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Chesterfield Holiday Rentals

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Our top choices for Chesterfield holiday rentals

1. 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, (6 reviews)
The price is NZ$422
includes taxes & fees
3 Sept - 4 Sept
Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.

2. Qualla Park

Qualla Park
Chesterfield County
10.0 out of 10, Exceptional, (4 reviews)
"The home was beautiful and amazing! Host was amazing too! Highly recommend!"
United Kingdom
Shannon W.
The price is NZ$733
includes taxes & fees
30 Aug - 31 Aug
Qualla Park

3. 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, (243 reviews)
"We had a great stay! Perfect get away for our anniversary. It had everything we needed and was super quiet with a great view. Thank you Captain Ron, for an amazing experience "
United States
Allison K.
The price is NZ$357
includes taxes & fees
3 Sept - 4 Sept
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city

4. 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, (121 reviews)
"Quaint, quiet, and cozy. Clean. Just what was wanted for a few quiet days. "
United States
norma W.
The price is NZ$357
includes taxes & fees
1 Sept - 2 Sept
A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations

5. MV GiaMaria

MV GiaMaria
3.5 star property
Richmond
9.2 out of 10, Wonderful, (16 reviews)
"So much fun!! Excellent host! Very informative. Loved the privacy and being on the water. The bed was super comfortable and the fireplace (electric) kept us warm and cozy. It was such a unique thing to do and we will be back!"
United States
Jane
The price is NZ$466
includes taxes & fees
2 Sept - 3 Sept
MV GiaMaria

6. Newly finished basement suite in Midlothian. Very clean and spacious.

Newly finished basement suite in Midlothian. Very clean and spacious.
Midlothian
10.0 out of 10, Exceptional, (5 reviews)
"Cute place. Very spacious and clean. Great communication. Would definitely stay again. Thank you!"
United States
Jeannie C.
The price is NZ$358
includes taxes & fees
20 Sept - 21 Sept
Newly finished basement suite in Midlothian. Very clean and spacious.

7. The Birdhouse - Cozy Cottage Retreat in Richmond

The Birdhouse - Cozy Cottage Retreat in Richmond
Swansboro West
10.0 out of 10, Exceptional, (6 reviews)
"The most beautifully finished cottage! Host very responsive!! Loved it."
United States
Stephanie S.
The price is NZ$339
includes taxes & fees
30 Aug - 31 Aug
The Birdhouse - Cozy Cottage Retreat in Richmond

8. Family friendly! Recline at Timberline..

Family friendly! Recline at Timberline..
South chesterfield
9.2 out of 10, Wonderful, (55 reviews)
"This is a beautiful home nice area We all enjoyed it I'm thinking to come back soon"
United States
golden c.
The price is NZ$535
includes taxes & fees
23 Sept - 24 Sept
Family friendly! Recline at Timberline..

9. Game Room + Yard: Updated House in Chester!

Game Room + Yard: Updated House in Chester!
3.0 star property
Chester
The price is NZ$706
includes taxes & fees
7 Sept - 8 Sept
Game Room + Yard: Updated House in Chester!

10. 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 NZ$503
includes taxes & fees
30 Aug - 31 Aug
Cookie B

11. Game Room + Yard: Updated House in Chester!

Game Room + Yard: Updated House in Chester!
Chester
9.4 out of 10, Exceptional, (3 reviews)
"Great stay. Super clean! Great communication with host. 30 mins from Richmond VA, great for exploring surrounding areas!"
United States
Akia S.
The price is NZ$723
includes taxes & fees
7 Sept - 8 Sept
Game Room + Yard: Updated House in Chester!

12. Private bedroom and bath!

Private bedroom and bath!
Midlothian
6.0 out of 10, (2 reviews)
"We had a lacrosse tournament at River city sports plex. This was perfect location to stay for us. Friendly and amazing combination with host. Extremely pleased with our stay"
United States
Ridge W.
The price is NZ$392
includes taxes & fees
3 Sept - 4 Sept
Private bedroom and bath!

