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
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Southside vacation rentals

Smart TV, fireplace, computer monitors

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
9.8 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.
$280 nightly
The price is $323
Aug 14 - Aug 15
Total with taxes and fees
Charming 1-bedroom suite with WiFi and AC in Bon Air
Living area

2. Renovated Modern Stylish “Vibrant” 4bdrm Home

Renovated Modern Stylish “Vibrant” 4bdrm Home
Beaufont
9.4 out of 10, Exceptional, (9 reviews)
"The overall experience was nice. Everything was there as advertised, and we would definitely stay there again"
United States
Johnny W.
$733 nightly
The price is $838
Aug 9 - Aug 10
Total with taxes and fees
Renovated Modern Stylish “Vibrant” 4bdrm Home
Smart TV

3. 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, (5 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.
$381 nightly
The price is $436
Sep 1 - Sep 2
Total with taxes and fees
Charming 3-bedroom townhome with WiFi in delightful Richmond
Exterior

4. The Enchanted Studio

The Enchanted Studio
Huguenot
10.0 out of 10, Exceptional, (1 review)
"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.
$254 nightly
The price is $288
Aug 9 - Aug 10
Total with taxes and fees
The Enchanted Studio
Smart TV, fireplace

5. The Birdhouse - Cozy Cottage Retreat in Richmond

The Birdhouse - Cozy Cottage Retreat in Richmond
Swansboro West
10.0 out of 10, Exceptional, (4 reviews)
"The BirdHouse is such a comfortable place. We loved the uniqueness and the little touches that mean alot on the road. We hope to stay again sometime."
United States
paula S.
$205 nightly
The price is $208
Aug 12 - Aug 13
Total with taxes and fees
The Birdhouse - Cozy Cottage Retreat in Richmond
Terrace/patio

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, (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.
$319 nightly
The price is $365
Aug 25 - Aug 26
Total with taxes and fees
Private Garden Home w/ Large Fenced Yard + Gazebo
Exterior

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
Aug 11 - Aug 12
Total with taxes and fees
The Lily Pad RVA- Charming Hidden Gem in the Southside of Richmond, Va.
Front of property

8. Cookie B

Cookie B
3.0 star property
Richmond
9.6 out of 10, Exceptional, (8 reviews)
"Was fantastic. Watching the sunrise was so memorable, captain ron was so friendly and stayed in communication well. will visit again. "
United States
Reshelle
$257 nightly
The price is $293
Sep 3 - Sep 4
Total with taxes and fees
Cookie B
View from property

9. MV GiaMaria

MV GiaMaria
3.5 star property
Richmond
9.2 out of 10, Wonderful, (16 reviews)
"So much fun!! Excellent host! Very informative. Loved the privacy and being on the water. The bed was super comfortable and the fireplace (electric) kept us warm and cozy. It was such a unique thing to do and we will be back!"
United States
Jane
$239 nightly
The price is $273
Sep 3 - Sep 4
Total with taxes and fees
MV GiaMaria
Marina

10. A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city

A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
Richmond
9.4 out of 10, Exceptional, (242 reviews)
"Peaceful, welcoming and inviting all describe our stay. I would highly recommend this houseboat for your visit to Richmond."
United States
FARYL H.
$186 nightly
The price is $213
Aug 9 - Aug 10
Total with taxes and fees
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
TV

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)
"Clean area, very easy to get in and out of, and great "
United States
Ryanne T.
$332 nightly
The price is $355
Aug 10 - Aug 11
Total with taxes and fees
Lovely 2 Bedroom in the Heart of The Fan
Coffee/tea maker, fridge, microwave, oven

12. 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, (75 reviews)
"Nice stay"
United States
Danelle B.
$170 nightly
The price is $194
Aug 11 - Aug 12
Total with taxes and fees
Historic Haven in Church Hill in The Heart of the Historic District
Smart TV, fireplace, books

13. 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.
$478 nightly
The price is $546
Aug 9 - Aug 10
Total with taxes and fees
Charming Historic Home-Walk to Carytown-Fence-Pet Friendly-Hotel-grade Towels
Coffee/tea maker, fridge, microwave, oven

14. 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, (91 reviews)
"Great option and neighborhood- enjoyed the stay"
United States
Gary P.
$160 nightly
The price is $183
Aug 11 - Aug 12
Total with taxes and fees
The Studio@ Eanes Drug-Heart of the Historic District
Dining

15. 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, (88 reviews)
"Clean, new, perfect location and a great host."
United States
Kyle P.
Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!
TV

16. Farmhouse Boho Retreat Peaceful 2 BR w/ Porch and Fenced Backyard

Farmhouse Boho Retreat Peaceful 2 BR w/ Porch and Fenced Backyard
Malvern Gardens
9.8 out of 10, Exceptional, (6 reviews)
"We enjoyed it. Nice place. "
United States
Suzannah W.
$252 nightly
The price is $288
Aug 10 - Aug 11
Total with taxes and fees
Farmhouse Boho Retreat Peaceful 2 BR w/ Porch and Fenced Backyard
TV, books, offices

17. Oaks Retreat Carytown House: Family & Pet Friendly

Oaks Retreat Carytown House: Family & Pet Friendly
Randolph
9.2 out of 10, Wonderful, (17 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.
$252 nightly
The price is $276
Aug 10 - Aug 11
Total with taxes and fees
Oaks Retreat Carytown House: Family & Pet Friendly
Exterior detail

18. Vincent House - Historic Charm & Modern Comfort

Vincent House - Historic Charm & Modern Comfort
Midlothian
9.8 out of 10, Exceptional, (8 reviews)
"This vintage home was the perfect place for our stay. It was very clean, had everything we needed, and the location near the wedding venue couldn’t have been better."
United States
Sandy
$591 nightly
The price is $680
Aug 9 - Aug 10
Total with taxes and fees
Vincent House - Historic Charm & Modern Comfort
Exterior detail

19. 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.
$453 nightly
The price is $517
Sep 7 - Sep 8
Total with taxes and fees
Charming Fan District Getaway
Interior

20. 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.
$262 nightly
The price is $288
Aug 10 - Aug 11
Total with taxes and fees
Carytown Home/Free Parking/Fenced Yard/Family-Friendly/4TVs
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

Quirk Hotel Richmond

Quirk Hotel Richmond

10/10 Excellent
"Lovely stay, thank you."
Patricia 1-night trip
Posted 3 hours ago
Quirk Hotel Richmond

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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