Chesterfield Holiday Rentals

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Our top choices for Chesterfield holiday rentals

Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.

Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.
Chesterfield
10.0 out of 10, Exceptional, (5 reviews)
"The location is beautiful! Kristina was very prompt in answering my questions and very accommodating. Wonderful stay."
United States
Connie D.
The price is AU$334
includes taxes & fees
15 June - 16 June
Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.

Qualla Park

Qualla Park
Chesterfield County
10.0 out of 10, Exceptional, (3 reviews)
"The home was beautiful and amazing! Host was amazing too! Highly recommend!"
United Kingdom
Shannon W.
The price is AU$606
includes taxes & fees
10 June - 11 June
Qualla Park

A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations

A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations
Richmond
9.6 out of 10, Exceptional, (119 reviews)
"Very nice stay! Awesome host and quiet neighborhood! Thank you!"
United States
Wes E.
The price is AU$301
includes taxes & fees
9 June - 10 June
A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations

A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city

A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
Richmond
9.4 out of 10, Exceptional, (236 reviews)
"Beautiful setting and comfortable accommodations. "
United States
deirdre b.
The price is AU$302
includes taxes & fees
15 June - 16 June
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city

Cookie B

Cookie B
3.0 star property
Richmond
9.6 out of 10, Exceptional, (8 reviews)
"Was fantastic. Watching the sunrise was so memorable, captain ron was so friendly and stayed in communication well. will visit again. "
United States
Reshelle
The price is AU$417
includes taxes & fees
5 June - 6 June
Cookie B

Luxury Stay! 10 min away from Fort Lee.

Luxury Stay! 10 min away from Fort Lee.
Prince George
8.4 out of 10, Very good, (17 reviews)
"The home was very clean and very comfortable. Communication was excellent. We would definitely stay here again!"
United States
CHRIS
The price is AU$566
includes taxes & fees
8 June - 9 June
Luxury Stay! 10 min away from Fort Lee.

The Birdhouse - Cozy Cottage Retreat in Richmond

The Birdhouse - Cozy Cottage Retreat in Richmond
Swansboro West
10.0 out of 10, Exceptional, (1 review)
"The most beautifully finished cottage! Host very responsive!! Loved it."
United States
Stephanie S.
The price is AU$275
includes taxes & fees
9 June - 10 June
The Birdhouse - Cozy Cottage Retreat in Richmond

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, (78 reviews)
"Room was wonderful, very clean & cozy. Great location!"
United States
Kirk
The price is AU$258
includes taxes & fees
7 June - 8 June
The Studio@ Eanes Drug-Heart of the Historic District

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, (84 reviews)
"Easy check in and a pleasant quick stay "
United States
Megan M.
The price is AU$500
includes taxes & fees
10 June - 11 June
Lovely 2 Bedroom in the Heart of The Fan

The Farmhouse Retreat

The Farmhouse Retreat
Mechanicsville
10.0 out of 10, Exceptional, (4 reviews)
"Nice place in the country. Tyler is an excellent host. "
United States
Tom C.
The price is AU$226
includes taxes & fees
21 June - 22 June
The Farmhouse Retreat

Carytown cozy nest private room Fenced Yard

Carytown cozy nest private room Fenced Yard
Carytown
9.8 out of 10, Exceptional, (28 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.
The price is AU$205
includes taxes & fees
7 June - 8 June
Carytown cozy nest private room Fenced Yard

Cozy Bungalow | 3 Parking Spots | Fully Fenced Yard

Cozy Bungalow | 3 Parking Spots | Fully Fenced Yard
Richmond
10.0 out of 10, Exceptional, (4 reviews)
"Great location! Host responsive!"
United States
Rebekah G.
The price is AU$411
includes taxes & fees
8 June - 9 June
Cozy Bungalow | 3 Parking Spots | Fully Fenced Yard

Cozy Blackstone Getaway < 2 Mi to Downtown!