13. 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, (94 reviews)
"Very clean, cozy and in an excellent location."
United States
Courtney W.
The price is NZ$307
includes taxes & fees
31 Aug - 1 Sept
The Studio@ Eanes Drug-Heart of the Historic District

14. Cozy 2-bedroom apartment in beautiful Fan District

Cozy 2-bedroom apartment in beautiful Fan District
Fan District
10.0 out of 10, Exceptional, (1 review)
"Check in was quick and easy. Our host communicated everything we needed to make the stay seamless. The apartment was very clean and had everything we needed to be comfortable. Location was perfect. Walkable to Careytown with fun shopping and plenty of places to eat. We so enjoyed the stay!"
United States
Dorothy A S.
The price is NZ$423
includes taxes & fees
31 Aug - 1 Sept
Cozy 2-bedroom apartment in beautiful Fan District

15. Historic Haven in Church Hill in The Heart of the Historic District

Historic Haven in Church Hill in The Heart of the Historic District
Church Hill
10.0 out of 10, Exceptional, (78 reviews)
"Nice stay"
United States
Danelle B.
The price is NZ$326
includes taxes & fees
30 Aug - 31 Aug
Historic Haven in Church Hill in The Heart of the Historic District

16. Luxe King Bd W Resort Amenities

Luxe King Bd W Resort Amenities
Moseley
9.4 out of 10, Exceptional, (11 reviews)
"Hotel options in this area are awful; this condo is a great alternative. Everything is basic but completely serviceable and completely met our needs. The location close to Brandermill nursing/assisted living is perfect."
United States
Lisa H.
The price is NZ$361
includes taxes & fees
13 Sept - 14 Sept
Luxe King Bd W Resort Amenities

17. Charming 3-bedroom townhome with WiFi in delightful Richmond

Charming 3-bedroom townhome with WiFi in delightful Richmond
Jahnke
10.0 out of 10, Exceptional, (7 reviews)
"Check-in was simple, good communication, property very much as described/depicted in the listing. Perfect location for our needs. "
United States
Mary C.
The price is NZ$711
includes taxes & fees
2 Sept - 3 Sept
Charming 3-bedroom townhome with WiFi in delightful Richmond

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

Charming 1-bedroom suite with WiFi and AC in Bon Air
Bon Air
9.8 out of 10, Exceptional, (9 reviews)
"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 "
United States
Jessica H.
The price is NZ$544
includes taxes & fees
30 Aug - 31 Aug
Charming 1-bedroom suite with WiFi and AC in Bon Air

19. Private Garden Home w/ Large Fenced Yard + Gazebo

Private Garden Home w/ Large Fenced Yard + Gazebo
Broad Rock
10.0 out of 10, Exceptional, (2 reviews)
"We had a great stay here for two nights! The beds were extremely comfortable and it was quiet and peaceful sleeping there both nights. We enjoyed the backyard very much - both our pets and kids. My son thought the gazebo with twinkle lights out back was so magical. :) We appreciate the cleanliness of the place and would only have appreciated a little space with maybe kids’ books, puzzles, or blocks or something. My young kiddos go crazy for those things when we stay at vacation rentals and it...
United States
Stacie C.
The price is NZ$578
includes taxes & fees
14 Sept - 15 Sept
Private Garden Home w/ Large Fenced Yard + Gazebo

20. 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
9.8 out of 10, Exceptional, (12 reviews)
"Amazing space. Great response time, our host was super friendly & helpful. The house was everything we were looking for and more, it was beautiful and the location was very convenient! "
United States
Michelle S.
The price is NZ$393
includes taxes & fees
2 Sept - 3 Sept
Private Guest house with Parking and Wi-Fi in a Central Location
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Chesterfield holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Chesterfield. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Chesterfield. Seeing all the best attractions is bound to make you fall in love with Chesterfield. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Chesterfield short-term rentals, that won’t be hard to do.

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?

Fantastic 5-bedroom Luxury home in charming Richmond: This holiday home rental outside of Chesterfield has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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?

Appomattox River and Swift Creek Reservoir are a couple of lovely local spots to get outside and enjoy nature. Pocahontas State Park and Chesterfield Historical Society of Virginia 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.