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.
Warner Hall

Warner Hall

3 out of 5
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Richmond (RIC)
10/10 Exceptional! (9 reviews)
We had a wonderful, relaxing weekend stay at Warner Hall. The hosts Christina and Fred were very welcoming and the house and property is amazing. The house (more like mansion) and rooms are huge and comfortable with lots of space for reading a book, etc. We really enjoyed the morning coffee and tea service brought straight to our rooms. We felt like royalty! There's so much history to the Warners, we had no idea. Definitely highly recommend this place if you're looking for a break from being busy busy.

Reviewed on Jul. 9, 2025

Hilton Richmond Downtown

Hilton Richmond Downtown

4 out of 5
Downtown Richmond
per person
Sep 28 - Oct 4
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.4/10 Very Good! (1,008 reviews)
Jason on front desk was very nice and gave us an upgraded room, which was very spacious! And beds were so comfortable!! Only complaint was they charged me for parking, when I didn’t even drive. But front desk fixed and removed from my bill.

Reviewed on Jul. 21, 2025

Hilton Richmond Hotel & Spa/Short Pump

Hilton Richmond Hotel & Spa/Short Pump

4 out of 5
Short Pump
per person
Sep 28 - Oct 4
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
8.8/10 Excellent! (1,002 reviews)
We've stayed in this hotel many times over the years and I've always been satisfied. This time we were very disappointed that they now charge for parking at the hotel. The price of the hotel per night is a little steep so we feel like it was just another way for them to pinch off more money. We will not be staying there again, too many nice places right around the same hotel that do not charge for parking.

Reviewed on Jul. 23, 2025

The Commonwealth

The Commonwealth

4 out of 5
Downtown Richmond
per person
Oct 2 - Oct 5
found 16 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Richmond (RIC)
8.8/10 Excellent! (1,246 reviews)
The building has a lot of character both inside and outside. The suite we stayed in was large and was decorated in an eclectic style.

Reviewed on Jul. 23, 2025

Quirk Hotel Richmond

Quirk Hotel Richmond

4 out of 5
Downtown Richmond
per person
Sep 28 - Oct 4
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Richmond (RIC)
9/10 Wonderful! (1,000 reviews)
plenty of dining options in walking distance, fun bar, cool gallery, great views from the rooftop

Reviewed on Jul. 22, 2025

Ready to book your vacation to Chester?

 

Choose your dates

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 27 to Jul 28
CA $99
CA $115 total
Jul 27 - Jul 28
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 $165 per night from Jul 27 to Jul 28
CA $165
CA $191 total
Jul 27 - Jul 28
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 $140 total
Aug 3 - Aug 4
includes taxes & fees
7.4/10 Good! (1,005 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

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

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 $1,150 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.