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 25 - Sep 28
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
8/10 Very Good! (848 reviews)
solid stay for the price point

Reviewed on Jul. 26, 2025

SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
per person
Sep 25 - Sep 28
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
10/10 Exceptional! (12 reviews)
Very nice and clean hotel, very friendly team, neat and impressive technology equipped rooms, I would highly recommend it to friends and family

Reviewed on Jul. 25, 2025

Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
per person
Sep 25 - Sep 28
found 17 hours ago
Roundtrip flight included
Toronto (YTO) to Washington (WAS)
8.2/10 Very Good! (1,001 reviews)
Beautiful facility inside Galludet University. Allowable price and free parking in the middle of Washington DC. Thoroughly enjoyed my stay. The room was large and had many amenities. My stay was quiet and peaceful. I will definitely be back!

Reviewed on Jul. 21, 2025

Club Wyndham National Harbor

Club Wyndham National Harbor

3.5 out of 5
per person
Oct 16 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Washington (WAS)
8.4/10 Very Good! (451 reviews)
Great walkable location! In the heart of the harbor and very close to MGM. Friendly and accommodating staff

Reviewed on Jul. 4, 2025

The Watergate Hotel

The Watergate Hotel

5 out of 5
Northwest
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
8.8/10 Excellent! (1,001 reviews)
Earned its reputation

Reviewed on Jul. 24, 2025

Ready to book your vacation to Chester?

 

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Chester Hotel Deals

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 3 to Aug 4
CA $140
CA $206 total
Aug 3 - Aug 4
includes taxes & fees
8.8/10 Excellent! (1,809 reviews)
"Overall it is a great hotel to stay, close to all activities"

Reviewed on Jul. 23, 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 $212 per night from Aug 3 to Aug 4
CA $212
CA $242 total
Aug 3 - Aug 4
includes taxes & fees
9.4/10 Exceptional! (1,003 reviews)
"Excellent!"

Reviewed on Jul. 21, 2025

Graduate by Hilton Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Aug 3 to Aug 4
CA $135
CA $154 total
Aug 3 - Aug 4
includes taxes & fees
8.4/10 Very Good! (1,015 reviews)
"Beautiful property, I just wasn’t a fan of the layout. It felt like I had to walk a mile from the lobby to the elevator to get to my room. Also, one of the days of my stay there was a wedding reception. The location of my room meant that I had to walk through the reception crowd to get to the elevators ..."

Reviewed on Jul. 25, 2025

DoubleTree by Hilton Hotel Annapolis
See all 1,241 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 $489 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.