Photo by Nick Pagano

Search Vacation Homes in Chesterfield

Plan, book, stay with confidence

Be picky

Search almost a million properties worldwide

Treat yourself

Change your mind

Book hotels with free cancellation

Check prices for these dates

Next weekend

28 Saf. - 2 Rab. I

In two weeks

7 Rab. I - 9 Rab. I

In one month

21 Rab. I - 23 Rab. I

In two months

18 Rab. II - 20 Rab. II

Compare 274 Vacation Homes in Chesterfield with updated reviews, rates, and availability.

"A lovely house for a group of 5 girlfriends on a getaway weekend. It was warm and cozy with plenty of charm. Parking was easy and street was quiet. We loved it. "

Pool Opens in May, but trust us, the backyard is just as welcoming in the fall/winter/early spring

"We really enjoyed the pool table. The kitchen was very ell equipped for cooking…with pots and pans and utensils…I liked that you had basic things for example, ketchup and mustard…pepper and salt ."

SAR 2,511 total

includes taxes & fees

3 Mar - 4 Mar

front side Spring 2023 driveway just off to right

"The house was comfortable, clean, fully stocked. It was located in a great neighborhood, quiet. It's easy to get around in Richmond, so this house worked well for our needs. Good host-responsive and communicative. "

"Cute house, nice place to stay after going to a concert in Richmond. Quiet neighborhood. Loved the flamingo outside "

SAR 1,036 total

includes taxes & fees

26 Feb - 27 Feb

Property has wrap around driveway with plenty of parking.

"The house was extremely clean and had everything needed and as described. Lisa was prompt and accomodating at every turn. Neighborhood was quiet and outdoor space was great...unfortunately we had alot of rain. If we visit family in the area again, we'll definitely re-book and build a fire. "

"It was just what we need. "

SAR 1,436 total

includes taxes & fees

17 Mar - 18 Mar

"This is a great location for family to get together in a lovely home where everyone can have privacy as well as be together. Great neighborhood, very quiet. We would stay again for sure! "

"It was a very quiet and peaceful stay warm and cozy"

SAR 1,089 total

includes taxes & fees

24 Feb - 25 Feb

"Cannot beat the location - so close to Cary St. with all the shops and eateries! Larger than we expected, comfortable and clean. Nicely appointed kitchen. Spacious bathroom. Bonus - super short walk to grocery and drug store. Great “home base” for a visit to Richmond."

SAR 817 total

includes taxes & fees

24 Feb - 25 Feb

"The duplex was perfect for two families that were attending a family event in the Richmond area. The duplex had everything you could need, it was easy to access and it was just as indicated in the VRBO listing."

SAR 4,857 total

includes taxes & fees

27 Feb - 28 Feb

"Great place to get together with family, some of whom live in Richmond, some from out of town. Off-street parking was great. Kitchen was well-furnished, and the fridge is huge! Nice easy walks to the parks made this a great location."

"I had a poor experience with VRBO and this owner. My stay included being canceled on the day of."

"This house was exactly what we needed to hang out and rest up!"

Richmond Vacation Rental | 5BR | 3BA | 2,300 Sq Ft | Stairs Required

"Our extended family of all ages plus one small dog greatly enjoyed our stay in this home! Plenty of space for everyone to sleep, extra bathrooms, and a functional kitchen. The fenced-in back yard is perfect for pets and children. Street parking was easy and a nice playground at the end of the block and a small store a few blocks over were nice to have nearby. We would stay here again!"

"Great property manager, great communication! Property is clean and accommodating (especially for my mom who uses a wheelchair/walker due to bad knees. Only downside is the neighborhood was a little questionable… my mom heard what sounded like gunshots going off 2/3 nights she stayed. However, nothing else scary or questionable went on. So could have been a fluke! Overall, it’s a good place to stay for the price! "

SAR 768 total

includes taxes & fees

25 Feb - 26 Feb

Richmond Vacation Rental | 3BR | 2BA | 1,081 Sq Ft | Stairs Required

"Property was clean and comfortable. We spent a lot of time on property just visiting and this was the perfect place for this. "

"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. "

"Clean, well stocked, roomy"

Save an average of 15% on thousands of hotels when you're signed in

Other property types in Chesterfield

" Close to everything I needed. Staff was so nice and accommodating. Bed was so comfortable and room very clean. I enjoyed the whole happy hour experience. Breakfast was good. Definitely recommend and will be back for another stay!! "

SAR 549 total

includes taxes & fees

2 Mar - 3 Mar