Chester Vacation Rentals

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Check prices for these dates

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

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
The price is AED 441
AED 1,271 total
includes taxes & fees
15 Nov - 16 Nov
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.
The price is AED 305
AED 1,243 total
includes taxes & fees
15 Nov - 16 Nov
Game Room + Yard: Updated House in Chester!
A marina with docked boats, a covered structure, and a forested hillside in the background.

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, (252 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.
The price is AED 422
AED 751 total
includes taxes & fees
9 Nov - 10 Nov
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
A grand lobby with a large Christmas tree, marble columns, and a red carpeted floor.

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.
The price is AED 422
AED 751 total
includes taxes & fees
9 Nov - 10 Nov
A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations
A dock with a boat, a wooden pier, and a house with a red roof in the background.

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
The price is AED 784
AED 1,019 total
includes taxes & fees
9 Nov - 10 Nov
MV GiaMaria
A dock area with boats, a covered seating area, and a sign indicating no trespassing for boat owners and guests only.

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
The price is AED 803
AED 1,100 total
includes taxes & fees
9 Nov - 10 Nov
Cookie B
A hotel room with two beds, a desk, a chair, a television, and a window with curtains.

7. 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
The price is AED 253
AED 278 total
includes taxes & fees
12 Nov - 13 Nov
2 Queen Beds | Non-Smoking, Micfridge
A wooden deck with a table and chairs, surrounded by potted plants and a wooden fence.

8. 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.
The price is AED 404
AED 846 total
includes taxes & fees
15 Nov - 16 Nov
Newly finished basement suite in Midlothian. Very clean and spacious.
A room with a fireplace, a mirror above it, and two leather chairs.

9. 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.
The price is AED 272
AED 509 total
includes taxes & fees
30 Nov - 1 Dec
Nest & Rest | Private Studio | Free Parking
A corner building with large windows and a black awning.

10. 402 Heart of the Arts in Downtown RVA near MCV VCU Convention Center

402 Heart of the Arts in Downtown RVA near MCV VCU Convention Center
Downtown Richmond
9.4 out of 10, Exceptional, (19 reviews)
"The building is right on a bus line, and was an easy to walk to various locations in the city as well as lots of restaurants."
United States
Jeffrey O.
402 Heart of the Arts in Downtown RVA near MCV VCU Convention Center
A corner building with large windows and a black awning.

11. Heart of RVA Arts District Walk to VCU, MCV, The National, Quirk Prime Downtown

Heart of RVA Arts District Walk to VCU, MCV, The National, Quirk Prime Downtown
Downtown Richmond
9.6 out of 10, Exceptional, (27 reviews)
"Great location, reasonable rates for the area, friendly helpful staff. Would stay here again."
United States
George L.
The price is AED 264
AED 604 total
includes taxes & fees
9 Nov - 10 Nov
Heart of RVA Arts District Walk to VCU, MCV, The National, Quirk Prime Downtown
A spacious restaurant with high ceilings, large windows, and a central bar area.

12. 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
The price is AED 268
AED 608 total
includes taxes & fees
9 Nov - 10 Nov
Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!
A living room with a sofa, coffee table, TV, and a door with a 'No Smoking' sign.

13. 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.
The price is AED 366
AED 727 total
includes taxes & fees
25 Nov - 26 Nov
The Birdhouse - Cozy Cottage Retreat in Richmond
A bedroom with a bed, a TV, and built-in shelving with decorative items.

14. 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.
The price is AED 238
AED 406 total
includes taxes & fees
9 Nov - 10 Nov
Magnolias, a chill out place.
A room with a large window overlooking a cityscape.

15. 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
The price is AED 215
AED 296 total
includes taxes & fees
23 Nov - 24 Nov
Cozy studio apartment in tranquil Richmond with heat and gym access
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.

16. 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
The price is AED 169
AED 223 total
includes taxes & fees
9 Nov - 10 Nov
2 Full Beds|Non-Smoking
A hotel room with two beds, a window with a view of parked cars, a wooden headboard, and a framed picture on the wall.

17. 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
The price is AED 169
AED 223 total
includes taxes & fees
9 Nov - 10 Nov
2 Full Bed|Smoking|Petersburg VA
A gray sectional sofa with patterned cushions, a white door, decorative wall art, a window with blinds, and a small table with a lamp.

18. 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.
The price is AED 382
AED 700 total
includes taxes & fees
11 Nov - 12 Nov
The Fan Comfort Stay near VCU Free Parking Fenced Yard
A rural landscape with a dirt path, grassy areas, and a building with a green roof.

19. 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.
The price is AED 413
AED 932 total
includes taxes & fees
11 Nov - 12 Nov
Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.
A high-ceilinged interior with skylights and built-in shelving.

20. Heart of the Arts - New King Suite on West Broad Condo’s next to Quirk MCV VCU

Heart of the Arts - New King Suite on West Broad Condo’s next to Quirk MCV VCU
Downtown Richmond
9.8 out of 10, Exceptional, (61 reviews)
"Great stay."
United States
Brian D.
Heart of the Arts - New King Suite on West Broad Condo’s next to Quirk MCV VCU
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

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.