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Chesterfield Holiday Rentals

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Holiday Rentals in Chesterfield

A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
9.6 out of 10, Exceptional, (194)
"Best spot we could have chosen. On the river but not a lot of traffic. The fishing was great. The kid and our dogs had an absolute blast. Captain Ron was great! We cant wait to go back"
The price is AU$294
includes taxes & fees
4 July - 5 July
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
Cozy Get-A-Way in Neighborhood On 3 Lakes, With Fishing Docks, Firepit, Kayaks
9.8 out of 10, Exceptional, (10)
"We thoroughly enjoyed staying in your cute house."
The price is AU$629
includes taxes & fees
23 June - 24 June
Cozy Get-A-Way in Neighborhood On 3 Lakes, With Fishing Docks, Firepit, Kayaks
Downtown Living in Richmond's Amazing Shockoe Bottom
9.8 out of 10, Exceptional, (13)
"Exactly as described and in a nice and convenient location"
The price is AU$392
includes taxes & fees
3 July - 4 July
Downtown Living in Richmond's Amazing Shockoe Bottom
Garden Penthouse in RVA! 3 Bedroom, 3 Bath!
10.0 out of 10, Exceptional, (10)
"This is the place for you and yours! We came to Richmond to see the sites and tour civil war era places. It was always so nice to come "home""
Garden Penthouse in RVA! 3 Bedroom, 3 Bath!
Newly Renovated Historic Home < 2 Mi to Downtown!
9.8 out of 10, Exceptional, (47)
"Enjoyed our time"
Newly Renovated Historic Home < 2 Mi to Downtown!
G6 Central location STUDIO museums FREE PARKING
10.0 out of 10, Exceptional, (19)
"We had a great time staying here. My sister and I ran the Monument 10K and it was an ideal location, just a short walk to the start line. We would absolutely stay here again!"
The price is AU$225
includes taxes & fees
3 July - 4 July
G6 Central location STUDIO museums FREE PARKING
Central location w/ large fenced yard FIRE-PIT
10.0 out of 10, Exceptional, (23)
"A nice stay for a family with a dog. Also, the host was very helpful when I needed to change a detail of my reservation."
The price is AU$495
includes taxes & fees
23 June - 24 June
Central location w/ large fenced yard FIRE-PIT
The Bamboo House! Dog-Friendly Home n RVA Sleeps 8
9.8 out of 10, Exceptional, (9)
"Good location. Ample sleeping space. No issues."
The Bamboo House! Dog-Friendly Home n RVA Sleeps 8
Cozy Cape Cod Home!
10.0 out of 10, Exceptional, (26)
"Great place, convenient, and wonderful back yard!"
Cozy Cape Cod Home!
Magnolias, a chill out place.
10.0 out of 10, Exceptional, (8)
"Great place very clean Host was great Definitely would rent again thank you"
The price is AU$190
includes taxes & fees
27 June - 28 June
Magnolias, a chill out place.
The lake house at lake chesdin
10.0 out of 10, Exceptional, (8)
"Our first time staying at this property. So glad we found it - it will be our first choice for future trips to Chesdin. The house is spacious and wonderfully appointed. Kitchen has everything you'll need. Plenty of parking (we had 2 boats/trucks). The neighborhood is quiet and safe. House sits right on the water w/ a fabulous view of the sunset. This place is great for a family get-away or homebase for a fishing trip. Minutes to the Whippernock ramp."
The price is AU$636
includes taxes & fees
8 July - 9 July
The lake house at lake chesdin
Downtown Living in Historic Richmond Loft
8.4 out of 10, Very good, (42)
"The flat was centrally located. It was a unique two story build out in an old building. We were greeted at the foyer by a Colo-guard box but it wasn’t really in the way as we dragged our luggage down the. Crazy long hallway in the first floor to our room. The two bedrooms are in second floor and each have a bathroom, one is en-suite. This one has to windows to outside which makes it a bit dark. The second bedroom was nice and had a small window through which I could hear loud thumping music for...
The price is AU$486
includes taxes & fees
27 June - 28 June
Downtown Living in Historic Richmond Loft
Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!
10.0 out of 10, Exceptional, (44)
"The stay was great overall. The property is a beautiful restoration. The apartment was as advertised . The comfort level left a bit to be desired . But the absolute best part was the communication with the owner and staff. Also your cleaning services clearly don’t vacuum"
Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!
Lovely 1-Bedroom Loft with Free Parking and Wifi
8.8 out of 10, Excellent, (10)
"We were in town for a tournament at the convention center and looking for something walking distance. This was perfect! Less than 5 min walk. The loft had everything we could have asked for and was immaculate. Instructions for entering the loft were clear and easy to follow, as well as communication before, during and after was A+! My only suggestion is that the outside of the place was difficult to find - possibly a photo of the entrance would help! But once we found it, the rest of the stay...
The price is AU$394
includes taxes & fees
27 June - 28 June
Lovely 1-Bedroom Loft with Free Parking and Wifi
Industrial Chic Loft in the Heart of Downtown Richmond!
8.8 out of 10, Excellent, (8)
"I loved it was so close to everything history this place was amazing and will be back in the future "
Industrial Chic Loft in the Heart of Downtown Richmond!
The Happy Place, Kingsize bed.
9.6 out of 10, Exceptional, (4)
"The listing was as depicted. The owner was very responsive and answered all our questions. She even brought us a new coffee pot!"
The Happy Place, Kingsize bed.
The Bike Path House! Cozy 2 BR w/ Fireplace
9.0 out of 10, Wonderful, (10)
"We loved the central location & proximity to the Bike Path. Very clean & cozy."
The Bike Path House! Cozy 2 BR w/ Fireplace
Richmond Home w/ Fire Pit - 12 Mi to Downtown
10.0 out of 10, Exceptional, (9)
"Convenient to Broad St.and Parham St. in Richmond. Easy access to everything."
Richmond Home w/ Fire Pit - 12 Mi to Downtown
Terre Haute Manor Farmhouse w/ Gardens & Deck!
10.0 out of 10, Exceptional, (19)
"I took two teams (UMASS & JMU) to the college super regional Pickleball tournament. The house was fantastic because it was affordable for college kids (though one needed to be 30 years of age to book it…I exceed that age), it had lots of beds and enough bathrooms and a kitchen. I recommend getting there in the daylight hours because it is a little off the beaten path and dark when you arrive but it was perfect fit for our needs - great hospitality! Beautiful animals in the property too (donkeys...
Terre Haute Manor Farmhouse w/ Gardens & Deck!
Great Location. Close to about everywhere .Can't beat the value. Check reviews!
10.0 out of 10, Exceptional, (172)
"The house was as depicted in a quiet and pleasant neighborhood. We had everything we needed. It was nice and clean."
Great Location. Close to about everywhere .Can't beat the value. Check reviews!
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See all available properties in Chesterfield
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.

