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Chester Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

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 ￥18,732
￥54,007 total
includes taxes & fees
Sep 7 - Sep 8
Game Room + Yard: Updated House in Chester!
A calm lake with a dock and a small building, surrounded by trees.

2. 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 ￥33,313
￥43,314 total
includes taxes & fees
Sep 6 - Sep 7
MV GiaMaria
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, (243 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 ￥17,952
￥33,000 total
includes taxes & fees
Sep 14 - Sep 15
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
A dock area with boats, a covered seating area, and a sign indicating no trespassing for boat owners and guests only.

4. 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 ￥34,147
￥46,732 total
includes taxes & fees
Sep 6 - Sep 7
Cookie B
A bedroom with a large bed, two bedside tables, a chair, and a window with curtains.

5. Family friendly! Recline at Timberline..

Family friendly! Recline at Timberline..
South chesterfield
9.4 out of 10, Exceptional, (56 reviews)
"This is a beautiful home nice area We all enjoyed it I'm thinking to come back soon"
United States
golden c.
The price is ￥17,171
￥51,387 total
includes taxes & fees
Sep 23 - Sep 24
Family friendly! Recline at Timberline..
A grand lobby with a large Christmas tree, marble columns, and a red carpeted floor.

6. 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, (121 reviews)
"Great alternative to a house or hotel"
United States
Ashley Jo P.
The price is ￥17,952
￥33,535 total
includes taxes & fees
Sep 7 - Sep 8
A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations
A bedroom with a bed, a ceiling fan, a window with curtains, and a wall with framed artwork.

7. The Lily Pad RVA- Charming Hidden Gem in the Southside of Richmond, Va.

The Lily Pad RVA- Charming Hidden Gem in the Southside of Richmond, Va.
Davee Gardens
The price is ￥62,440
￥129,157 total
includes taxes & fees
Sep 10 - Sep 11
The Lily Pad RVA- Charming Hidden Gem in the Southside of Richmond, Va.
A modern kitchen with a central island, stainless steel appliances, and bar stools.

8. 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, (95 reviews)
"Very clean, cozy and in an excellent location."
United States
Courtney W.
The price is ￥22,635
￥29,435 total
includes taxes & fees
Sep 6 - Sep 7
The Studio@ Eanes Drug-Heart of the Historic District
A modern kitchen with white cabinetry, a stainless steel refrigerator, a built-in oven, and a microwave.

9. 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, (79 reviews)
"Nice stay"
United States
Danelle B.
The price is ￥23,415
￥30,505 total
includes taxes & fees
Sep 7 - Sep 8
Historic Haven in Church Hill in The Heart of the Historic District
A modern kitchen with a built-in refrigerator, a grey wall with an air conditioning unit, and a staircase leading to a landing.

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

Adorable 2-bedroom house with AC in charming Richmond VA
Richmond
The price is ￥19,669
￥34,965 total
includes taxes & fees
Sep 10 - Sep 11
Adorable 2-bedroom house with AC in charming Richmond VA
A rural landscape with a dirt path, grassy areas, and a building with a green roof.

11. 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)
"The location is beautiful! Kristina was very prompt in answering my questions and very accommodating. Wonderful stay."
United States
Connie D.
The price is ￥14,751
￥39,440 total
includes taxes & fees
Sep 7 - Sep 8
Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.
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.

12. 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 ￥7,641
￥10,069 total
includes taxes & fees
Sep 5 - Sep 6
2 Full Beds|Non-Smoking
A kitchen with a wooden island, stainless steel appliances, and a chandelier.

13. 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 ￥28,098
￥68,122 total
includes taxes & fees
Sep 10 - Sep 11
Qualla Park
A living room with a sofa, coffee table, TV, and a door with a 'No Smoking' sign.

14. 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 ￥15,571
￥32,697 total
includes taxes & fees
Sep 17 - Sep 18
The Birdhouse - Cozy Cottage Retreat in Richmond
A wooden gazebo with a bench and string lights, surrounded by trees.

