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 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Southside vacation rentals

Smart TV, fireplace

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.
$200 nightly
The price is $203
Aug 20 - Aug 21
Total with taxes and fees
The Birdhouse - Cozy Cottage Retreat in Richmond
Smart TV

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.
$355 nightly
The price is $406
Sep 2 - Sep 3
Total with taxes and fees
Charming 3-bedroom townhome with WiFi in delightful Richmond
Smart TV, fireplace, computer monitors

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
9.8 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 20 - Aug 21
Total with taxes and fees
Charming 1-bedroom suite with WiFi and AC in Bon Air
Terrace/patio

4. 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.
$299 nightly
The price is $342
Aug 25 - Aug 26
Total with taxes and fees
Private Garden Home w/ Large Fenced Yard + Gazebo
Exterior

5. 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.
$200 nightly
The price is $227
Aug 23 - Aug 24
Total with taxes and fees
The Enchanted Studio
Living area

6. 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 20 - Aug 21
Total with taxes and fees
Renovated Modern Stylish “Vibrant” 4bdrm Home
Dining

7. Carytown cozy nest private room Fenced Yard

Carytown cozy nest private room Fenced Yard
Carytown
9.8 out of 10, Exceptional, (31 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.
$123 nightly
The price is $137
Aug 20 - Aug 21
Total with taxes and fees
Carytown cozy nest private room Fenced Yard
TV

8. 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.
$360 nightly
The price is $385
Aug 21 - Aug 22
Total with taxes and fees
Lovely 2 Bedroom in the Heart of The Fan
1 bedroom, desk, iron/ironing board, WiFi

9. 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.
$206 nightly
The price is $235
Sep 8 - Sep 9
Total with taxes and fees
Private Guest house with Parking and Wi-Fi in a Central Location
Coffee/tea maker, fridge, microwave, oven

10. 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 20 - Aug 21
Total with taxes and fees
The Studio@ Eanes Drug-Heart of the Historic District
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.
$245 nightly
The price is $280
Aug 24 - Aug 25
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.
$193 nightly
The price is $221
Aug 20 - Aug 21
Total with taxes and fees
Colorful private guesthouse in charming Richmond with Parking
TV

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.
$225 nightly
The price is $257
Sep 1 - Sep 2
Total with taxes and fees
Apartment 2B Premium 1-bedroom and 1- Living Room in FAN Area Richmond
Coffee/tea maker, fridge, microwave, oven

14. 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.
$170 nightly
The price is $194
Aug 20 - Aug 21
Total with taxes and fees
Historic Haven in Church Hill in The Heart of the Historic District
Interior

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

Cozy Bungalow | 3 Parking Spots | Fully Fenced Yard
Richmond
10.0 out of 10, Exceptional, (7 reviews)
"Great location! Host responsive!"
United States
Rebekah G.
$246 nightly
The price is $269
Sep 1 - Sep 2
Total with taxes and fees
Cozy Bungalow | 3 Parking Spots | Fully Fenced Yard
TV, books, offices

16. 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.
$254 nightly
The price is $278
Sep 15 - Sep 16
Total with taxes and fees
Oaks Retreat Carytown House: Family & Pet Friendly
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.
$253 nightly
The price is $277
Sep 15 - Sep 16
Total with taxes and fees
Carytown Home/Free Parking/Fenced Yard/Family-Friendly/4TVs
1 bedroom, in-room safe, WiFi (free), bed sheets

18. Magnolias, a chill out place.

Magnolias, a chill out place.
Richmond
9.2 out of 10, Wonderful, (23 reviews)
"Would stay again!"
United States
Amir D.
$112 nightly
The price is $128
Sep 8 - Sep 9
Total with taxes and fees
Magnolias, a chill out place.
2 bedrooms, iron/ironing board, WiFi, bed sheets

19. 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
10.0 out of 10, Exceptional, (30 reviews)
"Clean, great location, responsive host"
United States
Jim K.
$270 nightly
The price is $309
Sep 1 - Sep 2
Total with taxes and fees
2 Rooms -2 Queen Beds Apartment in pleasant Richmond with AC, WiFi
TV

20. Modern Apartment- Walk to Convention Center- Deck- Off-Street Parking

Modern Apartment- Walk to Convention Center- Deck- Off-Street Parking
Downtown Richmond
9.0 out of 10, Wonderful, (7 reviews)
"Alex was super communicative and the apartment was exactly as advertised. Would absolutely recommend!"
United States
Nicholas S.
Modern Apartment- Walk to Convention Center- Deck- Off-Street 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

Best Western Plus Glen Allen Inn

Best Western Plus Glen Allen Inn

8/10 Good
"Like having the microwave and refrigerator. The pool was not clean."
Wayne 2-night trip
Posted less than an hour ago
Best Western Plus Glen Allen Inn

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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