Chesterfield Holiday Rentals

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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Chesterfield holiday rentals

Property grounds

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, (5 reviews)
"Visiting friends "
United States
Todd K.
The price is HK$705
HK$1,893 total
includes taxes & fees
22 Apr - 23 Apr
Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.
3 bedrooms, desk, iron/ironing board, free WiFi

3 BR Colonial Revival in 2 Acres, 5 min to State Park. Family & Pet Friendly!

3 BR Colonial Revival in 2 Acres, 5 min to State Park. Family & Pet Friendly!
Chesterfield County
10.0 out of 10, Exceptional, (2 reviews)
"Easy check in. House is wonderful. These hosts have thought of everything!!"
United States
Diane L.
The price is HK$1,410
HK$3,419 total
includes taxes & fees
19 Apr - 20 Apr
3 BR Colonial Revival in 2 Acres, 5 min to State Park. Family & Pet Friendly!
Lobby

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, (116 reviews)
"2nd time staying at this property and definitely won’t be the last! Amazing location and great host."
United States
Alexis S.
The price is HK$901
HK$1,656 total
includes taxes & fees
22 Apr - 23 Apr
A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations
Marina

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, (230 reviews)
"Truly unique, perfectly appointed, cozy and warm with stunning views. A very special experience."
United States
Kristin K.
The price is HK$901
HK$1,656 total
includes taxes & fees
22 Apr - 23 Apr
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city
Front of property

Cookie B

Cookie B
3.0 star property
Richmond
9.6 out of 10, Exceptional, (8 reviews)
"Capt. Ron has a charming, welcoming, and delightful alternative to a standard hotel room on offer here. Super fun!"
United States
Robert
The price is HK$1,714
HK$2,345 total
includes taxes & fees
22 Apr - 23 Apr
Cookie B
1 bedroom, WiFi

The Farmhouse Retreat

The Farmhouse Retreat
Mechanicsville
10.0 out of 10, Exceptional, (4 reviews)
"Had a great stay while fishing the james river. "
United States
Travis D.
The price is HK$697
HK$1,253 total
includes taxes & fees
26 Apr - 27 Apr
The Farmhouse Retreat
Fridge, microwave, oven, stovetop

The Studio@ Eanes Drug

The Studio@ Eanes Drug
Church Hill
10.0 out of 10, Exceptional, (65 reviews)
"Room was wonderful, very clean & cozy. Great location!"
United States
Kirk
The price is HK$1,136
HK$1,477 total
includes taxes & fees
27 Apr - 28 Apr
The Studio@ Eanes Drug
1 bedroom, in-room safe, free WiFi, bed sheets

Magnolias, a chill out place.

Magnolias, a chill out place.
Richmond
9.2 out of 10, Wonderful, (22 reviews)
"Enjoyed my stay a lot! The property definitely has charm, the experience was very laid back. "
United States
Grace
The price is HK$486
HK$914 total
includes taxes & fees
24 Apr - 25 Apr
Magnolias, a chill out place.
Terrace/patio

Backyard Fire-Pit, Modern, Roomy, 7 Min Downtown

Backyard Fire-Pit, Modern, Roomy, 7 Min Downtown
Northern Barton Heights
9.6 out of 10, Exceptional, (16 reviews)
"I loved it 100% recommend "
United States
Milton O.
The price is HK$940
HK$3,286 total
includes taxes & fees
17 May - 18 May
Backyard Fire-Pit, Modern, Roomy, 7 Min Downtown
Dining

Carytown cozy nest private room Fenced Yard

Carytown cozy nest private room Fenced Yard
Carytown
9.8 out of 10, Exceptional, (28 reviews)
"Everything was smooth and as promised. We recommend this spot!"
United States
Stefin P.
The price is HK$588
HK$1,135 total
includes taxes & fees
12 May - 13 May
Carytown cozy nest private room Fenced Yard
Interior

Carytown nest/King Bed/fully fenced

Carytown nest/King Bed/fully fenced
Carytown
9.6 out of 10, Exceptional, (41 reviews)
"Loved it! Perfect size for the three of us and great amenities. Outside was very icy though."
United States
Kevin
The price is HK$760
HK$1,523 total
includes taxes & fees
3 May - 4 May
Carytown nest/King Bed/fully fenced
1 bedroom, desk, iron/ironing board, WiFi

