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Chesterfield Vacation Rentals

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Check prices for these dates

Next weekend
Aug 8 - Aug 10
In two weeks
Aug 15 - Aug 17
In one month
Aug 29 - Aug 31
In two months
Sep 26 - Sep 28

Browse Select Chesterfield Vacation Homes

Cozy retreat just 1 mile from the Fine Creek Brewery & eclectic wedding venue.
Relax in a serene outdoor space with Adirondack chairs, fire pit, and grill.

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

10.0 out of 10, Exceptional, (46)
"Fantastic place"
Cozy retreat just 1 mile from the Fine Creek Brewery & eclectic wedding venue.
Cozy walkable downtown retreat, 3 minutes to VCU
Traditional brick building with a charming yellow door and classic white columns, set amidst a beautifully maintained garden with gravel pathways.

Cozy walkable downtown retreat, 3 minutes to VCU

9.4 out of 10, Exceptional, (14)
"Great stay."
The price is CA $172
CA $662 total
includes taxes & fees
Aug 11 - Aug 12
Cozy walkable downtown retreat, 3 minutes to VCU
Bugalow near Airport - Private Yard, Close to City
Enjoy cooking in this well-equipped kitchen with appliances and a convenient dining area.

Bugalow near Airport - Private Yard, Close to City

2.0 star property
10.0 out of 10, Exceptional, (11)
"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. "
Bugalow near Airport - Private Yard, Close to City
The Cozy Rancher | Petersburg | King Bed
Relax in this serene bedroom with a large bed, bedside tables, and a ceiling fan.

The Cozy Rancher | Petersburg | King Bed

10.0 out of 10, Exceptional, (31)
"It was a great experience and the house was lovely and just like the pictures ."
The price is CA $192
CA $481 total
includes taxes & fees
Aug 3 - Aug 4
The Cozy Rancher | Petersburg | King Bed
Richmond Area Home w/ Game Room & Patio!
Enjoy cooking in this well-equipped kitchen with a dishwasher, microwave, oven, and refrigerator.

Richmond Area Home w/ Game Room & Patio!

9.8 out of 10, Exceptional, (19)
"The property is just as listed, if not better! Clean House, Easy Check In, Great Location, everything was great!!!"
Richmond Area Home w/ Game Room & Patio!
Charming 1-bedroom suite with WiFi and AC in Bon Air
Relax in this stylish living space, featuring a large chandelier, flat-screen TV, and comfortable sectional sofa.

Charming 1-bedroom suite with WiFi and AC in Bon Air

10.0 out of 10, Exceptional, (4)
"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 "
The price is CA $131
CA $273 total
includes taxes & fees
Aug 25 - Aug 26
Charming 1-bedroom suite with WiFi and AC in Bon Air
Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!
Enjoy a spacious living area with a sofa and coffee table, a kitchen with stainless steel appliances, and a large window offering a view of the outdoors.

Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!

9.8 out of 10, Exceptional, (66)
"Clean, nicely decorated apartment convenient to downtown RVA."
The price is CA $149
CA $332 total
includes taxes & fees
Aug 6 - Aug 7
Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!
The Henrico Hideaway: Firepit, Close to Everything
Enjoy casual dining at the central island with bar stools, surrounded by sleek cabinetry and stainless steel appliances.

The Henrico Hideaway: Firepit, Close to Everything

10.0 out of 10, Exceptional, (7)
"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
In the Village Of Powhatan- walking distance to owners restaurant
Relax in this charming attic bedroom with a large bed, a smaller bed, and a cozy seating area.

In the Village Of Powhatan- walking distance to owners restaurant

10.0 out of 10, Exceptional, (42)
"Quite comfortable and centrally located"
In the Village Of Powhatan- walking distance to owners restaurant
Private House in Heart of Historic Barton Heights!
Fridge, microwave, oven, stovetop

Private House in Heart of Historic Barton Heights!

9.8 out of 10, Exceptional, (8)
"Very nice, clean house. Enjoyed our stay and had no issues!"
Private House in Heart of Historic Barton Heights!
Stylish retreat in charming Richmond with Private Sauna and other modern touches
Enjoy cooking in this well-equipped kitchen with a TV, farmhouse-style cabinetry, and stainless steel appliances.

