Chesterfield Holiday Rentals

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Our top choices for Chesterfield holiday rentals

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 AU$347
includes taxes & fees
22 Apr - 23 Apr
Stonewall Manor Cozy 1-bedroom with WiFi and AC on five star horse farm.

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 AU$601
includes taxes & fees
20 Apr - 21 Apr
3 BR Colonial Revival in 2 Acres, 5 min to State Park. Family & Pet Friendly!

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 AU$303
includes taxes & fees
20 Apr - 21 Apr
A Cozy And Classic Hatteras 43' Yacht In One Of The Best James River Locations

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 AU$303
includes taxes & fees
20 Apr - 21 Apr
A Warm and Cozy 50' Houseboat in gated, quaint and peaceful marina near the city

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 AU$417
includes taxes & fees
20 Apr - 21 Apr
Cookie B

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 AU$226
includes taxes & fees
20 Apr - 21 Apr
The Farmhouse Retreat

The Studio@ Eanes Drug

The Studio@ Eanes Drug
Church Hill
10.0 out of 10, Exceptional, (67 reviews)
"Room was wonderful, very clean & cozy. Great location!"
United States
Kirk
The price is AU$266
includes taxes & fees
20 Apr - 21 Apr
The Studio@ Eanes Drug

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 AU$165
includes taxes & fees
25 Apr - 26 Apr
Magnolias, a chill out place.

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

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 AU$205
includes taxes & fees
20 Apr - 21 Apr
Carytown cozy nest private room Fenced Yard

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 AU$275
includes taxes & fees
21 Apr - 22 Apr
Carytown nest/King Bed/fully fenced

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 AU$351
includes taxes & fees
21 Apr - 22 Apr
Private Guest house with Parking and Wi-Fi in a Central Location

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 AU$223
includes taxes & fees
20 Apr - 21 Apr
Urban Bloom/King Bed/2TVs/Free Parking/Museums

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, (78 reviews)
"Cozy, chic, immaculate apartment, centrally located. "
United States
Deborah
The price is AU$258
includes taxes & fees
20 Apr - 21 Apr
Heart of the Arts District Penthouse - West Broad VCU MCV Prime Downtown!

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 AU$379
includes taxes & fees
11 May - 12 May
Oaks Retreat Carytown House: Family & Pet Friendly

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 AU$329
includes taxes & fees
20 Apr - 21 Apr
Carytown Gem: Family-Friendly Apartment with Yard

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 AU$275
includes taxes & fees
26 Apr - 27 Apr
Historic Haven in Church Hill

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 AU$458
includes taxes & fees
20 Apr - 21 Apr
Downtown Living in Richmond's Amazing Shockoe Bottom

The SageBrush Cottage

The SageBrush Cottage
North Highland Park
The price is AU$449
includes taxes & fees
22 Apr - 23 Apr
The SageBrush Cottage

Cozy Nest Near The River

Cozy Nest Near The River
Woodland Heights
10.0 out of 10, Exceptional, (2 reviews)
"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 AU$246
includes taxes & fees
20 Apr - 21 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

Find out more about Chesterfield

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$258 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 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.