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Chesterfield Vacation Rentals

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  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Chesterfield vacation rentals

Property grounds

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 location is beautiful! Kristina was very prompt in answering my questions and very accommodating. Wonderful stay."
United States
Connie D.
$223 nightly
The price is $256
Sep 1 - Sep 2
Total with taxes and fees
Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.
Coffee/tea maker, fridge, microwave, oven

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.
$434 nightly
The price is $442
Sep 1 - Sep 2
Total with taxes and fees
Qualla Park
Marina

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.
$189 nightly
The price is $216
Sep 3 - Sep 4
Total with taxes and fees
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
Lobby

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)
"What an amazing and unique experience. We had great weather, which allowed us a lot of time outside on the boat. The bed is very comfortable and the furnishings are super cute. Ron is incredibly generous and communicative, would definitely recommend!"
United States
Lindsay D.
$188 nightly
The price is $215
Sep 1 - Sep 2
Total with taxes and fees
A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations
View from property

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
$243 nightly
The price is $277
Sep 1 - Sep 2
Total with taxes and fees
MV GiaMaria
Terrace/patio

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.
$188 nightly
The price is $216
Sep 20 - Sep 21
Total with taxes and fees
Newly finished basement suite in Midlothian. Very clean and spacious.
Smart TV, fireplace

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.
$203 nightly
The price is $206
Sep 2 - Sep 3
Total with taxes and fees
The Birdhouse - Cozy Cottage Retreat in Richmond
3 bedrooms, desk, iron/ironing board, WiFi (free)

8. Family friendly! Recline at Timberline..

Family friendly! Recline at Timberline..
South chesterfield
9.4 out of 10, Exceptional, (56 reviews)
"This is a beautiful home nice area We all enjoyed it I'm thinking to come back soon"
United States
golden c.
$282 nightly
The price is $325
Sep 23 - Sep 24
Total with taxes and fees
Family friendly! Recline at Timberline..
House (3 Bedrooms) | Interior

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

Game Room + Yard: Updated House in Chester!
3.0 star property
Chester
$360 nightly
The price is $410
Sep 7 - Sep 8
Total with taxes and fees
Game Room + Yard: Updated House in Chester!
Front of property

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
$263 nightly
The price is $299
Sep 1 - Sep 2
Total with taxes and fees
Cookie B
TV, fireplace, foosball, books

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.
$369 nightly
The price is $425
Sep 7 - Sep 8
Total with taxes and fees
Game Room + Yard: Updated House in Chester!
Exterior

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.
$206 nightly
The price is $237
Sep 1 - Sep 2
Total with taxes and fees
Private bedroom and bath!
Coffee/tea maker, fridge, microwave, oven

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.
$166 nightly
The price is $190
Sep 2 - Sep 3
Total with taxes and fees
The Studio@ Eanes Drug-Heart of the Historic District
Dining

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.
$222 nightly
The price is $254
Sep 1 - Sep 2
Total with taxes and fees
Cozy 2-bedroom apartment in beautiful Fan District
Coffee/tea maker, fridge, microwave, oven

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.
$171 nightly
The price is $195
Sep 1 - Sep 2
Total with taxes and fees
Historic Haven in Church Hill in The Heart of the Historic District
Fridge, microwave, oven, stovetop

16. Luxe King Bd W Resort Amenities

Luxe King Bd W Resort Amenities
Moseley
9.4 out of 10, Exceptional, (11 reviews)
"Could use a comfier couch facing the TV other than that nice spot"
United States
Keith D.
$179 nightly
The price is $206
Sep 13 - Sep 14
Total with taxes and fees
Luxe King Bd W Resort Amenities
Smart TV

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.
$406 nightly
The price is $464
Sep 1 - Sep 2
Total with taxes and fees
Charming 3-bedroom townhome with WiFi in delightful Richmond
Smart TV, fireplace, computer monitors

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
9.0 out of 10, Wonderful, (10 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.
$282 nightly
The price is $325
Sep 1 - Sep 2
Total with taxes and fees
Charming 1-bedroom suite with WiFi and AC in Bon Air
Terrace/patio

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.
$310 nightly
The price is $355
Sep 15 - Sep 16
Total with taxes and fees
Private Garden Home w/ Large Fenced Yard + Gazebo
1 bedroom, desk, iron/ironing board, WiFi

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.
$213 nightly
The price is $244
Sep 2 - Sep 3
Total with taxes and fees
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

Comfort Suites At Virginia Center Commons

Comfort Suites At Virginia Center Commons

10/10 Excellent
"I love how peaceful and quiet it was and it wasn't a hassle at all"
Christian 3-night trip
Posted 4 hours ago
Comfort Suites At Virginia Center Commons

Find out more about Chesterfield

Everything you need to know about Chesterfield vacation rentals

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

Chesterfield vacation 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 low season months. For more hustle and bustle, you may prefer to visit Chesterfield in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $190 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chesterfield rentals

At Expedia, we put the best Chesterfield vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Chesterfield?

Yes, we give you a choice of vacation rentals close to popular local attractions in Chesterfield, or you can choose a more secluded option if you're looking for relaxation. 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 vacation rentals that Chesterfield has to offer?

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

How many vacation rentals are there in Chesterfield?

Expedia has 6 vacation 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 vacation rentals like in Chesterfield?

Vacation rentals are privately owned properties you can stay in for a short or long stay in Chesterfield. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for a small group gathering.