Lodging Image

Chester Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Chester vacation rentals

View from property

1. MV GiaMaria

MV GiaMaria
3.5 star property
Richmond
9.2 out of 10, Wonderful, (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
24 Sep - 25 Sep
MV GiaMaria
Front of property

2. Cookie B

Cookie B
3.0 star property
Richmond
9.6 out of 10, Exceptional, (9 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
24 Sep - 25 Sep
Cookie B
Marina

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, (248 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 789 total
includes taxes & fees
27 Sep - 28 Sep
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
Lobby

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, (123 reviews)
"Great alternative to a house or hotel"
United States
Ashley Jo P.
The price is AED 422
AED 789 total
includes taxes & fees
27 Sep - 28 Sep
A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations
Coffee/tea maker, fridge, microwave, oven

5. The Studio@ Eanes Drug-Heart of the Historic District

The Studio@ Eanes Drug-Heart of the Historic District
Church Hill
10.0 out of 10, Exceptional, (97 reviews)
"Very clean, cozy and in an excellent location."
United States
Courtney W.
The price is AED 529
AED 688 total
includes taxes & fees
27 Sep - 28 Sep
The Studio@ Eanes Drug-Heart of the Historic District
Coffee/tea maker, fridge, microwave, oven

6. Qualla Park

Qualla Park
Chesterfield County
10.0 out of 10, Exceptional, (5 reviews)
"The home was beautiful and amazing! Host was amazing too! Highly recommend!"
United Kingdom
Shannon W.
The price is AED 661
AED 1,603 total
includes taxes & fees
24 Sep - 25 Sep
Qualla Park
Terrace/patio

7. 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, (5 reviews)
"Cute place. Very spacious and clean. Great communication. Would definitely stay again. Thank you!"
United States
Jeannie C.
The price is AED 364
AED 837 total
includes taxes & fees
29 Sep - 30 Sep
Newly finished basement suite in Midlothian. Very clean and spacious.
Coffee/tea maker, fridge, microwave, oven

8. Historic Haven in Church Hill in The Heart of the Historic District

Historic Haven in Church Hill in The Heart of the Historic District
Church Hill
10.0 out of 10, Exceptional, (80 reviews)
"Nice stay"
United States
Danelle B.
The price is AED 529
AED 688 total
includes taxes & fees
1 Oct - 2 Oct
Historic Haven in Church Hill in The Heart of the Historic District
Smart TV, fireplace

9. 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 most beautifully finished cottage! Host very responsive!! Loved it."
United States
Stephanie S.
The price is AED 366
AED 765 total
includes taxes & fees
5 Oct - 6 Oct
The Birdhouse - Cozy Cottage Retreat in Richmond
Property grounds

10. 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 347
AED 936 total
includes taxes & fees
29 Sep - 30 Sep
Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.
1 bedroom, WiFi (free)

11. 2 Queen Beds | Non-Smoking, Micfridge

2 Queen Beds | Non-Smoking, Micfridge
Petersburg VA
The price is AED 260
AED 286 total
includes taxes & fees
24 Sep - 25 Sep
2 Queen Beds | Non-Smoking, Micfridge
Terrace/patio

12. Private Garden Home w/ Large Fenced Yard + Gazebo

Private Garden Home w/ Large Fenced Yard + Gazebo
Broad Rock
10.0 out of 10, Exceptional, (4 reviews)
"Halfway point for our travels up north. Very clean, quiet, everything we needed!"
United States
Tammy K.
The price is AED 654
AED 1,431 total
includes taxes & fees
30 Sep - 1 Oct
Private Garden Home w/ Large Fenced Yard + Gazebo
Smart TV

13. Adorable 2-bedroom house with AC in charming Richmond VA

Adorable 2-bedroom house with AC in charming Richmond VA
Richmond
The price is AED 453
AED 664 total
includes taxes & fees
24 Sep - 25 Sep
Adorable 2-bedroom house with AC in charming Richmond VA
Coffee/tea maker, fridge, microwave, oven

14. Luxury Stay! 10 min away from Fort Lee.

Luxury Stay! 10 min away from Fort Lee.
Prince George
8.4 out of 10, Very good, (19 reviews)
"The home was very clean and very comfortable. Communication was excellent. We would definitely stay here again!"
United States
CHRIS
The price is AED 628
AED 1,633 total
includes taxes & fees
28 Sep - 29 Sep
Luxury Stay! 10 min away from Fort Lee.
Dining

15. 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, (92 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 347
AED 732 total
includes taxes & fees
28 Sep - 29 Sep
Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!
TV

16. Lovely 2 Bedroom in the Heart of The Fan

Lovely 2 Bedroom in the Heart of The Fan
Fan District
9.2 out of 10, Wonderful, (88 reviews)
"Great location and very walkable to restaurants, shopping and museums."
United States
Nancy D.
The price is AED 420
AED 1,304 total
includes taxes & fees
30 Sep - 1 Oct
Lovely 2 Bedroom in the Heart of The Fan
Exterior

17. Private bedroom and bath!

Private bedroom and bath!
Midlothian
6.0 out of 10, (2 reviews)
"We had a lacrosse tournament at River city sports plex. This was perfect location to stay for us. Friendly and amazing combination with host. Extremely pleased with our stay"
United States
Ridge W.
The price is AED 477
AED 858 total
includes taxes & fees
24 Sep - 25 Sep
Private bedroom and bath!
Living area

18. The Obsidian Retreat •Luxury Modern Stay • Recreation Area • Gated Home Sleeps 6

The Obsidian Retreat •Luxury Modern Stay • Recreation Area • Gated Home Sleeps 6
Woodhaven
The price is AED 674
AED 1,547 total
includes taxes & fees
27 Sep - 28 Sep
The Obsidian Retreat •Luxury Modern Stay • Recreation Area • Gated Home Sleeps 6
TV, books, offices

19. Oaks Retreat Carytown House Family Pet Friendly

Oaks Retreat Carytown House Family Pet Friendly
Randolph
9.0 out of 10, Wonderful, (20 reviews)
"Great quiet area, easy access to downtown and close to restaurants and parks. Nicely set up home with exceptional comforts for all"
United States
Thomas C.
The price is AED 455
AED 980 total
includes taxes & fees
29 Sep - 30 Sep
Oaks Retreat Carytown House Family Pet Friendly
TV

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

The Fan Comfort Stay near VCU Free Parking Fenced Yard
Fan District
9.4 out of 10, Exceptional, (30 reviews)
"Very convenient location, and great communication!"
United States
Katelyn F.
The price is AED 382
AED 708 total
includes taxes & fees
29 Sep - 30 Sep
The Fan Comfort Stay near VCU Free Parking Fenced Yard
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Hotel Reviews

Comfort Inn Chester - Richmond South

Comfort Inn Chester - Richmond South

8/10 Good
"Good"
Keyur 1-night trip
Posted 6 hours ago
Comfort Inn Chester - Richmond South

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?

Fantastic 5-bedroom Luxury home in charming Richmond: This vacation home rental outside of Chester has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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.