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
10.0 out of 10, Exceptional, (6 reviews)
"A perfect VRBO: clean, tastefully decorated, great location, safe, comfortable bed, great communication, and an overall warm welcoming feel. I would love to stay in Amanda’s VRBO again when visiting Richmond."
United States
Sandra D.
The price is HK$598
HK$1,847 total
includes taxes & fees
21 Apr - 22 Apr
Private Guest house with Parking and Wi-Fi in a Central Location
Terrace/patio

Urban Bloom/King Bed/2TVs/Free Parking/Museums

Urban Bloom/King Bed/2TVs/Free Parking/Museums
Fan District
9.8 out of 10, Exceptional, (56 reviews)
"Nice location. "
United States
Michael S.
The price is HK$666
HK$1,304 total
includes taxes & fees
20 Apr - 21 Apr
Urban Bloom/King Bed/2TVs/Free Parking/Museums
Dining

Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!

Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!
Downtown Richmond
9.8 out of 10, Exceptional, (77 reviews)
"Cozy, chic, immaculate apartment, centrally located. "
United States
Deborah
The price is HK$719
HK$1,538 total
includes taxes & fees
22 Apr - 23 Apr
Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!
TV, books, offices

Oaks Retreat Carytown House: Family & Pet Friendly

Oaks Retreat Carytown House: Family & Pet Friendly
Randolph
9.2 out of 10, Wonderful, (15 reviews)
"Clean, comfortable, parking available, great communication with host. "
United States
Glori B.
The price is HK$987
HK$2,180 total
includes taxes & fees
11 May - 12 May
Oaks Retreat Carytown House: Family & Pet Friendly
Interior

Carytown Gem: Family-Friendly Apartment with Yard

Carytown Gem: Family-Friendly Apartment with Yard
Carytown
9.8 out of 10, Exceptional, (74 reviews)
"Location was great. Very walkable town"
United States
patricia h.
The price is HK$885
HK$1,793 total
includes taxes & fees
20 Apr - 21 Apr
Carytown Gem: Family-Friendly Apartment with Yard
Fridge, microwave, oven, stovetop

Historic Haven in Church Hill

Historic Haven in Church Hill
Church Hill
10.0 out of 10, Exceptional, (62 reviews)
"Excellent accommodations!Great walkable location near local cafes & restaurants with a friendly neighborhood vibe."
United States
Patricia N.
The price is HK$1,175
HK$1,522 total
includes taxes & fees
29 Apr - 30 Apr
Historic Haven in Church Hill
Interior

Downtown Living in Richmond's Amazing Shockoe Bottom

Downtown Living in Richmond's Amazing Shockoe Bottom
Downtown Richmond
8.6 out of 10, Excellent, (33 reviews)
"Was I great place to stay! Very responsive and gave all the info you need to make the trip and stay easy! "
United States
Dillon D.
The price is HK$897
HK$2,546 total
includes taxes & fees
22 Apr - 23 Apr
Downtown Living in Richmond's Amazing Shockoe Bottom
Living area

The SageBrush Cottage

The SageBrush Cottage
North Highland Park
The price is HK$987
HK$2,516 total
includes taxes & fees
20 Apr - 21 Apr
The SageBrush Cottage
Interior

Cozy Nest Near The River

Cozy Nest Near The River
Woodland Heights
10.0 out of 10, Exceptional, (1 review)
"Very nice apartment, seemed like it was brand new. Very clean, convenient location and host responds quickly to messages"
United States
Ken S.
The price is HK$1,011
HK$1,364 total
includes taxes & fees
22 Apr - 23 Apr
Cozy Nest Near The River
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

8/10 Good
"This is a nice area surrounded by restaurants. The room was clean. The hot tub was dirty around the edges but they had cleaned it by our second night. Breakfast was basic eggs, sausage, biscuits. The front concrete was dirty in front of the hotel. Staff was nice. "
Adlois 2-night trip
Posted 7 hours ago
Comfort Suites At Virginia Center Commons

Find out more about Chesterfield

Search for holiday rentals in Chesterfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesterfield using one of the methods below:

  • View our selection of featured holiday rentals in Chesterfield
  • Use the map to find apartments and other holiday homes in the Chesterfield neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chesterfield while they last

Look no further and take a look at our great range of rental properties in Chesterfield!

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 walkable downtown retreat, 3 minutes to VCU: This holiday home rental outside of Chesterfield is located in the city centre, and offers a selection of games, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 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 8 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. Pocahontas State Park and Magnolia Grange 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.