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Chesterfield Vacation Rentals

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Vacation Rentals in Chesterfield

A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
Property grounds
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
9.6 out of 10, Exceptional, 194 reviews
"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 $100
$194 total
includes taxes & fees
Jun 24 - Jun 25
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
Property grounds
Cozy Get-A-Way in Neighborhood On 3 Lakes, With Fishing Docks, Firepit, Kayaks
9.8 out of 10, Exceptional, 10 reviews
"We thoroughly enjoyed staying in your cute house."
The price is $199
$414 total
includes taxes & fees
Jun 20 - Jun 21
Cozy Get-A-Way in Neighborhood On 3 Lakes, With Fishing Docks, Firepit, Kayaks
Downtown Living in Richmond's Amazing Shockoe Bottom
Fridge, microwave, oven, stovetop
Downtown Living in Richmond's Amazing Shockoe Bottom
9.8 out of 10, Exceptional, 13 reviews
"Exactly as described and in a nice and convenient location"
The price is $121
$258 total
includes taxes & fees
Jul 1 - Jul 2
Downtown Living in Richmond's Amazing Shockoe Bottom
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Garden Penthouse in RVA! 3 Bedroom, 3 Bath!
Fridge, microwave, oven, stovetop
Garden Penthouse in RVA! 3 Bedroom, 3 Bath!
10.0 out of 10, Exceptional, 9 reviews
"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!
Fridge, microwave, stovetop, dishwasher
Newly Renovated Historic Home < 2 Mi to Downtown!
9.8 out of 10, Exceptional, 47 reviews
"Enjoyed our time"
Newly Renovated Historic Home < 2 Mi to Downtown!
G6 Central location STUDIO museums FREE PARKING
TV, offices
G6 Central location STUDIO museums FREE PARKING
10.0 out of 10, Exceptional, 19 reviews
"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 $68
$151 total
includes taxes & fees
Jul 3 - Jul 4
G6 Central location STUDIO museums FREE PARKING
Central location w/ large fenced yard FIRE-PIT
Terrace/patio
Central location w/ large fenced yard FIRE-PIT
10.0 out of 10, Exceptional, 23 reviews
"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 $165
$344 total
includes taxes & fees
Jun 24 - Jun 25
Central location w/ large fenced yard FIRE-PIT
The Bamboo House! Dog-Friendly Home n RVA Sleeps 8
Fridge, microwave, oven, stovetop
The Bamboo House! Dog-Friendly Home n RVA Sleeps 8
9.8 out of 10, Exceptional, 8 reviews
"Good location. Ample sleeping space. No issues."
The Bamboo House! Dog-Friendly Home n RVA Sleeps 8
Cozy Cape Cod Home!
Smart TV
Cozy Cape Cod Home!
10.0 out of 10, Exceptional, 26 reviews
"Great place, convenient, and wonderful back yard!"
Cozy Cape Cod Home!
Magnolias, a chill out place.
Exterior
Magnolias, a chill out place.
10.0 out of 10, Exceptional, 8 reviews
"Magnolias is exactly what it is advertising. A great place to stay for a few nights when visiting RVA. Super close to the RIC. Easy to get to and from downtown. Very comfortable. Well worth the price."
The price is $69
$124 total
includes taxes & fees
Jun 24 - Jun 25
Magnolias, a chill out place.
The lake house at lake chesdin
Smart TV, fireplace
The lake house at lake chesdin
10.0 out of 10, Exceptional, 6 reviews
"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 $299
$418 total
includes taxes & fees
Jul 8 - Jul 9
The lake house at lake chesdin
Downtown Living in Historic Richmond Loft
Fridge, microwave, oven, stovetop
Downtown Living in Historic Richmond Loft
8.4 out of 10, Very Good, 42 reviews
"Wonderful apartment, plenty of room for us and located near many things to do!"
The price is $156
$320 total
includes taxes & fees
Jun 20 - Jun 21
Downtown Living in Historic Richmond Loft
Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!
Interior
Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!
10.0 out of 10, Exceptional, 44 reviews
"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
Fridge, microwave, oven, stovetop
Lovely 1-Bedroom Loft with Free Parking and Wifi
8.8 out of 10, Excellent, 10 reviews
"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 $121
$259 total
includes taxes & fees
Jun 20 - Jun 21
Lovely 1-Bedroom Loft with Free Parking and Wifi
Industrial Chic Loft in the Heart of Downtown Richmond!
Exterior
Industrial Chic Loft in the Heart of Downtown Richmond!
8.8 out of 10, Excellent, 8 reviews
"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.
Fridge, microwave, oven, stovetop
The Happy Place, Kingsize bed.
9.6 out of 10, Exceptional, 4 reviews
"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
Property grounds
The Bike Path House! Cozy 2 BR w/ Fireplace
9.0 out of 10, Wonderful, 10 reviews
"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
Fridge, microwave, stovetop, dishwasher
Richmond Home w/ Fire Pit - 12 Mi to Downtown
10.0 out of 10, Exceptional, 9 reviews
"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!
Fridge, microwave, stovetop, dishwasher
Terre Haute Manor Farmhouse w/ Gardens & Deck!
10.0 out of 10, Exceptional, 19 reviews
"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!
Property grounds
Great Location. Close to about everywhere .Can't beat the value. Check reviews!
10.0 out of 10, Exceptional, 172 reviews
"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!
Don't see what you're looking for?
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 Vacation Rental Travel Info

Popular accommodation
Chesterfield private vacation homes
Known landmarks
Pocahontas State Park, Uptown Alley and Pocahontas State Park Museum
International airport
Richmond, VA (RIC-Richmond Intl.)

Other types of properties in Chesterfield you may be interested in

Drury Plaza Hotel Richmond
Lobby
Drury Plaza Hotel Richmond
3.0 star property
9.6 out of 10, Exceptional, 2,358 reviews
"The room was cozy. The accommodations were plentiful. Great stay! Would stay again in a heartbeat "
The price is $126
$147 total
includes taxes & fees
Jun 24 - Jun 25
Drury Plaza Hotel Richmond
Graduate Richmond
Rooftop terrace
Graduate Richmond
4.0 star property
8.4 out of 10, Very Good, 1,152 reviews
"The only thing I think needs a upgrade is the pool area small and wasn’t the best..I I may have also been the time of the year we went too Wasn’t hot enough yet for the pool "
The price is $151
$176 total
includes taxes & fees
Jul 1 - Jul 2
Graduate Richmond
Best Western Premier Richmond City Gateway
Lobby
Best Western Premier Richmond City Gateway
3.0 star property
7.8 out of 10, Good, 926 reviews
"Easy on and off 95"
The price is $104
$121 total
includes taxes & fees
Jun 26 - Jun 27
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 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 $68 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.

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?

Cozy Get-A-Way in Neighborhood On 3 Lakes, With Fishing Docks, Firepit, Kayaks: This vacation home rental outside of Chesterfield offers a fireplace, a spa tub, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Chesterfield?

Expedia has 9 vacation 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 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.

Recent reviews of Chesterfield properties
Expedia verified reviews

Hampton Inn Richmond West Innsbrook

Hampton Inn Richmond West Innsbrook

5/5 Excellent
"Excellent stay at this hotel. Facilities are excellent and service was very good. The hotel is located in a very nice area with several dining options within walking distance. Will definitely stay there again when in the area."
A verified traveler stayed at Hampton Inn Richmond West Innsbrook
Posted 9 hours ago
Hampton Inn Richmond West Innsbrook