Chester Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Chester

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 2.116.611 ₫ per night from 25 Jun to 26 Jun
2.116.611 ₫
2.461.195 ₫ total
25 Jun - 26 Jun
includes taxes & fees
7.4/10 Good! (995 reviews)
"Staff was courteous and helpful."

Reviewed on 18 May 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 1.898.961 ₫ per night from 30 Jun to 1 Jul
1.898.961 ₫
2.208.112 ₫ total
30 Jun - 1 Jul
includes taxes & fees
7/10 Good! (758 reviews)
"Grateful"

Reviewed on 16 Jun 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 2.309.980 ₫ per night from 30 Jun to 1 Jul
2.309.980 ₫
2.686.045 ₫ total
30 Jun - 1 Jul
includes taxes & fees
7.2/10 Good! (1,001 reviews)
"Fine"

Reviewed on 16 Jun 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 holiday package cost?
You can snap up a holiday package to this popular destination on Expedia. However, how much your holiday 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 holiday 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 travellers wishing to save money.
How many days is enough for Chester?
With around 2 days, you'll have enough time to experience popular neighbourhoods like Bellwood and Woodvale during your Chester holiday. 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 holiday package to Chester?
It's easy to see why a Chester holiday is on the must-do list of many travellers. 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 holiday as a package?
You can enjoy significant savings on your Chester break by booking a customised holiday 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 holiday 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 favourite 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 accommodation: Once you've settled on your travel dates and duration, lock in the perfect Chester holiday package for you.

Popular places to visit

Virginia Commonwealth University

Virginia Commonwealth University

Explore the campus of Virginia Commonwealth University during your visit to Richmond. Stroll along the area's riverfront or experience its great live music.

Virginia Commonwealth University
University of Richmond

University of Richmond

5/5(1 review)

Enjoy the student vibe when you visit University of Richmond during your trip to Richmond. Attend a sporting event or simply enjoy the cosy cafes while you're in the area.

University of Richmond
Maymont Park featuring a house and heritage architecture

Maymont Park

After visiting Maymont Park, make a plan to see the other sights and activities in Richmond. Wander the picturesque gardens and riverfront in the area.

Maymont Park