Photo by Nick Pagano

Search Vacation Homes in Chesterfield

    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
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 338 Vacation Homes in Chesterfield with updated reviews, rates, and availability.

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

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
Amazing Private House Rental w/ pool! Richmond, VA
Exterior

Amazing Private House Rental w/ pool! Richmond, VA

9.0 out of 10, Wonderful, (59)
"Atmosphere was nice, place was clean, very clean"
The price is AED 551
AED 799 total
includes taxes & fees
7 May - 8 May
Amazing Private House Rental w/ pool! Richmond, VA
Great Location. Close to about everywhere .Can't beat the value. Check reviews!
Property grounds

Great Location. Close to about everywhere .Can't beat the value. Check reviews!

10.0 out of 10, Exceptional, (201)
"Great location, many amenities, I felt like I was in my own kitchen with all the utensils/supplies. Made our stay very enjoyable. "
Great Location. Close to about everywhere .Can't beat the value. Check reviews!
Cozy retreat just 1 mile from the Fine Creek Brewery & eclectic wedding venue.
Terrace/patio

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

10.0 out of 10, Exceptional, (35)
"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.
Gorgeously Renovated 3500 square foot Oxford home in Richmond!!
Smart TV

Gorgeously Renovated 3500 square foot Oxford home in Richmond!!

10.0 out of 10, Exceptional, (28)
"We thoroughly enjoyed our stay in this spacious and clean home. The children had plenty of room to play and the adults had a great t"
Gorgeously Renovated 3500 square foot Oxford home in Richmond!!
VMFA • Carytown • Keyless • Coffee & Treats • Queen Bedrooms • Generous Deck
Pool

VMFA • Carytown • Keyless • Coffee & Treats • Queen Bedrooms • Generous Deck

10.0 out of 10, Exceptional, (114)
"This is the second time that we rented Lynley’s place. We love it. It is so cozy and quiet, yet perfectly located for all that Richmond has to offer."
VMFA • Carytown • Keyless • Coffee & Treats • Queen Bedrooms • Generous Deck
The Greenwood, a modern barndominium. Cozy, spacious, and private
Living area

The Greenwood, a modern barndominium. Cozy, spacious, and private

10.0 out of 10, Exceptional, (2)
"Great place. Clean. Really comfortable couch. Jen was super responsive and easy to work with"
The Greenwood, a modern barndominium. Cozy, spacious, and private
Cozy walkable downtown retreat, 3 minutes to VCU
Exterior detail

Cozy walkable downtown retreat, 3 minutes to VCU

9.4 out of 10, Exceptional, (13)
"We had a fabulous stay celebrating Christmas with family in Richmond. "
The price is AED 393
AED 1,655 total
includes taxes & fees
18 May - 19 May
Cozy walkable downtown retreat, 3 minutes to VCU
Historic Modern Walkable to to VCU
Private kitchen

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 1,711 total
includes taxes & fees
21 May - 22 May
Historic Modern Walkable to to VCU
NOLA Happy Home Central location w/ large fenced yard FIRE-PIT
Outdoor dining

NOLA Happy Home Central location w/ large fenced yard FIRE-PIT

9.6 out of 10, Exceptional, (40)
"Great house with all the amenities needed. Central location in town, easily travel to surrounding destinations via Uber or car. Check out was easy and quick"
The price is AED 463
AED 1,046 total
includes taxes & fees
21 May - 22 May
NOLA Happy Home Central location w/ large fenced yard FIRE-PIT
Charming, Cheerful 3 Bedroom Home in Richmond, VA!
Fridge, microwave, oven, stovetop

Charming, Cheerful 3 Bedroom Home in Richmond, VA!

9.8 out of 10, Exceptional, (18)
"Property was clean and host was very accessible to communicate with during our stay."
Charming, Cheerful 3 Bedroom Home in Richmond, VA!
Stylish retreat in charming Richmond with Private Sauna and other modern touches
Fridge, microwave, oven, stovetop

Stylish retreat in charming Richmond with Private Sauna and other modern touches

10.0 out of 10, Exceptional, (3)
"The house was cute and cozy in a nice and quiet neighborhood. "
Stylish retreat in charming Richmond with Private Sauna and other modern touches
Central RVA Home: 4 Bed, 3 Bath Getaway!
Interior

Central RVA Home: 4 Bed, 3 Bath Getaway!

