very Good! (2,041 reviews)
Property was beautiful but a little bit over priced. Still a fabulous facility though

Reviewed on Aug. 12, 2025

Ready to book your vacation to Chester?

 

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Chester Hotel Deals

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!

Chester
9.8/10 Exceptional! (92 reviews)
Great location for a relaxing, fun, family vacation
"Our family (ages 16 - 73) enjoyed our week here very much. Harry and Scott were great to work with and were always available to answer questions. We were aiming for a relaxing, low key week so we didn't stray too far from the house for adventures, but that just goes to show we had everything we needed ..."

Reviewed on Aug. 8, 2025

Get rates
Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is CA $140 per night from Aug 25 to Aug 26
CA $140
CA $207 total
Aug 25 - Aug 26
includes taxes & fees
8.8/10 Excellent! (1,821 reviews)
"Property was well maintained, very close to shopping and dining. Everything within walking distance. Was a great time."

Reviewed on Aug. 10, 2025

Historic Inns of Annapolis
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is CA $221 per night from Sep 2 to Sep 3
CA $221
CA $252 total
Sep 2 - Sep 3
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
"Beautiful hotel in a great location!"

Reviewed on Aug. 10, 2025

Graduate by Hilton Annapolis
See all 1,239 properties in Chester
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.
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Discover the most popular places to visit in Chester

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.

Chesapeake Exploration Center

Frequently asked questions

How much does a Chester vacation package cost?
Offering excellent value package deals from CA $480 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?

  1. Choose your dates: What you plan to do in Chester and your favourite season will help you decide when to go.
  2. 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.
  3. 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.
  4. 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.