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

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
Aug 27 - Aug 28
Total with taxes and fees
The Birdhouse - Cozy Cottage Retreat in Richmond
A modern living room with a grey sofa, a patterned rug, and a unique spherical light fixture.

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

Charming 1-bedroom suite with WiFi and AC in Bon Air
Bon Air
9.8 out of 10, Exceptional, (9 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.
$284 nightly
The price is $327
Aug 25 - Aug 26
Total with taxes and fees
Charming 1-bedroom suite with WiFi and AC in Bon Air
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.
$281 nightly
The price is $321
Aug 25 - Aug 26
Total with taxes and fees
Private Garden Home w/ Large Fenced Yard + Gazebo
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, (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.
$355 nightly
The price is $406
Sep 1 - Sep 2
Total with taxes and fees
Charming 3-bedroom townhome with WiFi in delightful Richmond
A cozy lounge area with a fireplace, comfortable seating, and large windows offering views of the street.

5. Cozy 1BR Apt Private Balcony, Gym, Yoga, Pool & Co-Working Space

Cozy 1BR Apt Private Balcony, Gym, Yoga, Pool & Co-Working Space
Old Town Manchester
$303 nightly
The price is $346
Aug 28 - Aug 29
Total with taxes and fees
Cozy 1BR Apt Private Balcony, Gym, Yoga, Pool & Co-Working Space

6. 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.
$200 nightly
The price is $227
Aug 26 - Aug 27
Total with taxes and fees
The Enchanted Studio
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)
"The overall experience was nice. Everything was there as advertised, and we would definitely stay there again"
United States
Johnny W.
$743 nightly
The price is $849
Aug 25 - Aug 26
Total with taxes and fees
Renovated Modern Stylish “Vibrant” 4bdrm Home

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
Aug 25 - Aug 26
Total with taxes and fees
The Lily Pad RVA- Charming Hidden Gem in the Southside of Richmond, Va.

9. Carytown cozy nest private room Fenced Yard

Carytown cozy nest private room Fenced Yard
Carytown
9.8 out of 10, Exceptional, (32 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.
$124 nightly
The price is $138
Aug 27 - Aug 28
Total with taxes and fees
Carytown cozy nest private room Fenced Yard
A round table with a dark surface, surrounded by four beige chairs with metal legs. There is a potted plant on the table.

10. 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.
$223 nightly
The price is $255
Aug 25 - Aug 26
Total with taxes and fees
Cozy 2-bedroom apartment in beautiful Fan District
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.

11. 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)
"Great location and very walkable to restaurants, shopping and museums."
United States
Nancy D.
$336 nightly
The price is $360
Sep 21 - Sep 22
Total with taxes and fees
Lovely 2 Bedroom in the Heart of The Fan
A room with a fireplace, a mirror above it, and two leather chairs.

12. 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
Sep 21 - Sep 22
Total with taxes and fees
Nest & Rest | Private Studio | Free Parking
A living room with a grey sofa, patterned throw, and a patterned rug.

13. Apartment 2B Premium 1-bedroom and 1- Living Room in FAN Area Richmond

Apartment 2B Premium 1-bedroom and 1- Living Room in FAN Area Richmond
Fan District
10.0 out of 10, Exceptional, (27 reviews)
"Great place in a convenient location!"
United States
Allen D.
$214 nightly
The price is $244
Sep 1 - Sep 2
Total with taxes and fees
Apartment 2B Premium 1-bedroom and 1- Living Room in FAN Area Richmond
A bedroom with a bed, a wooden nightstand, a desk, and a shelving unit.

14. 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.
$207 nightly
The price is $236
Sep 9 - Sep 10
Total with taxes and fees
Private Guest house with Parking and Wi-Fi in a Central Location
A modern kitchen with a central island, stainless steel appliances, and bar stools.

15. 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, (93 reviews)
"Very clean, cozy and in an excellent location."
United States
Courtney W.
$160 nightly
The price is $183
Aug 26 - Aug 27
Total with taxes and fees
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.

16. 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, (77 reviews)
"Nice stay"
United States
Danelle B.
$172 nightly
The price is $197
Aug 26 - Aug 27
Total with taxes and fees
Historic Haven in Church Hill in The Heart of the Historic District
A living room with two beige armchairs, a small table, and a black door.

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

Cozy Bungalow | 3 Parking Spots | Fully Fenced Yard
Richmond
10.0 out of 10, Exceptional, (8 reviews)
"The place was very nice and as advertised. Big backyard for your dog."
United States
Joseph
$256 nightly
The price is $281
Aug 30 - Aug 31
Total with taxes and fees
Cozy Bungalow | 3 Parking Spots | Fully Fenced Yard
A neatly made bed with a headboard, a bedside table with a lamp, a small bench, and a view through a window with a frosted glass panel.

18. 2 Rooms -2 Queen Beds Apartment in pleasant Richmond with AC, WiFi

2 Rooms -2 Queen Beds Apartment in pleasant Richmond with AC, WiFi
Fan District
9.8 out of 10, Exceptional, (32 reviews)
"Clean, great location, responsive host"
United States
Jim K.
$248 nightly
The price is $283
Sep 2 - Sep 3
Total with taxes and fees
2 Rooms -2 Queen Beds Apartment in pleasant Richmond with AC, WiFi
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.

19. 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.
$254 nightly
The price is $278
Aug 25 - Aug 26
Total with taxes and fees
Carytown Home/Free Parking/Fenced Yard/Family-Friendly/4TVs

20. Oaks Retreat Carytown House: Family & Pet Friendly

Oaks Retreat Carytown House: Family & Pet Friendly
Randolph
9.0 out of 10, Wonderful, (18 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.
$255 nightly
The price is $279
Aug 31 - Sep 1
Total with taxes and fees
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 Southside Hotel Reviews

The Commonwealth

The Commonwealth

10/10 Excellent
"Staff was great"
Caroline 2-night trip
Posted 1 hour ago
The Commonwealth

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 $183 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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