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 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 Southside vacation rentals

Living area

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.
$203 nightly
The price is $206
Sep 3 - Sep 4
Total with taxes and fees
The Birdhouse - Cozy Cottage Retreat in Richmond
Living area

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.
$405 nightly
The price is $463
Sep 8 - Sep 9
Total with taxes and fees
Charming 3-bedroom townhome with WiFi in delightful Richmond
Living area

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
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.
$280 nightly
The price is $323
Sep 3 - Sep 4
Total with taxes and fees
Charming 1-bedroom suite with WiFi and AC in Bon Air
Exterior

4. 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.
$198 nightly
The price is $225
Sep 3 - Sep 4
Total with taxes and fees
The Enchanted Studio
Terrace/patio

5. 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.
$324 nightly
The price is $370
Sep 14 - Sep 15
Total with taxes and fees
Private Garden Home w/ Large Fenced Yard + Gazebo
Living area

6. 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
Sep 3 - Sep 4
Total with taxes and fees
Renovated Modern Stylish “Vibrant” 4bdrm Home
Room

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
$724 nightly
The price is $827
Sep 3 - Sep 4
Total with taxes and fees
The Lily Pad RVA- Charming Hidden Gem in the Southside of Richmond, Va.
Room

8. 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, (12 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.
$210 nightly
The price is $240
Sep 7 - Sep 8
Total with taxes and fees
Private Guest house with Parking and Wi-Fi in a Central Location
Living area

9. 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.
$332 nightly
The price is $355
Sep 21 - Sep 22
Total with taxes and fees
Lovely 2 Bedroom in the Heart of The Fan
Living area

10. 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.
$251 nightly
The price is $287
Sep 7 - Sep 8
Total with taxes and fees
Apartment 2B Premium 1-bedroom and 1- Living Room in FAN Area Richmond
Dining

11. 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
Sep 3 - Sep 4
Total with taxes and fees
Cozy 2-bedroom apartment in beautiful Fan District
Outdoor dining

12. 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.
$192 nightly
The price is $219
Sep 3 - Sep 4
Total with taxes and fees
Colorful private guesthouse in charming Richmond with Parking
Room

13. 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.
$251 nightly
The price is $287
Sep 14 - Sep 15
Total with taxes and fees
2 Rooms -2 Queen Beds Apartment in pleasant Richmond with AC, WiFi
Interior

14. 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
$242 nightly
The price is $264
Sep 7 - Sep 8
Total with taxes and fees
Cozy Bungalow | 3 Parking Spots | Fully Fenced Yard
Living area

15. 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.
$253 nightly
The price is $277
Sep 3 - Sep 4
Total with taxes and fees
Oaks Retreat Carytown House: Family & Pet Friendly
Private kitchen

16. 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, (94 reviews)
"Very clean, cozy and in an excellent location."
United States
Courtney W.
$165 nightly
The price is $189
Sep 3 - Sep 4
Total with taxes and fees
The Studio@ Eanes Drug-Heart of the Historic District
Interior

17. 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.
$252 nightly
The price is $276
Sep 3 - Sep 4
Total with taxes and fees
Carytown Home/Free Parking/Fenced Yard/Family-Friendly/4TVs
Private kitchen

18. 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.
$171 nightly
The price is $195
Sep 7 - Sep 8
Total with taxes and fees
Historic Haven in Church Hill in The Heart of the Historic District
Room

19. 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
Sep 9 - Sep 10
Total with taxes and fees
Magnolias, a chill out place.
Terrace/patio

20. 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.
$185 nightly
The price is $213
Sep 20 - Sep 21
Total with taxes and fees
Newly finished basement suite in Midlothian. Very clean and spacious.
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

Best Western PLUS Executive Hotel

Best Western PLUS Executive Hotel

10/10 Excellent
"z"
Jesus 3-night trip
Posted less than an hour ago
Best Western PLUS Executive Hotel

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 $189 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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