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.
The Commonwealth
Downtown Richmond
CA $1,272
per person
Dec 17 - Dec 22
found 19 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Richmond (RIC)
8.8/10 Excellent! (1,407 reviews)
Water pressure in the shower was low. The sink drained very slowly. Other than that everything was great.
Reviewed on Oct 15, 2026
Kingsmill Resort
Kingsmill
CA $1,370
per person
Dec 5 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Richmond (RIC)
8.6/10 Excellent! (1,006 reviews)
Room was big (one bedroom condo) and clean. However, it needs more proper maintenance. Some lights (lamp, overhead) were burned out and have not been replaced. The toilet is not properly attached to the floor (it moves when you sit).
Reviewed on Oct 14, 2026
Ready to book your vacation to Chester?
Chester Hotel Deals
SpringHill Suites Chester
12301 REDWATER CREEK ROAD Chester VA
Fully refundableReserve now, pay when you stay
CA $171
CA $198 total
Nov 5 - Nov 6
includes taxes & fees
8.8/10 Excellent! (923 reviews)
"No Complaints Here! The room & facilities were clean. Staff was kind and inviting. Breakfast choices were plentiful. Thank You!"
Reviewed on Oct 13, 2026
Fairfield Inn By Marriott Richmond Chester
12400 Redwater Creek Rd Chester VA
Fully refundableReserve now, pay when you stay
CA $139
CA $162 total
Nov 2 - Nov 3
includes taxes & fees
8.2/10 Very good! (1,002 reviews)
"Overall good hotel very basic has what you need and always love free breakfast! (I would not recommend the handicap rooms the shower situation is crazy water gets everywhere but great water pressure lol)"
Reviewed on Oct 13, 2026
Hyatt Select Richmond/Chester
13148 Kingston Ave Chester VA
Fully refundableReserve now, pay when you stay
CA $133
CA $155 total
Nov 2 - Nov 3
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
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.
Dutch Gap Conservation Area
7.8/10 (52 reviews)
Explore the great outdoors at Dutch Gap Conservation Area, a lovely green space in Chester. Stroll along the riverfront or attend a sporting event in the area.
Parker's Battery Park
7.4/10 (38 reviews)
Explore the great outdoors at Parker's Battery Park, a lovely green space in Chester. While in this family-friendly area, you can savor the top-notch restaurants.
The Lazy Daisy
7.4/10 (39 reviews)
Enjoy an outing to The Lazy Daisy during your stay in Chester. Experience the area's live music or attend a sporting event.
Presquile National Wildlife Refuge
7.2/10 (36 reviews)
Explore the great outdoors at Presquile National Wildlife Refuge, a lovely green space in Chester. While in this family-friendly area, you can savor the top-notch restaurants.
Perkinson Center for the Arts Foundation
Enjoy an outing to Perkinson Center for the Arts Foundation during your stay in Chester. While in this family-friendly area, you can savor the top-notch restaurants.
Cultural Center of India
Enjoy an outing to Cultural Center of India during your stay in Chester. While in this family-friendly area, you can savor the top-notch restaurants.
What to do in Chester
Downtown Richmond Must-See Landmarks with Self-Guided Audio Tour
CA $14
per traveller
80% of travellers recommend
Frequently asked questions
How much does a Chester vacation package cost?
You can snap up a vacation package to this popular destination from CA $1,004 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?
- 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.
- 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.
- 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.
- 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.