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

9.8 out of 10, Exceptional, (11)
"The house was cute and cozy in a nice and quiet neighborhood. "
Stylish retreat in charming Richmond with Private Sauna and other modern touches
Nice! New home near VSU x Fort Gregg Adams Military Base mins to DT Richmond VA
Enjoy a spacious living area with a kitchen and seating space, featuring a sofa, coffee table, and plant.

Nice! New home near VSU x Fort Gregg Adams Military Base mins to DT Richmond VA

10.0 out of 10, Exceptional, (15)
"Great place and host enjoyed everything "
Nice! New home near VSU x Fort Gregg Adams Military Base mins to DT Richmond VA
~THE RETREAT~
Relax by the pool surrounded by a deck with lounge chairs and a gazebo.

~THE RETREAT~

9.8 out of 10, Exceptional, (22)
"Great time"
~THE RETREAT~
Amazing Private House Rental w/ pool! Richmond, VA
Experience the charm of historic St. Richmond at BLIM, a distinctive building with a central tower and turret.

Amazing Private House Rental w/ pool! Richmond, VA

9.0 out of 10, Wonderful, (64)
"This place was awesome I love the fact that she allowed party’s, also like we were able to have a designated smoking area, although from the outside it looks really small but once inside it was so big, back yard was very nice we will return! "
The price is CA $345
CA $662 total
includes taxes & fees
Aug 19 - Aug 20
Amazing Private House Rental w/ pool! Richmond, VA
Enjoy Breezes on the James River, 2bdrm-1bath / 15 minutes to downtown Richmond
Experience the tranquility of this riverside retreat, surrounded by lush greenery and a well-maintained lawn, with a kayak available for guests to enjoy.

Enjoy Breezes on the James River, 2bdrm-1bath / 15 minutes to downtown Richmond

9.8 out of 10, Exceptional, (178)
"We spent a relaxing lovely long weekend next to the James River. It was beautiful and the bonus of the horses & donkey next door was amazing! "
Enjoy Breezes on the James River, 2bdrm-1bath / 15 minutes to downtown Richmond
Urban Hearth in Carytown/fenced yard/free parking
Relax in a charming outdoor seating area with wicker furniture and lush greenery.

Urban Hearth in Carytown/fenced yard/free parking

9.4 out of 10, Exceptional, (3)
"Nice place and convenient location"
The price is CA $187
CA $410 total
includes taxes & fees
Aug 26 - Aug 27
Urban Hearth in Carytown/fenced yard/free parking
Great Location. Close to about everywhere .Can't beat the value. Check reviews!
Stroll along the beautifully maintained garden pathway to a charming building with a classic facade, featuring evenly spaced windows and shutters.

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

10.0 out of 10, Exceptional, (212)
"Josh's house was perfect for our family stay in Richmond for our daughter's wedding. Josh is a great host, the house was clean and comfortable with everything we needed."
Great Location. Close to about everywhere .Can't beat the value. Check reviews!
Richmond Home w/ Fire Pit - 12 Mi to Downtown
Enjoy cooking in this well-equipped kitchen with a stainless steel oven, microwave, and refrigerator.

Richmond Home w/ Fire Pit - 12 Mi to Downtown

9.8 out of 10, Exceptional, (27)
"It was fabulous. We had a great time sight seeing a great getaway for spring break "
Richmond Home w/ Fire Pit - 12 Mi to Downtown
Erin's Oasis in Richmond
Stroll through this serene garden oasis, surrounded by lush greenery and a tranquil statue.

Erin's Oasis in Richmond

9.8 out of 10, Exceptional, (54)
"wonderful property"
Erin's Oasis in Richmond
Charming 2-bedroom house with WiFi, AC, & Patio in the heart of Richmond!
Enjoy meals around the central island in this kitchen, featuring a stainless steel refrigerator, microwave, and oven.

Charming 2-bedroom house with WiFi, AC, & Patio in the heart of Richmond!

10.0 out of 10, Exceptional, (3)
"This place was just perfect for our stay. Beautiful historic home, plenty of room, great kitchen. We just loved it. Would come back and stay again and again!"
The price is CA $159
CA $412 total
includes taxes & fees
Aug 6 - Aug 7
Charming 2-bedroom house with WiFi, AC, & Patio in the heart of Richmond!
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 Chesterfield Hotel Reviews

Regency Inn Richmond

Regency Inn Richmond

10/10 Excellent
"Management was excellent the bed was so comfortable "
Miranda 1-night trip
Posted 12 hours ago
Regency Inn Richmond