An aerial view of a large parking lot surrounded by green fields and a highway.

Holiday Homes in Southside

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Southside holiday homes

A modern living room with a grey sofa, a patterned rug, and a unique spherical light fixture.

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

Charming 1-bedroom suite with WiFi and AC in Bon Air
Bon Air
9.0 out of 10, Wonderful, (10 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 €282
includes taxes & fees
21 Sept - 22 Sept
Charming 1-bedroom suite with WiFi and AC in Bon Air
A living room with a beige sofa, a round black coffee table, a large window, and a painting of a tree.

2. 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 €375
includes taxes & fees
1 Sept - 2 Sept
Charming 3-bedroom townhome with WiFi in delightful Richmond
A wooden gazebo with a bench and string lights, surrounded by trees.

3. 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 €310
includes taxes & fees
14 Sept - 15 Sept
Private Garden Home w/ Large Fenced Yard + Gazebo
A modern living room with a sectional sofa, a round coffee table, and a fluffy rug.

4. Renovated Modern Stylish “Vibrant” 4bdrm Home

Renovated Modern Stylish “Vibrant” 4bdrm Home
Beaufont
9.4 out of 10, Exceptional, (10 reviews)
"Loved it"
United States
Brittianey T.
The price is €729
includes taxes & fees
1 Sept - 2 Sept
Renovated Modern Stylish “Vibrant” 4bdrm Home

5. 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 Lily Pad RVA- Charming Hidden Gem in the Southside of Richmond, Va.
A living room with two beige armchairs, a small table, and a black door.

6. Cozy Bungalow | 3 Parking Spots | Fully Fenced Yard

Cozy Bungalow | 3 Parking Spots | Fully Fenced Yard
Richmond
10.0 out of 10, Exceptional, (9 reviews)
"The place was very nice and as advertised. Big backyard for your dog."
United States
Joseph
Cozy Bungalow | 3 Parking Spots | Fully Fenced Yard
A modern living room with a dark wood floor, a grey sofa, a black coffee table, and a dining area with a green table and chairs.

7. Carytown Home/Free Parking/Fenced Yard/Family-Friendly/4TVs

Carytown Home/Free Parking/Fenced Yard/Family-Friendly/4TVs
Byrd Park
9.0 out of 10, Wonderful, (20 reviews)
"Great stay! Friendly host and nice location. "
United States
Monte H.
The price is €238
includes taxes & fees
31 Aug - 1 Sept
Carytown Home/Free Parking/Fenced Yard/Family-Friendly/4TVs

8. Oaks Retreat Carytown House: Family & Pet Friendly

Oaks Retreat Carytown House: Family & Pet Friendly
Randolph
9.0 out of 10, Wonderful, (19 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 €238
includes taxes & fees
31 Aug - 1 Sept
Oaks Retreat Carytown House: Family & Pet Friendly
A living room with a gray sofa, a brown leather armchair, a coffee table, a side table with a lamp, and a ceiling fan.

9. The Sweet Retreat RVA • Fenced Yard • Fire Pit • Parking

The Sweet Retreat RVA • Fenced Yard • Fire Pit • Parking
Sauer's Gardens
9.6 out of 10, Exceptional, (75 reviews)
"This house was perfect for a weekend away. The house had all of the little things that you may need. Mei was great to deal with as well!"
United States
Jessica P.
The price is €252
includes taxes & fees
31 Aug - 1 Sept
The Sweet Retreat RVA • Fenced Yard • Fire Pit • Parking
A living room with a large potted bamboo plant, a flat-screen TV, a wooden TV stand with decorative items, and a portable air purifier.

10. Charming Ranch Home/pet friendly/fenced yard/4TVs

Charming Ranch Home/pet friendly/fenced yard/4TVs
Sherwood Park
9.6 out of 10, Exceptional, (4 reviews)
"Comfortable and pet friendly. "
United States
Jennifer P.
The price is €270
includes taxes & fees
29 Sept - 30 Sept
Charming Ranch Home/pet friendly/fenced yard/4TVs
A wooden deck with a table and chairs, surrounded by potted plants and a wooden fence.

11. 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 €190
includes taxes & fees
20 Sept - 21 Sept
Newly finished basement suite in Midlothian. Very clean and spacious.
A living room with a sofa, ottoman, and coffee table, a dining area with a table and chairs, and a ceiling fan.