10.0 out of 10, Exceptional, (1)
Central RVA Home: 4 Bed, 3 Bath Getaway!
Heart of the Fan: 2BR/2BA Strawberry Street Stay
Hair dryer, towels

Heart of the Fan: 2BR/2BA Strawberry Street Stay

10.0 out of 10, Exceptional, (1)
"We absolutely loved this property. Clean, Comfortable, and Convenient!! The kitchen and bathrooms are stocked with everything needed. The bedding and all furniture were comfortable. Everything was very clean.The area has great restaurants and shops in walking distance - as well as VMFA.Lovely place - we will be staying there again!!"
The price is AED 656
AED 1,476 total
includes taxes & fees
11 May - 12 May
Heart of the Fan: 2BR/2BA Strawberry Street Stay
Church Hill • Fenced • Pet Friendly • One Level • King Suite + 2 Queen Bedrooms
3 bedrooms, iron/ironing board, WiFi, bed sheets

Church Hill • Fenced • Pet Friendly • One Level • King Suite + 2 Queen Bedrooms

10.0 out of 10, Exceptional, (7)
"Very nice well decorated property manager extremely responsive. Looking forward to staying again. Highly recommend!"
Church Hill • Fenced • Pet Friendly • One Level • King Suite + 2 Queen Bedrooms
In the Village Of Powhatan- walking distance to owners restaurant
5 bedrooms, desk, iron/ironing board, travel crib

In the Village Of Powhatan- walking distance to owners restaurant

10.0 out of 10, Exceptional, (38)
"Had an Awesome time"
In the Village Of Powhatan- walking distance to owners restaurant
Recline at Timberline! Family friendly!
Fridge, microwave, oven, stovetop

Recline at Timberline! Family friendly!

9.4 out of 10, Exceptional, (42)
"Would not stay here again. The house is roach infested. "
Recline at Timberline! Family friendly!
Versatile RVA Oasis on Monument Ave
Outdoor dining

Versatile RVA Oasis on Monument Ave

10.0 out of 10, Exceptional, (12)
"Property was so relaxing after a day exploring Richmond. Our host was great and very responsive. Hope we can stay again when we can enjoy the pool."
Versatile RVA Oasis on Monument Ave
Charming 3-bedroom townhome with WiFi in delightful Richmond
Smart TV

Charming 3-bedroom townhome with WiFi in delightful Richmond

10.0 out of 10, Exceptional, (2)
"Townhouse was awesome. Plenty of room for 6 people. Pet friendly. Quiet neighborhood. Host Jordan was very helpful and available when needed. We all loved our stay. Would stay again. "
The price is AED 489
AED 1,246 total
includes taxes & fees
14 May - 15 May
Charming 3-bedroom townhome with WiFi in delightful Richmond
Welcome to King George Manor your family-friendly getaway!
Fridge, microwave, oven, stovetop

Welcome to King George Manor your family-friendly getaway!

9.8 out of 10, Exceptional, (7)
"House was clean and well set up for family quality time."
Welcome to King George Manor your family-friendly getaway!
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.
Don't see what you're looking for?
See all available properties in Chesterfield
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Chesterfield

Barsala At Sphere Apartments
Interior

Barsala At Sphere Apartments

3.5 star property
9.2 out of 10, Wonderful, (11)
"The neighborhood was quiet and it has nice food places around "
Barsala At Sphere Apartments
Tourist Homes of Richmond Church Hill North
Toaster, cleaning supplies, paper towels

Tourist Homes of Richmond Church Hill North

4.0 star property
8.0 out of 10, Very Good, (11)
"Excellent communication with the landlord and perfectly quiet and clean"
Tourist Homes of Richmond Church Hill North
Lovely 2 Bedroom in the Heart of The Fan
Fridge, microwave, oven, stovetop

Lovely 2 Bedroom in the Heart of The Fan

9.4 out of 10, Exceptional, (55)
"My daughter and I stayed here for a work weekend. My daughter attended the VRLR on the Hill event and had an awesome time. We loved the location and spaciousness of the apartment."
The price is AED 498
AED 1,123 total
includes taxes & fees
12 May - 13 May
Lovely 2 Bedroom in the Heart of The Fan
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.