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

Southside Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Southside vacation rentals

A living room with a sofa, coffee table, TV, and a door with a 'No Smoking' sign.

1. 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.
$206 nightly
The price is $209
Oct 19 - Oct 20
Total with taxes and fees
The Birdhouse - Cozy Cottage Retreat in Richmond
IMG 6335

2. The Enchanted Studio

The Enchanted Studio
Huguenot
10.0 out of 10, Exceptional, (2 reviews)
"This was the most relaxing and peaceful visit.Nature all around and the most comfortable accommodations.So grateful to my generous host. Thank you!!"
United States
Mary B.
$171 nightly
The price is $194
Oct 5 - Oct 6
Total with taxes and fees
The Enchanted Studio
A modern living room with a grey sofa, a patterned rug, and a unique spherical light fixture.

3. 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.
$280 nightly
The price is $323
Oct 2 - Oct 3
Total with taxes and fees
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.

4. 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.
$406 nightly
The price is $464
Oct 5 - Oct 6
Total with taxes and fees
Charming 3-bedroom townhome with WiFi in delightful Richmond
A hotel room with two beds, a nightstand with a lamp, and artwork on the wall.

5. 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
$370 nightly
The price is $422
Oct 4 - Oct 5
Total with taxes and fees
The Obsidian Retreat •Luxury Modern Stay • Recreation Area • Gated Home Sleeps 6
A wooden gazebo with a bench and string lights, surrounded by trees.

6. 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.
$425 nightly
The price is $485
Oct 4 - Oct 5
Total with taxes and fees
Private Garden Home w/ Large Fenced Yard + Gazebo
A modern living room with a sectional sofa, a round coffee table, and a fluffy rug.

7. 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.
$733 nightly
The price is $838
Oct 4 - Oct 5
Total with taxes and fees
Renovated Modern Stylish “Vibrant” 4bdrm Home
A bunk bed with a headboard, a ceiling fan, and a window with curtains.

8. 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
$724 nightly
The price is $827
Oct 4 - Oct 5
Total with taxes and fees
The Lily Pad RVA- Charming Hidden Gem in the Southside of Richmond, Va.
A room with a fireplace, a mirror above it, and two leather chairs.

9. Nest & Rest | Private Studio | Free Parking

Nest & Rest | Private Studio | Free Parking
Fan District
9.8 out of 10, Exceptional, (46 reviews)
"Host was gracious and responsive, and the location was amazing! "
United States
Kelly M.
$132 nightly
The price is $147
Oct 20 - Oct 21
Total with taxes and fees
Nest & Rest | Private Studio | Free Parking
A bedroom with a bed, a TV, and built-in shelving with decorative items.

10. 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.
$105 nightly
The price is $120
Oct 12 - Oct 13
Total with taxes and fees
Magnolias, a chill out place.
A high-ceilinged interior with skylights and built-in shelving.

11. Heart of the Arts - New King Suite on West Broad Condo’s next to Quirk MCV VCU

Heart of the Arts - New King Suite on West Broad Condo’s next to Quirk MCV VCU
Downtown Richmond
9.8 out of 10, Exceptional, (56 reviews)
"Great stay."
United States
Brian D.
$181 nightly
The price is $207
Oct 5 - Oct 6
Total with taxes and fees
Heart of the Arts - New King Suite on West Broad Condo’s next to Quirk MCV VCU
A spacious restaurant with high ceilings, large windows, and a central bar area.

12. 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
$190 nightly
The price is $217
Oct 4 - Oct 5
Total with taxes and fees
Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!
A modern kitchen with stainless steel appliances, a white countertop, and pendant lighting.

13. Downtown Living in Richmond's Amazing Shockoe Bottom

Downtown Living in Richmond's Amazing Shockoe Bottom
Downtown Richmond
8.6 out of 10, Excellent, (35 reviews)
"Was I great place to stay! Very responsive and gave all the info you need to make the trip and stay easy! "
United States
Dillon D.
$306 nightly
The price is $327
Oct 5 - Oct 6
Total with taxes and fees
Downtown Living in Richmond's Amazing Shockoe Bottom
A gray sectional sofa with patterned cushions, a white door, decorative wall art, a window with blinds, and a small table with a lamp.

14. 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.
$180 nightly
The price is $200
Oct 4 - Oct 5
Total with taxes and fees
The Fan Comfort Stay near VCU Free Parking Fenced Yard
A corner building with large windows and a black awning.

15. RVA Arts District near VCU MCV

RVA Arts District near VCU MCV
Downtown Richmond
9.6 out of 10, Exceptional, (28 reviews)
"Great spot above the coolest music store in downtown Richmond. Easy stay and very enjoyable!"
United States
Benjamin
$181 nightly
The price is $207
Oct 5 - Oct 6
Total with taxes and fees
RVA Arts District near VCU MCV
A compact kitchen with a refrigerator, stove, microwave, and a trash bin.

16. Cozy studio apartment in tranquil Richmond with AC and gym access

Cozy studio apartment in tranquil Richmond with AC and gym access
Downtown Richmond
6.0 out of 10, (2 reviews)
"Good for a simple overnight"
United States
Stephanie K.
$116 nightly
The price is $133
Oct 4 - Oct 5
Total with taxes and fees
Cozy studio apartment in tranquil Richmond with AC and gym access
A bedroom with a bed, a wooden nightstand, a desk, and a shelving unit.

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
9.8 out of 10, Exceptional, (13 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.
$225 nightly
The price is $257
Oct 27 - Oct 28
Total with taxes and fees
Private Guest house with Parking and Wi-Fi in a Central Location
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.
$196 nightly
The price is $226
Oct 26 - Oct 27
Total with taxes and fees
Newly finished basement suite in Midlothian. Very clean and spacious.
A modern living room with a teal sofa, a coffee table, and a TV on a stand. There is a 'WELCOME' sign on the wall and a framed picture above the sofa.

19. 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.
$334 nightly
The price is $357
Oct 5 - Oct 6
Total with taxes and fees
Lovely 2 Bedroom in the Heart of The Fan
A patio with a wooden deck, a gray outdoor sofa with a yellow pillow, a wooden chair, a small round table, and a spiral staircase leading to a balcony.

20. 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.
$195 nightly
The price is $223
Oct 12 - Oct 13
Total with taxes and fees
Colorful private guesthouse in charming Richmond with Parking
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

Holiday Inn & Suites Richmond West End

Holiday Inn & Suites Richmond West End

10/10 Excellent
"Very convenient to everywhere I needed to go. The staff was very kind and helpful. Check in and out was very quick and efficient."
Steva 4-night trip
Posted 2 hours ago
Holiday Inn & Suites Richmond West End

Find out more about Southside

Everything you need to know about Southside vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Southside vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Southside vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Southside vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Southside. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Southside in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $213 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Southside rentals

At Expedia, we put the best Southside vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Southside rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Southside vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Southside. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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