Chester Vacations

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Find the Best Chester Vacation Packages

Chester Hotel Deals

Comfort Inn Chester - Richmond South
Comfort Inn Chester - Richmond South
2.5 out of 5
2100 W Hundred Rd, Chester, VA
Fully refundableReserve now, pay when you stay
The price is ￥11,785 per night from Jun 24 to Jun 25
￥11,785
￥13,703 total
Jun 24 - Jun 25
includes taxes & fees
7.4/10 Good! (995 reviews)
"Staff was courteous and helpful."

Reviewed on May 18, 2025

Comfort Inn Chester - Richmond South
Red Roof Inn Chester
Red Roof Inn Chester
2 out of 5
2405 W Hundred Rd, Chester, VA
Fully refundableReserve now, pay when you stay
The price is ￥10,573 per night from Jun 23 to Jun 24
￥10,573
￥12,295 total
Jun 23 - Jun 24
includes taxes & fees
7/10 Good! (758 reviews)
"Grateful"

Reviewed on Jun 16, 2025

Red Roof Inn Chester
Country Inn & Suites by Radisson, Chester, VA
Country Inn & Suites by Radisson, Chester, VA
3 out of 5
2406 W Hundred Rd, Chester, VA
Fully refundable
The price is ￥12,861 per night from Jun 29 to Jun 30
￥12,861
￥14,954 total
Jun 29 - Jun 30
includes taxes & fees
7.2/10 Good! (1,000 reviews)
"Fine"

Reviewed on Jun 16, 2025

Country Inn & Suites by Radisson, Chester, VA
See all 908 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.

Frequently asked questions

How much does a Chester vacation package cost?
You can snap up a vacation package to this popular destination on Expedia. However, how much your vacation to Chester costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Chester?
If you're looking to snag a cheap Chester vacation package, consider planning a trip in November, December and January. You're likely to find lower rates on hotels and airfares during these months --- perfect for travelers wishing to save money.
How many days is enough for Chester?
With around 2 days, you'll have enough time to experience popular neighborhoods like Bellwood and Woodvale during your Chester vacation. Be sure to also add Dutch Gap Conservation Area and Henricus Historical Park to your must-do list. Searching for more adventures? Consider venturing outside of Chester on tours and day trips.
Is it worth booking a vacation package to Chester?
It's easy to see why a Chester vacation is on the must-do list of many travelers. Major attractions like Iron Bridge Sports Park are just the beginning of things to see and do here.
How to find the best Chester package deals?
Bagging a cheap Chester package deal is a cinch with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your budget, apply a couple of filters and browse what's available. You can fine-tune your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Chester package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Chester vacation as a package?
You can enjoy significant savings on your Chester break 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 great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Chester?
Enjoy incredible bargains by reserving your flights early with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for an impromptu Chester getaway.
How to plan a trip to Chester?

  1. Pick your travel dates: The things you plan to do in Chester and your favorite season will help you decide when to travel.
  2. Set your budget: Factor in expenses like flights, transportation and food when working out how much to put aside for your trip to Chester. Then, choose a property that works with your budget, whether that's an economical option or a high-end retreat.
  3. Work out your trip length: Consider how long you want to spend exploring Chester. Plan your days so you can get to all the attractions and experiences you're interested in at a comfortable pace.
  4. Bundle your airfare and accommodations: Once you've settled on your travel dates and duration, lock in the perfect Chester vacation package for you.

Discover the most popular places to visit in Chester

Maymont Park which includes heritage architecture and a house

Maymont Park

4.5/5(86 reviews)

This grand estate is a family favorite with a petting zoo, native wildlife and a preserved 19th-century mansion.

Maymont Park
Virginia Museum of Fine Arts featuring a city and art

Virginia Museum of Fine Arts

4.5/5(317 reviews)

This museum houses Russian jewels, impressionist masters and ancient relics in its vast and varied collection.

Virginia Museum of Fine Arts
Altria Theater

Altria Theater

4.5/5(79 reviews)

Enjoy a performance at Altria Theater, a storied theater in Richmond. Amble around the area's picturesque gardens or attend a sporting event.

Altria Theater

What to do in Chester

Historic Trolley Tour

Historic Trolley Tour

￥6,073
per adult
Historic Trolley Tour
Richmond: Guided Hike in James River Park

Richmond: Guided Hike in James River Park

￥4,193
per adult
Richmond: Guided Hike in James River Park
“Our guide was awesome, kind and very knowledgeable about the area and each restaurant. I highly recommend this company and we will be taking the other tours they offer.” - River City Food Tours guest

Arts District Food Tour in Richmond with Discover Richmond

￥13,592
per adult
Arts District Food Tour in Richmond with Discover Richmond
See all activities in Chester
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.