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.
A house full of steel balls and games

A house full of steel balls and games

2.5 out of 5
Dumbarton
per person
Oct 16 - Oct 19
found 1 hour ago
Roundtrip non-stop flight included
Montreal (YUL) to Richmond (RIC)
9.6/10 Exceptional! (92 reviews)
Great place to stay. Pete is a great host, easy check in great communication, pinball machines and games in the rooms really great. Quick drive to some good dining.

Reviewed on Jun. 10, 2025

The Colonies at Williamsburg

The Colonies at Williamsburg

3 out of 5
per person
Aug 23 - Aug 30
found 7 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Richmond (RIC)
9/10 Wonderful! (1,010 reviews)
Loved everything staff, property, pools, room, and rates.

Reviewed on Jul. 22, 2025

Linden Row Inn

Linden Row Inn

3 out of 5
Downtown Richmond
per person
Oct 16 - Oct 19
found 1 hour ago
Roundtrip non-stop flight included
Montreal (YUL) to Richmond (RIC)
9.2/10 Wonderful! (1,070 reviews)
really clean and organized and love the style of the room

Reviewed on Jul. 22, 2025

Virginia Crossings Hotel, Tapestry Collection by Hilton

Virginia Crossings Hotel, Tapestry Collection by Hilton

3.5 out of 5
per person
Oct 16 - Oct 19
found 1 hour ago
Roundtrip non-stop flight included
Montreal (YUL) to Richmond (RIC)
8.8/10 Excellent! (1,000 reviews)
OMG The estate is huge and hidden. Beautiful and quiet area. Amazing property.

Reviewed on Jul. 18, 2025

The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
per person
Oct 16 - Oct 19
found 1 hour ago
Roundtrip non-stop flight included
Montreal (YUL) to Richmond (RIC)
8.8/10 Excellent! (1,246 reviews)
Valet was super profession, cheerful, helpful. General nice person

Reviewed on Jul. 21, 2025

Ready to book your vacation to Chester?

 

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Chester Hotel Deals

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 CA $99 per night from Jul 29 to Jul 30
CA $99
CA $116 total
Jul 29 - Jul 30
includes taxes & fees
7/10 Good! (782 reviews)
"the room a/c was set on 72 the room was at 65 couldn't get it any different brrr"

Reviewed on Jul. 20, 2025

Red Roof Inn Chester
Hyatt Place Richmond/Chester

Hyatt Place Richmond/Chester

3 out of 5
13148 Kingston Ave, Chester, VA
Fully refundableReserve now, pay when you stay
The price is CA $171 per night from Jul 23 to Jul 24
CA $171
CA $199 total
Jul 23 - Jul 24
includes taxes & fees
8.2/10 Very Good! (1,006 reviews)
"Although this property is under renovation, the staff made up for any inconveniences that might have existed. I was welcomed by a staff member every time I entered the front door. This is exceptional !"

Reviewed on Jul. 21, 2025

Hyatt Place Richmond/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 CA $121 per night from Aug 3 to Aug 4
CA $121
CA $141 total
Aug 3 - Aug 4
includes taxes & fees
7.4/10 Good! (1,003 reviews)
"It was a very good hotel. Not the best I have stayed in. But, I was pleased with it."

Reviewed on Jul. 19, 2025

Country Inn & Suites by Radisson, Chester, VA
See all 922 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

Family Vacations

Discover the most popular places to visit in Chester

Maymont Park showing a house and heritage architecture

Maymont Park

5/5(2 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 which includes art and a city

Virginia Museum of Fine Arts

4.5/5(3 reviews)

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

Virginia Museum of Fine Arts
Lewis Ginter Botanical Garden featuring a park

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.

Lewis Ginter Botanical Garden

What to do in Chester

Historic Trolley Tour

Historic Trolley Tour

CA $57
per adult
100% of travellers recommend
Historic Trolley Tour
Richmond: Guided Hike in James River Park

Richmond: Guided Hike in James River Park

CA $48
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

CA $129
per adult
Arts District Food Tour in Richmond with Discover Richmond
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 $516 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.