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

Private Garden Home w/ Large Fenced Yard + Gazebo
Broad Rock
10.0 out of 10, Exceptional, (2 reviews)
"We had a great stay here for two nights! The beds were extremely comfortable and it was quiet and peaceful sleeping there both nights. We enjoyed the backyard very much - both our pets and kids. My son thought the gazebo with twinkle lights out back was so magical. :) We appreciate the cleanliness of the place and would only have appreciated a little space with maybe kids’ books, puzzles, or blocks or something. My young kiddos go crazy for those things when we stay at vacation rentals and it...
United States
Stacie C.
The price is ￥26,357
￥59,337 total
includes taxes & fees
Sep 14 - Sep 15
Private Garden Home w/ Large Fenced Yard + Gazebo
A bedroom with a bed, a TV, and built-in shelving with decorative items.

16. Magnolias, a chill out place.

Magnolias, a chill out place.
Richmond
9.2 out of 10, Wonderful, (24 reviews)
"Would stay again!"
United States
Amir D.
The price is ￥10,115
￥18,693 total
includes taxes & fees
Sep 9 - Sep 10
Magnolias, a chill out place.
A modern kitchen with white cabinets, a stainless steel oven, a microwave, and a marble dining table.

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

Luxury Stay! 10 min away from Fort Lee.
Prince George
8.6 out of 10, Excellent, (18 reviews)
"The home was very clean and very comfortable. Communication was excellent. We would definitely stay here again!"
United States
CHRIS
The price is ￥23,462
￥65,264 total
includes taxes & fees
Sep 8 - Sep 9
Luxury Stay! 10 min away from Fort Lee.
A wooden deck with a table and chairs, surrounded by potted plants and a wooden fence.

18. 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 ￥14,131
￥33,809 total
includes taxes & fees
Sep 20 - Sep 21
Newly finished basement suite in Midlothian. Very clean and spacious.
A living room with a beige sofa, a round black coffee table, a large window, and a painting of a tree.

19. Charming 3-bedroom townhome with WiFi in delightful Richmond

Charming 3-bedroom townhome with WiFi in delightful Richmond
Jahnke
10.0 out of 10, Exceptional, (7 reviews)
"Check-in was simple, good communication, property very much as described/depicted in the listing. Perfect location for our needs. "
United States
Mary C.
The price is ￥31,438
￥73,488 total
includes taxes & fees
Sep 8 - Sep 9
Charming 3-bedroom townhome with WiFi in delightful Richmond
A living room with a fireplace, a television mounted above it, and a ceiling fan. There are two chairs and a sofa.

20. Walk to VCU & Allianz Amphitheater Cozy & Clean

Walk to VCU & Allianz Amphitheater Cozy & Clean
Oregon Hill
The price is ￥18,888
￥52,268 total
includes taxes & fees
Sep 8 - Sep 9
Walk to VCU & Allianz Amphitheater Cozy & Clean
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

Country Inn & Suites by Radisson, Richmond West at I-64, VA

Country Inn & Suites by Radisson, Richmond West at I-64, VA

10/10 Excellent
"The staff was very responsive when we realized we needed a more accessible toilet, and got us a new room immediately! The only issue we had was that the indoor pool was undergoing maintenance for the three nights of our stay so we were not able to use it. That is the reason for the 4-star rating on maintenance. Otherwise, our stay at the Country Inn & Suites by Radisson was enjoyable and an excellent value. Would stay here again."
Nikki Susong 3-night trip
Posted 11 hours ago
Country Inn & Suites by Radisson, Richmond West at I-64, VA

Find out more about Chester

Search for holiday rentals in Chester on Expedia! You can easily find your home rentals, villas, holiday apartments in Chester using one of the methods below:

  • View our selection of featured holiday rentals in Chester
  • Use the map to find apartments and other holiday homes in the Chester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chester while they last

Look no further and take a look at our great range of rental properties in 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?

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. Point of Rocks Park and Appomattox River 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.