Chesterfield Holiday Home Travel Info

Other types of properties in Chesterfield you may be interested in

Drury Plaza Hotel Richmond
3.0 star property
9.6 out of 10, Exceptional, (2318)
"The room was cozy. The accommodations were plentiful. Great stay! Would stay again in a heartbeat "
The price is AU$200
includes taxes & fees
3 July - 4 July
Drury Plaza Hotel Richmond
Graduate Richmond
4.0 star property
8.4 out of 10, Very good, (1155)
"Great stay, staff was there when needed and hotel was clean. Really cool deco and lighting at night .. if you pay attention to the tiny details like myself. Wish I had gone up to rooftop at night, but was a long day and I fell asleep easily. Will be back again and again .. until things change. Let’s hope they stay the same or better! Thanks Graduate "
The price is AU$264
includes taxes & fees
3 July - 4 July
Graduate Richmond
Best Western Premier Richmond City Gateway
3.0 star property
7.8 out of 10, Good, (929)
"Easy on and off 95"
The price is AU$183
includes taxes & fees
30 June - 1 July
Best Western Premier Richmond City Gateway
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.

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$190 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?

Cozy Get-A-Way in Neighborhood On 3 Lakes, With Fishing Docks, Firepit, Kayaks: This holiday home rental outside of Chesterfield offers a fireplace, 1 hot tub and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Chesterfield?

Expedia has 9 holiday rentals for your stay in Chesterfield.

What can I see and do in Chesterfield?

Pocahontas State Park and Appomattox River are a couple of lovely local spots to get outside and enjoy nature. Castlewood and Pocahontas State Park Museum 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.

Recent reviews of Chesterfield properties
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