Chester Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Chester vacation rentals

A spacious living area with a high ceiling, a staircase, and a dining area with modern furniture.

1. Game Room + Yard: Updated House in Chester!

Game Room + Yard: Updated House in Chester!
3.0 star property
Chester
$304 nightly
The price is $346
Nov 15 - Nov 16
Total with taxes and fees
Game Room + Yard: Updated House in Chester!
A spacious living area with a high ceiling, a staircase, and a dining area with modern furniture.

2. Game Room + Yard: Updated House in Chester!

Game Room + Yard: Updated House in Chester!
Chester
9.0 out of 10, Wonderful, (4 reviews)
"Great stay. Super clean! Great communication with host. 30 mins from Richmond VA, great for exploring surrounding areas!"
United States
Akia S.
$294 nightly
The price is $338
Nov 15 - Nov 16
Total with taxes and fees
Game Room + Yard: Updated House in Chester!
A compact living area with a blue sofa, a purple armchair, and a small table with a checkered edge.

3. A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city

A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
Richmond
9.4 out of 10, Exceptional, (251 reviews)
"We had a great stay! Perfect get away for our anniversary. It had everything we needed and was super quiet with a great view. Thank you Captain Ron, for an amazing experience "
United States
Allison K.
$178 nightly
The price is $203
Nov 8 - Nov 9
Total with taxes and fees
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
A cozy living room with a television, a fireplace, a Coca-Cola branded stool, and a patterned rug.

4. A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations

A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations
Richmond
9.6 out of 10, Exceptional, (126 reviews)
"Great alternative to a house or hotel"
United States
Ashley Jo P.
$178 nightly
The price is $203
Nov 8 - Nov 9
Total with taxes and fees
A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations
A calm lake with a dock and a small building, surrounded by trees.

5. MV GiaMaria

MV GiaMaria
3.5 star property
Richmond
9.4 out of 10, Exceptional, (16 reviews)
"So much fun!! Excellent host! Very informative. Loved the privacy and being on the water. The bed was super comfortable and the fireplace (electric) kept us warm and cozy. It was such a unique thing to do and we will be back!"
United States
Jane
$243 nightly
The price is $277
Nov 6 - Nov 7
Total with taxes and fees
MV GiaMaria
A boat with a cabin, a small deck area with a ramp, and a docked boat in the background.

6. Cookie B

Cookie B
3.0 star property
Richmond
9.2 out of 10, Wonderful, (10 reviews)
"Was fantastic. Watching the sunrise was so memorable, captain ron was so friendly and stayed in communication well. will visit again. "
United States
Reshelle
$263 nightly
The price is $299
Nov 6 - Nov 7
Total with taxes and fees
Cookie B
A living room with a sofa, coffee table, TV, and a door with a 'No Smoking' sign.

7. The Birdhouse - Cozy Cottage Retreat in Richmond

The Birdhouse - Cozy Cottage Retreat in Richmond
Swansboro West
10.0 out of 10, Exceptional, (6 reviews)
"The BirdHouse is such a comfortable place. We loved the uniqueness and the little touches that mean alot on the road. We hope to stay again sometime."
United States
paula S.
$196 nightly
The price is $198
Nov 15 - Nov 16
Total with taxes and fees
The Birdhouse - Cozy Cottage Retreat in Richmond
A hotel room with two beds, a desk, a chair, a television, and a window with curtains.

8. 2 Queen Beds | Non-Smoking, Micfridge

2 Queen Beds | Non-Smoking, Micfridge
Petersburg VA
10.0 out of 10, Exceptional, (4 reviews)
"Clean rooms with quick service!"
United States
Anonymous traveler
$69 nightly
The price is $76
Nov 10 - Nov 11
Total with taxes and fees
2 Queen Beds | Non-Smoking, Micfridge
A wooden deck with a table and chairs, surrounded by potted plants and a wooden fence.

9. Newly finished basement suite in Midlothian. Very clean and spacious.

Newly finished basement suite in Midlothian. Very clean and spacious.
Midlothian
10.0 out of 10, Exceptional, (6 reviews)
"Cute place. Very spacious and clean. Great communication. Would definitely stay again. Thank you!"
United States
Jeannie C.
$200 nightly
The price is $230
Nov 12 - Nov 13
Total with taxes and fees
Newly finished basement suite in Midlothian. Very clean and spacious.
A room with a fireplace, a mirror above it, and two leather chairs.

10. Nest & Rest | Private Studio | Free Parking

Nest & Rest | Private Studio | Free Parking
Fan District
9.8 out of 10, Exceptional, (46 reviews)
"Host was gracious and responsive, and the location was amazing! "
United States
Kelly M.
$116 nightly
The price is $128
Dec 2 - Dec 3
Total with taxes and fees
Nest & Rest | Private Studio | Free Parking
A corner building with large windows and a black awning.

11. City Arts District in Downtown VCU MCV

City Arts District in Downtown VCU MCV
Downtown Richmond
9.8 out of 10, Exceptional, (33 reviews)
"Great place to stay! Walkable shops around. Will definitely stay here again."
United States
Yvonne V.
City Arts District in Downtown VCU MCV
A rural landscape with a pond, grassy fields, and trees under a cloudy sky.

12. Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.

Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.
Chesterfield
10.0 out of 10, Exceptional, (7 reviews)
"Quiet and Cozy. Beautiful scenery, great walking trails. Host was extra accomdating with check-in and out process. Would definitely visit again "
United States
G H.
$221 nightly
The price is $254
Nov 11 - Nov 12
Total with taxes and fees
Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.
A bedroom with a bed, a TV, and built-in shelving with decorative items.

