Search Vacation Homes in Southside

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 343 Vacation Homes in Southside with updated reviews, rates, and availability.

Cozy retreat just 1 mile from the Fine Creek Brewery & eclectic wedding venue.

10.0 out of 10, Exceptional, (36)
"We had a wonderful stay. The place is just as advertised and meticulously kept. We enjoyed the quite surroundings and highly recommend."
Cozy retreat just 1 mile from the Fine Creek Brewery & eclectic wedding venue.

Charming, Cheerful 3 Bedroom Home in Richmond, VA!

9.8 out of 10, Exceptional, (20)
"Property was clean and host was very accessible to communicate with during our stay."
Charming, Cheerful 3 Bedroom Home in Richmond, VA!

Amazing Private House Rental w/ pool! Richmond, VA

9.0 out of 10, Wonderful, (62)
"Atmosphere was nice, place was clean, very clean"
The price is AED 918
AED 1,340 total
includes taxes & fees
3 Jun - 4 Jun
Amazing Private House Rental w/ pool! Richmond, VA

Clean, Quiet, & Cozy Ashland Home

9.8 out of 10, Exceptional, (38)
"Perfect for a family stay"
The price is AED 680
AED 1,340 total
includes taxes & fees
29 May - 30 May
Clean, Quiet, & Cozy Ashland Home

The Cozy Rancher | Petersburg | King Bed

10.0 out of 10, Exceptional, (29)
"This was a perfect spot for our short weekend trip down to Richmond for the marathon!"
The price is AED 569
AED 1,355 total
includes taxes & fees
1 Jun - 2 Jun
The Cozy Rancher | Petersburg | King Bed

Richmond Oasis: Your Home Away from Home in the Heart of the City

7.8 out of 10, Good, (8)
"Went to this location for a short stay and definitely surprised me with the size. Would definitely visit again."
Richmond Oasis: Your Home Away from Home in the Heart of the City

Richmond Gem, Free Parking, Quiet, Fenced,Walkable

10.0 out of 10, Exceptional, (14)
"Wonderful stay… beautifully decorated… nice and bright, clean. Lots of wonderful details. Will definitely come back!!"
The price is AED 1,102
AED 2,157 total
includes taxes & fees
29 May - 30 May
Richmond Gem, Free Parking, Quiet, Fenced,Walkable

Spacious 5-bedroom house with AC and WiFi in delightful Mechanicsville

8.8 out of 10, Excellent, (3)
"The property owner was kind and very responsive. Would stay again"
Spacious 5-bedroom house with AC and WiFi in delightful Mechanicsville

Grand Carytown family home 6BR FREE parking

2.0 star property
10.0 out of 10, Exceptional, (1)
"Don’t just look book lol, we enjoyed our stay will stay again"
The price is AED 1,168
AED 2,344 total
includes taxes & fees
9 Jun - 10 Jun
Grand Carytown family home 6BR FREE parking

NEW! Upscale Escape | Game Room & Spa-Like Baths

10.0 out of 10, Exceptional, (1)
"We enjoyed our stay here with family. The home is beautiful and welcoming! "
NEW! Upscale Escape | Game Room & Spa-Like Baths

Charming 1940s Vintage Home in Hanover County

10.0 out of 10, Exceptional, (1)
"Most place skimp on the beds and bedding but this place doesn't. I get a VRBO about 6 times a year and wish they were all like this one."
The price is AED 1,286
AED 2,384 total
includes taxes & fees
29 May - 30 May
Charming 1940s Vintage Home in Hanover County

Bugalow near Airport - Private Yard, Close to City

2.0 star property
10.0 out of 10, Exceptional, (6)
"Great little house. Very clean, and had everything that we needed. Host was very responsive and helpful in finding things to do, and where to eat. Would definitely stay here again. "
The price is AED 588
AED 798 total
includes taxes & fees
29 May - 30 May
Bugalow near Airport - Private Yard, Close to City

The Henrico Hideaway: Firepit, Close to Everything

10.0 out of 10, Exceptional, (4)
"This house was perfect for what we needed! The beds were comfy (the master was my fave!) Communication with the host was great! Very timely. Great experience overall. "
The Henrico Hideaway: Firepit, Close to Everything

Historic Modern Walkable to to VCU

2.0 star property
8.8 out of 10, Excellent, (3)
"Big clean home with lots of room!"
The price is AED 422
AED 1,721 total
includes taxes & fees
29 May - 30 May
Historic Modern Walkable to to VCU

The Bamboo House! Dog-Friendly Home n RVA Sleeps 8

9.2 out of 10, Wonderful, (23)
"James’s house was warm, inviting and clean - something you don’t often see in a dog friendly rental! The kitchen is well appointed and well stocked, and we had everything we needed for a lovely family get together that included baking, movie watching and playing with the dogs in a safe, enclosed yard. Thank you, James, for a delightful stay. We will be back!!"
The Bamboo House! Dog-Friendly Home n RVA Sleeps 8

Cottage on Capital Trail | 2BR | Incredible Views

9.6 out of 10, Exceptional, (5)
"Seems like some VRBO hosts are omitting everything possible, like moving into a shell of a home. Not this one! Our host was considerate like you'd expect a proper hotel should be -- no need to run around to a store to pick up a little shampoo if you forgot it. Extremely communicative from the moment we booked, which was another above and beyond aspect."
The price is AED 501
AED 1,329 total
includes taxes & fees
3 Jun - 4 Jun
Cottage on Capital Trail | 2BR | Incredible Views

Peaceful Single family 3 Bedroom 2 Bath Home

8.6 out of 10, Excellent, (20)
"Was a great house to stay at. They accommodated my family well with my 3 dogs. Had a nice fenced-in back yard and plenty of space in the house for my family. Owner communicated with me well. I would recommend this VRBO for family too use. "
Peaceful Single family 3 Bedroom 2 Bath Home

Historic Petersburg Row Home

10.0 out of 10, Exceptional, (12)
"Nice location, beautiful home!"
Historic Petersburg Row Home

The Great Pink Lady with Huge Wrap Around Porch!

8.4 out of 10, Very Good, (7)
"As the title says, this place looked like the photos and was in a cute neighborhood that was pretty quiet. Good communication, no complaints!"
The Great Pink Lady with Huge Wrap Around Porch!

VCU • Fenced • Pet Friendly • Keyless • King Suite + 2 Queen Bedrooms

9.8 out of 10, Exceptional, (116)
"Perfect location for museum hopping and good food. It’s so well decorated and comfortable. Thank you for being a super host. We would like to book again in the future. "
VCU • Fenced • Pet Friendly • Keyless • King Suite + 2 Queen Bedrooms
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.
Save an average of 15% on thousands of hotels when you're signed in