Chester Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Choose two or more items and save on your trip:
    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to CA $775 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

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.
Fort Magruder Historic Williamsburg, Trademark by Wyndham

Fort Magruder Historic Williamsburg, Trademark by Wyndham

3.5 out of 5
per person
Aug. 2 - Aug. 9
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Richmond (RIC)
7.2/10 Good! (1,132 reviews)
The main areas were clean and overall attractive. Nice pool and beautiful Courtyard. The rooms and always had really old, nasty carpet. The walls in the room were red and beige. Just needs a simple update with new paint in a light neutral color and new carpet. In our room there did not seem to be any padding under the carpet and the floor felt uneven. I did not want to walk on it with bear feet, it was so dirty looking. The breakfast was nice because it was a big space and had lots of options including hot food and fresh waffles.

Reviewed on Jun. 13, 2024

Westgate Historic Williamsburg Resort

Westgate Historic Williamsburg Resort

3.5 out of 5
per person
Aug. 2 - Aug. 9
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Richmond (RIC)
8.2/10 Very Good! (1,005 reviews)
rooms are very small

Reviewed on Jun. 13, 2024

Williamsburg Inn, an official Colonial Williamsburg Hotel

Williamsburg Inn, an official Colonial Williamsburg Hotel

5 out of 5
per person
Aug. 2 - Aug. 9
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Richmond (RIC)
9.8/10 Exceptional! (180 reviews)
Your property is wonderful. Felt like royalty. The room was exquisite. The extra touch’s and live flowers were enchanting. I couldn’t give you high enough praise. Well done Williamsburg Inn.

Reviewed on Jun. 10, 2024

Club Wyndham Governor’s Green

Club Wyndham Governor’s Green

3 out of 5
per person
Aug. 2 - Aug. 9
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Richmond (RIC)
9/10 Wonderful! (146 reviews)
Very nice property. Our suite was nice but dated. Could use more modern design and furnishings.

Reviewed on Jun. 7, 2024

DoubleTree by Hilton Williamsburg

DoubleTree by Hilton Williamsburg

4 out of 5
per person
Aug. 2 - Aug. 9
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Richmond (RIC)
8/10 Very Good! (1,006 reviews)
Bathroom doors need yo be replace or fix they all rubb.

Reviewed on Jun. 14, 2024

Chester Hotel Deals

SpringHill Suites Chester
SpringHill Suites Chester
2.5 out of 5
12301 REDWATER CREEK ROAD, Chester, VA
Fully refundableReserve now, pay when you stay
The price is CA $181 per night from Jun. 23 to Jun. 24
CA $181
CA $211 total
includes taxes & fees
Jun 23 - Jun 24
9/10 Wonderful! (339 reviews)
"This hotel was comfortable and clean. It was conveniently located just off the exit and had several food options close by."

Reviewed on Jun. 14, 2024

SpringHill Suites 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 $139 per night from Jul. 7 to Jul. 8
CA $139
CA $162 total
includes taxes & fees
Jul 7 - Jul 8
6.8/10 (1,003 reviews)
It was an ok stay
"Need better cleaning methods vents had black dust walls had spots that should have been wiped no complimentary bottles of water comfortable bed suite was semi spacious"

Reviewed on Jun. 14, 2024

Country Inn & Suites by Radisson, Chester, VA
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 $102 per night from Jun. 19 to Jun. 20
CA $102
CA $119 total
includes taxes & fees
Jun 19 - Jun 20
6.8/10 (521 reviews)
"It was ok."

Reviewed on Jun. 14, 2024

Red Roof Inn Chester
See all 844 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

Frequently asked questions

How much does a Chester vacation package cost?
Customize your Chester vacation package from only CA $1,430. Pick from any combination of flights, hotels and rental cars to build the getaway you’ve been dreaming of. Don’t forget to add on some tours and experiences!
How do I get a cheap travel package to Chester?
Booking a Chester vacation package with Expedia is one of the best ways to save. We offer access to over 550 partner airlines and 1,000,000 hotels throughout the world. With such a fantastic range to choose from, you’ll have no hassles creating your next dream getaway.
Where should I stay in Chester?
With so much to discover in Chester, we recommend you stay near its attractions. Iron Bridge Sports Park, The Lazy Daisy and Dutch Gap Conservation Area are some popular ones to put on your must-see list.
What are the top hotels in Chester?
Country Inn & Suites by Radisson, Chester, VA will make an excellent base for your Chester adventures. Located in Woodvale, it’s one of this area’s most sought-after hotels.
How far in advance should I book my Chester vacation?
While prices fluctuate, we generally suggest booking your seats as early as possible. Many international fares become available on Expedia up to 12 months in advance. If you’re booking last minute, you might still be in luck. Cheap tickets to Chester sometimes emerge in the weeks prior to departure.
What does an Expedia Chester travel package include?
From hotels and airfares to rental cars, Expedia can help you put together a Chester package that fits you. Vacationing for a week or longer? Give some thought to a rental car, flight and hotel bundle. If you can only squeeze in a quick getaway, an airfare and hotel deal could be what you’re after. Activities can also be added after you’ve booked. Our packages make it easy to plan and save.
What should I know before booking a Chester travel package?
You can look forward to saving with an Expedia travel package. Combine your airfares, rental cars and hotels and be rewarded with terrific discounts. You’re not limited to hotels, however. We have beachfront villas, cabins in the mountains and just about everything in between!
Can I choose my airline with a Chester Expedia vacation package?
Yes, definitely. Expedia has over 550 airline partners to choose from worldwide. With all that choice, finding the perfect carrier to whisk you away to Chester shouldn’t be hard.
If I'm not able to travel, can I cancel my Chester vacation package?
It is possible to cancel your Chester booking if your travel plans have been upended. Whether you’ll be charged a fee or not depends on your hotel, airline or car rental company. It may be possible to cancel or change for free if you booked in the last 24 hours. Head to our Customer Service Portal to find out more.

Discover the most popular places to visit in Chester

Image for Virginia Commonwealth University

Virginia Commonwealth University

4.5/5(7 reviews)

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

Virginia Commonwealth University
Image for Broad Street

Broad Street

4/5(8 reviews)

During your trip to Richmond, you can find the perfect gifts to bring home at Broad Street. While you're here, you can savor the top-notch restaurants.

Broad Street
Image for University of Richmond

University of Richmond

Take a campus tour or just explore the area of University of Richmond, during your trip to Richmond. Attend a sporting event or simply enjoy the charming coffeehouses while you're in the area.

University of Richmond

What to do in Chester

Image for Richmond's Street Art Segway Tour

Richmond's Street Art Segway Tour

CA $103
Per adult
Richmond's Street Art Segway Tour
Image for Would I Lie To You? Mural Walks

Would I Lie To You? Mural Walks

CA $27
Per adult
Would I Lie To You? Mural Walks
Image for Phantoms of Franklin Ghost Tour

Phantoms of Franklin Ghost Tour

CA $41
Per adult
Phantoms of Franklin Ghost Tour
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.