Chester Vacation Packages

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Your Chester Vacation

Reserve a Chester vacation package that includes everything you need without any unnecessary extras. Great for nightlife, cafes and festivals, consider staying in the neighborhood of Downtown Richmond. A trip to Chester is an ideal opportunity to do a bit of sightseeing. Be sure to visit well-known attractions like Iron Bridge Sports Park, Henricus Historical Park and The Lazy Daisy. A few quick clicks is all it takes to build your dream Chester vacation on Expedia.

Top Chester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Comfort Inn Petersburg Fort Lee Area

Comfort Inn Petersburg Fort Lee Area

2.5 out of 5
Price was CA $1,157, price is now CA $1,044 per person
CA $1,044
per person
Jan 24 - Jan 31
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Richmond (RIC)
8.4/10 Very good! (1,007 reviews)

Bluegreen Vacations Patrick Henry Square, an Ascend Collection Resort

Bluegreen Vacations Patrick Henry Square, an Ascend Collection Resort

3 out of 5
Price was CA $1,245, price is now CA $1,058 per person
CA $1,058
per person
Dec 17 - Dec 23
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (474 reviews)

Country Inn & Suites by Radisson, Petersburg, VA

Country Inn & Suites by Radisson, Petersburg, VA

2.5 out of 5
Price was CA $1,304, price is now CA $1,180 per person
CA $1,180
per person
Jan 24 - Jan 31
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Richmond (RIC)
8/10 Very good! (1,009 reviews)
Clean place, Cool Staff

Reviewed on Nov 6, 2026

Holiday Inn Express and Suites - Petersburg - Fort Lee by IHG

Holiday Inn Express and Suites - Petersburg - Fort Lee by IHG

2.5 out of 5
Price was CA $1,246, price is now CA $1,136 per person
CA $1,136
per person
Jan 24 - Jan 31
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Richmond (RIC)
8/10 Very good! (1,002 reviews)

Holiday Inn Express Williamsbrg Busch Gardens Area by IHG

Holiday Inn Express Williamsbrg Busch Gardens Area by IHG

2.5 out of 5
Price was CA $1,165, price is now CA $1,074 per person
CA $1,074
per person
Dec 17 - Dec 23
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9.2/10 Wonderful! (1,311 reviews)
Our stay started out on a bad note, as the young lady who checked us in was not at all pleasant nor welcoming. Not even a smile….we were tired after a long drive and a pleasant welcome would have been appreciated. The room was very clean and comfortable. We slept well. Breakfast was very nice, with many choices. All in all, a nice hotel, and we would stay again.

Reviewed on Nov 7, 2026

Ready to book your vacation to Chester?

 

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Chester Hotel Deals

SpringHill Suites Chester

SpringHill Suites Chester

2.5 out of 5
12301 REDWATER CREEK ROAD Chester VA
Fully refundableReserve now, pay when you stay
The price is CA $172 per night from Dec 6 to Dec 7
CA $172
CA $200 total
Dec 6 - Dec 7
includes taxes & fees
SpringHill Suites Chester
Fairfield Inn By Marriott Richmond Chester

Fairfield Inn By Marriott Richmond Chester

3 out of 5
12400 Redwater Creek Rd Chester VA
Fully refundableReserve now, pay when you stay
The price is CA $150 per night from Nov 30 to Dec 1
CA $150
CA $175 total
Nov 30 - Dec 1
includes taxes & fees
8.4/10 Very good! (1,002 reviews)
"Cool"

Reviewed on Nov 7, 2026

Fairfield Inn By Marriott Richmond Chester
Hyatt Select Richmond/Chester

Hyatt Select Richmond/Chester

3 out of 5
13148 Kingston Ave Chester VA
Fully refundableReserve now, pay when you stay
The price is CA $166 per night from Nov 9 to Nov 10
CA $166
CA $193 total
Nov 9 - Nov 10
includes taxes & fees
8.4/10 Very good! (1,011 reviews)
"Easy access quite breakfast was blah"

Reviewed on Nov 5, 2026

Hyatt Select Richmond/Chester
See all 1,048 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
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Stay near popular Chester attractions

Henricus Historical Park

8.0/10 (63 reviews)
Explore the great outdoors at Henricus Historical Park, a lovely green space in Chester. You can attend a sporting event while in the area.
See properties

What to do in Chester

Historic Trolley Tour

Historic Trolley Tour

CA $64
per adult
100% of travellers recommend
Historic Trolley Tour
Down in the Shokoe Bottom, the most haunted neighborhood with 350+ years of history and hauntings!

The Haunted History of Richmond tour

CA $42
per adult
The Haunted History of Richmond tour
See all activities in Chester

Frequently asked questions

How much does a Chester vacation package cost?
You can snap up a vacation package to this popular destination from CA $1,044 on Expedia. But how much your vacation to Chester costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Chester?
If you'd like to snag a cheap Chester vacation package, consider travelling in November, December and January. You'll generally find better prices on accommodations and flights during these months — perfect for travellers wishing to save money.
How many days is enough for Chester?
Chester vacations can be short or long, but to really get a feel for this destination, we'd suggest 2 days is a good ballpark. This will mean you can fit in top attractions like The Lazy Daisy and Parker's Battery Park along with hidden gems. Don't forget to explore cool areas such as Bellwood and Woodvale either. If you're smart with your time, you can even schedule a day trip from Chester too.
Is it worth booking a vacation package to Chester?
Chester is a good vacation destination with attractions like Iron Bridge Sports Park among the many things to keep you busy. Whether you're travelling with the family or getting away with friends, a Chester vacation promises a good time for everyone.
How to find the best Chester package deals?
Finding a cheap Chester package deal is a cinch with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your maximum budget, apply a couple of filters and browse what's available. You can tweak your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most economical Chester package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are typically lower.
Is it cheaper to book a Chester vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking stays and flights separately. Better still, you can tailor your Chester trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Chester?
Score incredible bargains by booking your flights in advance with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for a spur-of-the-moment Chester adventure.
How to plan a trip to Chester?

  1. Choose when to get away: Check your calendar and pack your bags. Your preferred time of year and the activities on offer will also help you decide when to vacation in Chester.
  2. Set your budget: Consider expenses such as flights, food and transportation when calculating how much to set aside for your trip to Chester. Then, select a hotel that matches your budget, whether that's a wallet-friendly stay or a deluxe retreat.
  3. Decide how long to go for: Now that you're more familiar with Chester, you can work out the right length of your break. Pull together a draft plan and allocate enough time for all the things you want to do.
  4. Bundle your accommodations and airfare: Once you've settled on your trip dates and duration, book the right Chester vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.