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 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.
Wingate by Wyndham Richmond Short Pump
Short Pump
Price was CA $1,485, price is now CA $1,115 per person
CA $1,115
per person
Jul 23 - Jul 30
found 23 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Richmond (RIC)
8.4/10 Very Good! (1,833 reviews)
There was no accommodation for disabled or handicapped visitors the toilet was very not even a toilet helper to help no handicapped rails in bathroom my sister had knee and hip surgery and I requested a handicapped room and breakfast was fair no fruit only green apples I will not be staying at this hotel again Hilton was next door same price I do visit short pump twice a year for shopping was planning a ladies fellowship next year will not be using this hotel
Reviewed on May 6, 2026
Kingsmill Resort
Kingsmill
Price was CA $2,081, price is now CA $1,517 per person
CA $1,517
per person
Jul 23 - Jul 30
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Richmond (RIC)
8.8/10 Excellent! (1,004 reviews)
You could have told us before we booked (indeed, even before we checked in!) that the main restaurant and the spa (the two amenities we looked forward to) weren’t open for the first two days of our three-day stay.
Reviewed on May 8, 2026
Graduate by Hilton Richmond
Downtown Richmond
Price was CA $1,661, price is now CA $1,279 per person
CA $1,279
per person
Jul 23 - Jul 30
found 23 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Richmond (RIC)
8.4/10 Very Good! (1,369 reviews)
Nice location just north of downtown, close to VCU. Excellent bar and restaurant.
Reviewed on May 8, 2026
Hilton Richmond Hotel & Spa/Short Pump
Short Pump
Price was CA $1,689, price is now CA $1,300 per person
CA $1,300
per person
Jul 23 - Jul 30
found 23 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Richmond (RIC)
8.8/10 Excellent! (1,003 reviews)
Room was clean, property was quiet, and staff was friendly and helpful
Reviewed on May 3, 2026
Chester Hotel Deals
SpringHill Suites Chester
12301 REDWATER CREEK ROAD Chester VA
Fully refundableReserve now, pay when you stay
The price is CA $164 per night from May 21 to May 22
CA $164
CA $191 total
May 21 - May 22
includes taxes & fees
8.8/10 Excellent! (787 reviews)
The elevator is very slow and the room was small the room was weird the tv at the edge of the room which didn’t make sense to me and the bathroom door did not close you had to put a shoe to keep it close .. breaks fast was good
Reviewed on May 7, 2026
Suburban Studios Chester
2403 W Hundred Rd Chester VA
Fully refundableReserve now, pay when you stay
The price is CA $87 per night from Jun 8 to Jun 9
CA $87
CA $101 total
Jun 8 - Jun 9
includes taxes & fees
8/10 Very Good! (545 reviews)
Garbage everywhere. Carpet in the halls were filthy. Bathtub had hole in it. Water was lukewarm.
Reviewed on May 5, 2026
Fairfield Inn By Marriott Richmond Chester
12400 Redwater Creek Rd Chester VA
Fully refundableReserve now, pay when you stay
The price is CA $146 per night from May 12 to May 13
CA $146
CA $173 total
May 12 - May 13
includes taxes & fees
8.2/10 Very Good! (933 reviews)
Good
Reviewed on May 8, 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.
Discover the most popular places to visit in Chester
Maymont Park
This grand estate is a family favorite with a petting zoo, native wildlife and a preserved 19th-century mansion.
Virginia Museum of Fine Arts
This museum houses Russian jewels, impressionist masters and ancient relics in its vast and varied collection.
Lewis Ginter Botanical Garden
Spend some time admiring the beautiful and diverse floral displays featured in this superb botanical garden, one of the finest in the country.
What to do in Chester
Richmond Ghost Tour: Sinister Secrets of Shockoe Bottom
CA $44
per adult
88% of travellers recommend
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
