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Chester Vacation Rentals

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Chester vacation rentals

House (3 Bedrooms) | Interior

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
9 Aug - 10 Aug
Game Room + Yard: Updated House in Chester!
Lobby

2. 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, (120 reviews)
"Quaint, quiet, and cozy. Clean. Just what was wanted for a few quiet days. "
United States
norma W.
The price is AED 422
AED 789 total
includes taxes & fees
12 Aug - 13 Aug
A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations
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, (242 reviews)
"Peaceful, welcoming and inviting all describe our stay. I would highly recommend this houseboat for your visit to Richmond."
United States
FARYL H.
The price is AED 422
AED 781 total
includes taxes & fees
9 Aug - 10 Aug
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
3 bedrooms, desk, iron/ironing board, WiFi (free)

4. Family friendly! Recline at Timberline..

Family friendly! Recline at Timberline..
South chesterfield
9.2 out of 10, Wonderful, (53 reviews)
"all in all a comfortable stay."
United States
James W.
Family friendly! Recline at Timberline..
Front of property

5. Cookie B

Cookie B
3.0 star property
Richmond
9.6 out of 10, Exceptional, (8 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
12 Aug - 13 Aug
Cookie B
View from property

6. 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
23 Aug - 24 Aug
MV GiaMaria
Property grounds

7. 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, (6 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 915 total
includes taxes & fees
10 Aug - 11 Aug
Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.
Smart TV, fireplace

8. The Birdhouse - Cozy Cottage Retreat in Richmond

The Birdhouse - Cozy Cottage Retreat in Richmond
Swansboro West
10.0 out of 10, Exceptional, (4 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 765 total
includes taxes & fees
12 Aug - 13 Aug
The Birdhouse - Cozy Cottage Retreat in Richmond
Dining

9. Carytown cozy nest private room Fenced Yard

Carytown cozy nest private room Fenced Yard
Carytown
9.8 out of 10, Exceptional, (29 reviews)
"Everything was great for our stay! We didn't stay there long but was the perfect location near Carytown. We extended our stay, and the hosts were beyond accommodating. "
United States
Bonnie W.
The price is AED 253
AED 506 total
includes taxes & fees
12 Aug - 13 Aug
Carytown cozy nest private room Fenced Yard
Coffee/tea maker, fridge, microwave, oven

10. 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, (91 reviews)
"Great option and neighborhood- enjoyed the stay"
United States
Gary P.
The price is AED 514
AED 672 total
includes taxes & fees
11 Aug - 12 Aug
The Studio@ Eanes Drug-Heart of the Historic District
Coffee/tea maker, fridge, microwave, oven

11. 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, (75 reviews)
"Nice stay"
United States
Danelle B.
The price is AED 551
AED 714 total
includes taxes & fees
11 Aug - 12 Aug
Historic Haven in Church Hill in The Heart of the Historic District
Terrace/patio

12. 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 820 total
includes taxes & fees
7 Sep - 8 Sep
Newly finished basement suite in Midlothian. Very clean and spacious.
TV

13. 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, (87 reviews)
"Clean area, very easy to get in and out of, and great "
United States
Ryanne T.
The price is AED 420
AED 1,304 total
includes taxes & fees
10 Aug - 11 Aug
Lovely 2 Bedroom in the Heart of The Fan
Outdoor dining

14. Colorful private guesthouse in charming Richmond with Parking

Colorful private guesthouse in charming Richmond with Parking
Northern Barton Heights
10.0 out of 10, Exceptional, (6 reviews)
"I like this location. It is close to where I was hanging out in Richmond. The check-in was super easy, and the decorations are fun!"
United States
Jim H.
The price is AED 386
AED 806 total
includes taxes & fees
10 Aug - 11 Aug
Colorful private guesthouse in charming Richmond with Parking
Fridge, microwave, oven, stovetop

15. Luxe King Bd W Resort Amenities

Luxe King Bd W Resort Amenities
Moseley
9.2 out of 10, Wonderful, (9 reviews)
"Hotel options in this area are awful; this condo is a great alternative. Everything is basic but completely serviceable and completely met our needs. The location close to Brandermill nursing/assisted living is perfect."
United States
Lisa H.
The price is AED 304
AED 745 total
includes taxes & fees
13 Aug - 14 Aug
Luxe King Bd W Resort Amenities
1 bedroom, in-room safe, WiFi (free), bed sheets

16. Magnolias, a chill out place.

Magnolias, a chill out place.
Richmond
9.2 out of 10, Wonderful, (23 reviews)
"Would stay again!"
United States
Amir D.
The price is AED 264
AED 470 total
includes taxes & fees
8 Sep - 9 Sep
Magnolias, a chill out place.
1 bedroom, desk, iron/ironing board, WiFi

17. Private Guest house with Parking and Wi-Fi in a Central Location

Private Guest house with Parking and Wi-Fi in a Central Location
Virginia Union
9.6 out of 10, Exceptional, (10 reviews)
"Amazing space. Great response time, our host was super friendly & helpful. The house was everything we were looking for and more, it was beautiful and the location was very convenient! "
United States
Michelle S.
The price is AED 299
AED 917 total
includes taxes & fees
8 Sep - 9 Sep
Private Guest house with Parking and Wi-Fi in a Central Location
Dining

18. Cozy 2-bedroom apartment in beautiful Fan District

Cozy 2-bedroom apartment in beautiful Fan District
Fan District
10.0 out of 10, Exceptional, (1 review)
"Check in was quick and easy. Our host communicated everything we needed to make the stay seamless. The apartment was very clean and had everything we needed to be comfortable. Location was perfect. Walkable to Careytown with fun shopping and plenty of places to eat. We so enjoyed the stay!"
United States
Dorothy A S.
The price is AED 364
AED 1,024 total
includes taxes & fees
1 Sep - 2 Sep
Cozy 2-bedroom apartment in beautiful Fan District
Exterior

19. 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 867 total
includes taxes & fees
6 Sep - 7 Sep
Private bedroom and bath!
TV, books, offices

20. Oaks Retreat Carytown House: Family & Pet Friendly

Oaks Retreat Carytown House: Family & Pet Friendly
Randolph
9.2 out of 10, Wonderful, (17 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 459
AED 1,018 total
includes taxes & fees
10 Aug - 11 Aug
Oaks Retreat Carytown House: Family & Pet Friendly
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

Omni Richmond Hotel

Omni Richmond Hotel

10/10 Excellent
"This hotel has a wonderful shuttle bus driver who took me to a few places, like Walmart and Carytown. I really liked Adrian who was very helpful in getting me a taxi when I needed one. All the staff at this hotel were very pleasant and will to go the extra mile. Thanks Donna Toronto"
Donna 2-night trip
Posted 8 hours ago
Omni Richmond Hotel

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?

Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!: This vacation home rental outside of Chester has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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.