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Chesterfield Holiday Rentals

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Holiday Rentals in Chesterfield

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

10.0 out of 10, Exceptional, (4)
"Visiting friends "
The price is AU$444
includes taxes & fees
31 Aug - 1 Sept
Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.

Landing Apartments near Virginia Union University

3.5 star property
8.6 out of 10, Excellent, (17)
"The neighborhood was quiet and it has nice food places around "
Landing Apartments near Virginia Union University

Amazing Private House Rental w/ pool! Richmond, VA

9.0 out of 10, Wonderful, (66)
"Enjoyed everything but couldn’t get in the pool.The people that came before us had a party. "
The price is AU$628
includes taxes & fees
23 Sept - 24 Sept
Amazing Private House Rental w/ pool! Richmond, VA

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

10.0 out of 10, Exceptional, (5)
"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 AU$314
includes taxes & fees
22 Sept - 23 Sept
Charming 1-bedroom suite with WiFi and AC in Bon Air

Walk to Museums & Breweries in Downtown Richmond

Walk to Museums & Breweries in Downtown Richmond

The Studio@ Eanes Drug

10.0 out of 10, Exceptional, (26)
"We had a great time staying at this studio with our dog. Very clean, any amenity you could want, and amazing location in a beautiful, historic neighborhood. We'd absolutely stay again!"
The price is AU$260
includes taxes & fees
27 Aug - 28 Aug
The Studio@ Eanes Drug

Lovely 2 Bedroom in the Heart of The Fan

9.4 out of 10, Exceptional, (66)
"Super easy and beautiful location. Very clean inside! The bed could be a little more comfortable, but other than that, no complaints!! 10/10 exactly the spot we needed to stroll around Richmond for a few days. "
The price is AU$485
includes taxes & fees
31 Aug - 1 Sept
Lovely 2 Bedroom in the Heart of The Fan

Tourist Homes of Richmond Church Hill North

4.0 star property
8.4 out of 10, Very good, (18)
"Amazing property! Will stay again!"
Tourist Homes of Richmond Church Hill North

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

9.8 out of 10, Exceptional, (122)
"This property had all the amenities, modern and clean decor, nice friendly neighborhood atmosphere, a little park a block away to walk the dog, and within walking distance to the many features of RVA. "
VCU • Fenced • Pet Friendly • Keyless • King Suite + 2 Queen Bedrooms

Historic Haven in Church Hill

10.0 out of 10, Exceptional, (26)
"Great apartment, very well appointed and close to lots of stuff."
The price is AU$269
includes taxes & fees
28 Aug - 29 Aug
Historic Haven in Church Hill

Midlothian 3 Bedroom getaway for up to 8 guests!

9.6 out of 10, Exceptional, (12)
"Great location. Everything was very clean and new. Very comfy beds and linens. Host was super accommodating as well. Will definitely go back "
The price is AU$842
includes taxes & fees
27 Aug - 28 Aug
Midlothian 3 Bedroom getaway for up to 8 guests!

Luxury Apt in Diamond District - Scott’s Addition

The price is AU$291
includes taxes & fees
8 Sept - 9 Sept
Luxury Apt in Diamond District - Scott’s Addition

The Grace Escape

10.0 out of 10, Exceptional, (25)
"We enjoyed our stay here. House was clean and it had everything we needed."
The Grace Escape

Vibrant 1-Bedroom Loft with Free Parking and Wifi

9.2 out of 10, Wonderful, (19)
"Clean and comfy. "
Vibrant 1-Bedroom Loft with Free Parking and Wifi

Studio Nest/2Queen beds/2TVs museums/free parking

10.0 out of 10, Exceptional, (44)
"My sister & I stayed here again after a wonderful experience last year. This place is a perfect location & comfortable accommodations. "
The price is AU$266
includes taxes & fees
22 Sept - 23 Sept
Studio Nest/2Queen beds/2TVs museums/free parking

~THE RETREAT~

9.8 out of 10, Exceptional, (22)
"This place is awesome so much room and activities. Mostly adults stayed but it would be great with smaller children as well. Very nice pool they would enjoy. Great neighborhood and peaceful. Definitely would stay again. Host was very responsive as well. Thank you!"
~THE RETREAT~

Downtown Living in Richmond's Amazing Shockoe Bottom

8.6 out of 10, Excellent, (28)
"There where used bandaids on the nightstand when I checked in which left a bad taste in my mouth :/"
The price is AU$382
includes taxes & fees
28 Aug - 29 Aug
Downtown Living in Richmond's Amazing Shockoe Bottom

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

10.0 out of 10, Exceptional, (215)
"We were in town for our daughter’s graduation from the University of Richmond. This property was minutes from the school and so convenient. Great kitchen, cozy house. Would stay again. "
Great Location. Close to about everywhere .Can't beat the value. Check reviews!

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

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

10.0 out of 10, Exceptional, (48)
"Fantastic place"
Cozy retreat just 1 mile from the Fine Creek Brewery & eclectic wedding venue.
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

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$260 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?

Charming 1-bedroom suite with WiFi and AC in Bon Air: This holiday home rental outside of Chesterfield offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities such as a fridge and a microwave can make your holiday run smoothly. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Chesterfield?

Expedia has 7 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. Castlewood 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.