Cozy Blackstone Getaway < 2 Mi to Downtown!
3.0 star property
Blackstone
10.0 out of 10, Exceptional, (1 review)
"Clean, comfortable place for 2-4 people. 4 might be pushing it with one bath. Ate at The Brew House and Mitchell’s and both were quite good."
United States
Richard
Cozy Blackstone Getaway < 2 Mi to Downtown!

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

Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!
Downtown Richmond
10.0 out of 10, Exceptional, (82 reviews)
"My fave place to stay! Great location and awesome set up! If i were a young guy getting out of school I would live there! Convenient to walk to many cool places too"
United States
rob
The price is AU$293
includes taxes & fees
8 June - 9 June
Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!

Cozy Bon Air Guest Suite with Private Entrance

Cozy Bon Air Guest Suite with Private Entrance
Bon Air
The price is AU$224
includes taxes & fees
30 June - 1 July
Cozy Bon Air Guest Suite with Private Entrance

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, (24 reviews)
"Great place to stay. I will be back"
United States
Bridgette T.
The price is AU$405
includes taxes & fees
9 June - 10 June
Apartment 2B Premium 1-bedroom and 1- Living Room in FAN Area Richmond

The Fan Comfort Stay near VCU Free Parking Fenced Yard

The Fan Comfort Stay near VCU Free Parking Fenced Yard
Fan District
9.6 out of 10, Exceptional, (28 reviews)
"Great location"
United States
Larry
The price is AU$283
includes taxes & fees
7 June - 8 June
The Fan Comfort Stay near VCU Free Parking Fenced Yard

Downtown Living in Richmond's Amazing Shockoe Bottom

Downtown Living in Richmond's Amazing Shockoe Bottom
Downtown Richmond
8.6 out of 10, Excellent, (34 reviews)
"Was I great place to stay! Very responsive and gave all the info you need to make the trip and stay easy! "
United States
Dillon D.
The price is AU$458
includes taxes & fees
8 June - 9 June
Downtown Living in Richmond's Amazing Shockoe Bottom

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
10.0 out of 10, Exceptional, (7 reviews)
"The place was very clean and easily accessible. The place is near I-64 and the railroad, but the noise wasn't enough to disturb our sleep. For us, the bed was very firm."
United States
Frank
The price is AU$357
includes taxes & fees
7 June - 8 June
Private Guest house with Parking and Wi-Fi in a Central Location

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, (5 reviews)
"Such a fun place to stay! Room is nicely decorated. Easy check in/check out. Never stayed in this part of RVA before. We will definitely stay here again!"
United States
Teresa M.
The price is AU$310
includes taxes & fees
10 June - 11 June
Colorful private guesthouse in charming Richmond with 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 Chesterfield Hotel Reviews

Find out more about Chesterfield

Everything you need to know about Chesterfield holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterfield holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 Chesterfield holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chesterfield holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesterfield. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesterfield holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesterfield holiday rentals we have selected for you start as low as AU$258 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chesterfield rentals

At Expedia, we put the best Chesterfield holiday 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 Chesterfield 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 Chesterfield holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesterfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Chesterfield?

Yes, there are holiday rentals close to the most popular sights in Chesterfield, or you can select a more secluded option if you're looking for a relaxing stay. Chesterfield is known for its shopping and golf courses. Make sure you have time to check out the parks and museums during your trip.

What are some of the best holiday rentals that Chesterfield has to offer?

Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!: This holiday home rental outside of Chesterfield has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals are there in Chesterfield?

Expedia has 6 holiday rentals for your stay in Chesterfield.

What can I see and do in Chesterfield?

While exploring the area, visit family-friendly sights like Iron Bridge Sports Park, or get outside and enjoy nature at Appomattox River. Magnolia Grange and Pocahontas State Park are other places to visit while you're in town.

What are holiday rentals like in Chesterfield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chesterfield. Holiday rentals offer extras such as patios, hot tubs and fire pits so you'll have all the conveniences of home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from shared hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for families.