12. Cozy Retreat w/ Fenced Yard & Fire Pit

Cozy Retreat w/ Fenced Yard & Fire Pit
Monument Avenue Park
9.2 out of 10, Wonderful, (35 reviews)
"The house was perfect for our stay and very pet friendly as described. Great location in Richmond. We would stay there again!"
United States
Ashley O.
The price is €248
includes taxes & fees
2 Sept - 3 Sept
Cozy Retreat w/ Fenced Yard & Fire Pit
A living room with a fireplace, a television mounted above it, and a ceiling fan. There are two chairs and a sofa.

13. Walk to VCU & Allianz Amphitheater Cozy & Clean

Walk to VCU & Allianz Amphitheater Cozy & Clean
Oregon Hill
The price is €292
includes taxes & fees
31 Aug - 1 Sept
Walk to VCU & Allianz Amphitheater Cozy & Clean
A living room with a dark-colored sofa, a wooden floor, a ceiling fan, and a staircase leading to an upper level.

14. 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, (9 reviews)
"The house was very welcoming, clean, had spacious!"
United States
Josh L.
The price is €345
includes taxes & fees
28 Sept - 29 Sept
Cozy and spacious 3BR in the heart of VCU & Downtown

15. Earth & Ember -Cottage House Retreat!

Earth & Ember -Cottage House Retreat!
North Highland Park
The price is €255
includes taxes & fees
31 Aug - 1 Sept
Earth & Ember -Cottage House Retreat!
A black door with the number 1920 above it, flanked by two wicker chairs with cushions, a potted plant, and a doormat.

16. Charming Fan District Getaway

Charming Fan District Getaway
Fan District
9.8 out of 10, Exceptional, (34 reviews)
"Comfortable house for 3 friends to get together. Kitchen had everything we needed. Easy street parking. Easy walk to bus station to get to the State Capitol area and restaurants. Quick drive to the Botanical Garden, Virginia Fine Arts Museum and historical houses. Safe and walkable area."
United States
Victoria L B.
The price is €450
includes taxes & fees
7 Sept - 8 Sept
Charming Fan District Getaway

17. Cozy walkable downtown retreat, 3 minutes to VCU

Cozy walkable downtown retreat, 3 minutes to VCU
Downtown Richmond
8.4 out of 10, Very good, (32 reviews)
"Super cute and charming home for a quick stay. The home is spacious, located close to downtown, and was clean."
United States
Sarah B.
The price is €425
includes taxes & fees
2 Sept - 3 Sept
Cozy walkable downtown retreat, 3 minutes to VCU

18. Spacious 3 BR Home with Fire Pit & Fenced Backyard - Pet Friendly

Spacious 3 BR Home with Fire Pit & Fenced Backyard - Pet Friendly
North Highland Park
Spacious 3 BR Home with Fire Pit & Fenced Backyard - Pet Friendly
A living room with a fireplace, a sofa, a chair, and a coffee table.

19. Peaceful 2 BR Unit with Large Fenced Backyard-Family & Pet Friendly

Peaceful 2 BR Unit with Large Fenced Backyard-Family & Pet Friendly
Glen Allen
9.0 out of 10, Wonderful, (24 reviews)
"Easy place to get in and out of, comfortable, would definitely stay again."
United States
Steve S.
Peaceful 2 BR Unit with Large Fenced Backyard-Family & Pet Friendly
A spacious living room with a dark leather sofa, a blue armchair, and a red patterned rug.

20. Charming Historic Home-Walk to Carytown-Fence-Pet Friendly-Hotel-grade Towels

Charming Historic Home-Walk to Carytown-Fence-Pet Friendly-Hotel-grade Towels
Carytown
10.0 out of 10, Exceptional, (10 reviews)
"Great location "
United States
Darrin B.
Charming Historic Home-Walk to Carytown-Fence-Pet Friendly-Hotel-grade Towels
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 Southside Hotel Reviews

Drury Plaza Hotel Richmond

Drury Plaza Hotel Richmond

10/10 Excellent
"Always try to stay at Drury hotels when possible. Never had a bad experience, always clean, comfortable and welcoming."
Lynn 1-night trip
Posted 8 hours ago
Drury Plaza Hotel Richmond

Find out more about Southside

Southside Holiday Homes information

Number of reviews
273
Accommodation
332 Holiday Homes
Lowest Price
€190
Highest Price
€729

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