Chester Vacation Rentals

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Check prices for these dates

Our top choices for Chester vacation homes

1. 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 CA $155
CA $325 total
includes taxes & fees
Nov 15 - Nov 16
Newly finished basement suite in Midlothian. Very clean and spacious.

2. Luxe Cottage - South Chesterfield Stylishly renovated, w/ large master suite

Luxe Cottage - South Chesterfield Stylishly renovated, w/ large master suite
Ettrick
10.0 out of 10, Exceptional, (22 reviews)
"The property was exactly as described. Everything we needed was on site. The owner communicated check-in details the day before our arrival date so there was no guesswork. This was our first VRBO experience and it was great. We visit the area twice a year, and we will be staying here again next spring."
United States
john
The price is CA $307
CA $707 total
includes taxes & fees
Nov 10 - Nov 11
Luxe Cottage - South Chesterfield Stylishly renovated, w/ large master suite

3. Qualla Park

Qualla Park
Chesterfield County
10.0 out of 10, Exceptional, (7 reviews)
"The home was beautiful and amazing! Host was amazing too! Highly recommend!"
United Kingdom
Shannon W.
The price is CA $284
CA $601 total
includes taxes & fees
Nov 19 - Nov 20
Qualla Park

4. 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 CA $182
CA $313 total
includes taxes & fees
Nov 27 - Nov 28
Private bedroom and bath!

5. Close to Fort Gregg-Adams, VSU & Southside Medical – Comfort & Convenience

Close to Fort Gregg-Adams, VSU & Southside Medical – Comfort & Convenience
Petersburg
8.8 out of 10, Excellent, (5 reviews)
"Big yard."
United States
Michael O.
The price is CA $202
CA $579 total
includes taxes & fees
Nov 21 - Nov 22
Close to Fort Gregg-Adams, VSU & Southside Medical – Comfort & Convenience

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

Luxury Stay! 10 min away from Fort Lee.
Prince George
8.6 out of 10, Excellent, (21 reviews)
"perfect stay for the wedding we went to at the barns of kanak!! super close and good safe neighborhood "
United States
Rachael O.
The price is CA $228
CA $579 total
includes taxes & fees
Nov 10 - Nov 11
Luxury Stay! 10 min away from Fort Lee.

7. Charming 1-bedroom suite with WiFi and AC in Bon Air

Charming 1-bedroom suite with WiFi and AC in Bon Air
Bon Air
8.8 out of 10, Excellent, (11 reviews)
"It was a nice stay the host was prompt and answered any questions or concerns right away, she was very polite and helpful to me and family "
United States
Jessica H.
The price is CA $146
CA $380 total
includes taxes & fees
Nov 18 - Nov 19
Charming 1-bedroom suite with WiFi and AC in Bon Air

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

Private Garden Home w/ Large Fenced Yard + Gazebo
Broad Rock
10.0 out of 10, Exceptional, (6 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 CA $216
CA $479 total
includes taxes & fees
Nov 8 - Nov 9
Private Garden Home w/ Large Fenced Yard + Gazebo

9. 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
8.0 out of 10, Very good, (1 review)
"It was clean and nicely Renovated. It was clear, that they have put in work to improve the house. The showers could use a user manual."
United States
Lisa J.
The price is CA $221
CA $518 total
includes taxes & fees
Nov 18 - Nov 19
The Obsidian Retreat •Luxury Modern Stay • Recreation Area • Gated Home Sleeps 6

10. Carytown Family Home Free Parking Fenced Yard

Carytown Family Home Free Parking Fenced Yard
Byrd Park
9.0 out of 10, Wonderful, (22 reviews)
"Clean rooms and a very communicative host!"
United States
Kyla G.
The price is CA $174
CA $372 total
includes taxes & fees
Nov 10 - Nov 11
Carytown Family Home Free Parking Fenced Yard

11. River City Modern Retreat

River City Modern Retreat
Manchester
The price is CA $177
CA $351 total
includes taxes & fees
Nov 9 - Nov 10
River City Modern Retreat

12. 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, (8 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 CA $280
CA $625 total
includes taxes & fees
Nov 9 - Nov 10
Charming 3-bedroom townhome with WiFi in delightful Richmond

13. 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 CA $177
CA $377 total
includes taxes & fees
Nov 9 - Nov 10
Oaks Retreat Carytown House Family Pet Friendly

14. 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 CA $103
CA $234 total
includes taxes & fees
Nov 9 - Nov 10
Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!

15. Sweet Vine Of MIne

Sweet Vine Of MIne
Fan District
The price is CA $191
CA $357 total
includes taxes & fees
Nov 9 - Nov 10
Sweet Vine Of MIne

16. Walk to Allianz Urban Oasis in Oregon Hill

Walk to Allianz Urban Oasis in Oregon Hill
Oregon Hill
10.0 out of 10, Exceptional, (1 review)
"We really enjoyed our stay, Friday - Sunday. The apartment is exactly as shown in the photos, clean, comfortable and spacious. Street park was easily available and the location is good. Note: as stated in the description, the area is very close to VCU, lots of students living in the area. They were very loud on Friday and Saturday late night into the early morning... bring earplugs, it helps a lot."
United States
margaret
The price is CA $187
CA $467 total
includes taxes & fees
Nov 10 - Nov 11
Walk to Allianz Urban Oasis in Oregon Hill

17. Serene 6-bedroom house with AC in charming Midlothian

Serene 6-bedroom house with AC in charming Midlothian
Brandermill
The price is CA $574
CA $1,192 total
includes taxes & fees
Nov 10 - Nov 11
Serene 6-bedroom house with AC in charming Midlothian

18. 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 CA $565
CA $1,108 total
includes taxes & fees
Nov 15 - Nov 16
The Lily Pad RVA- Charming Hidden Gem in the Southside of Richmond, Va.

19. Cozy and spacious 3BR in the heart of VCU & Downtown

Cozy and spacious 3BR in the heart of VCU & Downtown
Carver
10.0 out of 10, Exceptional, (12 reviews)
"The house was very welcoming, clean, had spacious!"
United States
Josh L.
The price is CA $210
CA $550 total
includes taxes & fees
Nov 8 - Nov 9
Cozy and spacious 3BR in the heart of VCU & Downtown

20. Earth & Ember -Cottage House Retreat!

Earth & Ember -Cottage House Retreat!
North Highland Park
The price is CA $175
CA $373 total
includes taxes & fees
Nov 27 - Nov 28
Earth & Ember -Cottage House Retreat!
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.

Learn more about Chester

Stroll through the historic downtown where local shops and the 1939 train station offer a glimpse into small-town Virginia charm. Nearby Henricus Historical Park and Dutch Gap Conservation Area provide perfect spots for history buffs to explore 17th-century settlements and nature lovers to hike riverside trails.

An aerial view of a residential area with houses, roads, and a water tower.

Top reviews in Chester

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