13. Magnolias, a chill out place.

Magnolias, a chill out place.
Richmond
9.2 out of 10, Wonderful, (25 reviews)
"Would stay again!"
United States
Amir D.
$97 nightly
The price is $111
Nov 9 - Nov 10
Total with taxes and fees
Magnolias, a chill out place.
A room with a sofa, a coffee table, a dining table with chairs, a window with a 'Thank You' sign, and a view of trees.

14. 2 Full Beds|Non-Smoking

2 Full Beds|Non-Smoking
Petersburg VA
10.0 out of 10, Exceptional, (81 reviews)
"Appreciated the cozy lounge area, made relaxing after a long day easy."
United States
Anonymous traveler
$53 nightly
The price is $60
Nov 6 - Nov 7
Total with taxes and fees
2 Full Beds|Non-Smoking
A gray sectional sofa with patterned cushions, a white door, decorative wall art, a window with blinds, and a small table with a lamp.

15. The Fan Comfort Stay near VCU Free Parking Fenced Yard

The Fan Comfort Stay near VCU Free Parking Fenced Yard
Fan District
9.6 out of 10, Exceptional, (32 reviews)
"Very convenient location, and great communication!"
United States
Katelyn F.
$172 nightly
The price is $190
Nov 8 - Nov 9
Total with taxes and fees
The Fan Comfort Stay near VCU Free Parking Fenced Yard
A modern kitchen with a central island, a dining area with a sofa and coffee table, and large windows offering a view.

16. Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!

Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!
Downtown Richmond
9.8 out of 10, Exceptional, (93 reviews)
"Just a great space to stay very comfortable and the location is awesome - many nearby clubs bars and places to eat! Have stayed 4 times and one of my favorite places to stay anywhere"
United States
rob
$163 nightly
The price is $186
Nov 9 - Nov 10
Total with taxes and fees
Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!
A room with a large window overlooking a cityscape.

17. Cozy studio apartment in tranquil Richmond with heat and gym access

Cozy studio apartment in tranquil Richmond with heat and gym access
Downtown Richmond
8.8 out of 10, Excellent, (9 reviews)
"Clean environment. Great views. Very little parking flexibility but an enjoyable walk."
United States
Cailyn
$80 nightly
The price is $91
Nov 22 - Nov 23
Total with taxes and fees
Cozy studio apartment in tranquil Richmond with heat and gym access
A modern kitchen with stainless steel appliances, a white countertop, and pendant lighting.

18. Downtown Living in Richmond's Amazing Shockoe Bottom

Downtown Living in Richmond's Amazing Shockoe Bottom
Downtown Richmond
8.6 out of 10, Excellent, (36 reviews)
"Was I great place to stay! Very responsive and gave all the info you need to make the trip and stay easy! "
United States
Dillon D.
$291 nightly
The price is $310
Nov 9 - Nov 10
Total with taxes and fees
Downtown Living in Richmond's Amazing Shockoe Bottom
A hotel room with two beds, a window with a view of parked cars, a wooden headboard, and a framed picture on the wall.

19. 2 Full Bed|Smoking|Petersburg VA

2 Full Bed|Smoking|Petersburg VA
Petersburg VA
10.0 out of 10, Exceptional, (81 reviews)
"Cozy spot with friendly staff."
United States
Anonymous traveler
$53 nightly
The price is $60
Nov 6 - Nov 7
Total with taxes and fees
2 Full Bed|Smoking|Petersburg VA
A reception desk with a computer, a telephone, and a small plant.

20. 1 King Bed | Non-Smoking, Micfridge

1 King Bed | Non-Smoking, Micfridge
Petersburg VA
10.0 out of 10, Exceptional, (3 reviews)
"Rooms felt fresh and cozy with everything just right."
United States
Anonymous traveler
$71 nightly
The price is $78
Nov 10 - Nov 11
Total with taxes and fees
1 King Bed | Non-Smoking, Micfridge
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.
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Top Chester Hotel Reviews

A modern hotel with multiple buildings, including a section labeled 'Home Suites by Hilton.'
Home2 Suites by Hilton Richmond Chester

Home2 Suites by Hilton Richmond Chester

Home2 Suites by Hilton Richmond Chester
Chester

10/10 Excellent

A little pricey but clean and had a good breakfast. Good For a 1 night stay
United States
William
Reviewed November 2, 2026
Home2 Suites by Hilton Richmond Chester

Find out more about Chester

Everything you need to know about Chester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $60 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find vacation rentals in Chester?

Yes, there are vacation rentals in Chester close to Iron Bridge Sports Park, or you can select a more secluded option if you want a relaxing stay. Visitors like the top-notch restaurants and shops in Chester. Make sure you have time to check out the art and cafes during your trip.

What's the top vacation rental in Chester?

Spacious 4-bedroom house in awesome Midlothian with AC: This vacation home rental outside of Chester offers a fireplace, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave.

How many vacation rentals are there in Chester?

With 8 Expedia vacation rentals, you're sure to find just the right place for your Chester stay.

What’s there to see and do in Chester?

Family-friendly attractions include Iron Bridge Sports Park and The Lazy Daisy, whereas James River and Henricus Historical Park are a couple of great spots to enjoy the outdoors. Dutch Gap Conservation Area and Point of Rocks Park are other places to visit while you're in town.

What’s a vacation rental in Chester like?

A vacation rental is a private property you can book for several days or longer in Chester. Vacation rentals feature amenities such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, a vacation rental can provide a sense of safety away from shared hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for small groups.

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