Book Holiday Homes in Chesterfield

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Featured Holiday Homes in Chesterfield

The Grace Escape

The Grace Escape

Richmond VA
Stay at this holiday home in Richmond. Enjoy a garden, laundry facilities and patios. Popular attractions Richmond Raceway and Broad Street are located ...
Opens in a new windowThe Grace Escape
In the Village Of Powhatan- walking distance to owners restaurant

In the Village Of Powhatan- walking distance to owners restaurant

Powhatan VA
Stay at this holiday home in Powhatan. Enjoy free Wi-Fi, laundry facilities and patios. Popular attraction Mill Quarter Plantation Golf Club is located ...
Opens in a new windowIn the Village Of Powhatan- walking distance to owners restaurant
Super Location. Close to about everywhere .Great value.Over 200 reviews!!

Super Location. Close to about everywhere .Great value.Over 200 reviews!!

Richmond VA
Stay at this holiday home in Richmond. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Richmond Raceway and Broad Street are located ...
Opens in a new windowSuper Location. Close to about everywhere .Great value.Over 200 reviews!!
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Backyard Fire-Pit, Modern, Roomy, 7 Min Downtown

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

Richmond VA
Stay at this holiday home in Richmond. Enjoy laundry facilities, patios and air conditioning. Popular attractions Broad Street and Black History Museum are located ...
Opens in a new windowBackyard Fire-Pit, Modern, Roomy, 7 Min Downtown
Cozy walkable downtown retreat, 3 minutes to VCU

Cozy walkable downtown retreat, 3 minutes to VCU

Richmond VA
The price is NZ$800 per night from 4 May to 5 May
NZ$800
4 May - 5 May
includes taxes & fees
Stay at this holiday home in Richmond. Enjoy free Wi-Fi, laundry facilities and an in-room coffee maker. Popular attractions Broad Street and Black History Museum ...
Opens in a new windowCozy walkable downtown retreat, 3 minutes to VCU
Cozy retreat just 1 mile from the Fine Creek Brewery & eclectic wedding venue.

Cozy retreat just 1 mile from the Fine Creek Brewery & eclectic wedding venue.

Powhatan VA
Stay at this holiday home in Powhatan. Enjoy free Wi-Fi, laundry facilities and patios.
Opens in a new windowCozy retreat just 1 mile from the Fine Creek Brewery & eclectic wedding venue.
Stylish 4BR/2.5BA home for up to 10 guests with kitchen, patio, and workspace.

Stylish 4BR/2.5BA home for up to 10 guests with kitchen, patio, and workspace.

Glen Allen VA
Stay at this holiday home in Glen Allen. Enjoy free Wi-Fi, laundry facilities and balconies. Popular attractions The Crossings Golf Club and Lewis Ginter Botanical ...
Opens in a new windowStylish 4BR/2.5BA home for up to 10 guests with kitchen, patio, and workspace.
Richmond Family Retreat: 3BR House, fully fenced, Parking

Richmond Family Retreat: 3BR House, fully fenced, Parking

Richmond VA
The price is NZ$712 per night from 4 May to 5 May
NZ$712
4 May - 5 May
includes taxes & fees
Stay at this holiday home in Richmond. Enjoy a garden, laundry facilities and an in-room coffee maker. Popular attractions Broad Street and Shops at Willow Lawn ...
Opens in a new windowRichmond Family Retreat: 3BR House, fully fenced, Parking
Stylish retreat in charming Richmond with Private Sauna and other modern touches

Stylish retreat in charming Richmond with Private Sauna and other modern touches

Richmond VA
Stay at this holiday home in Richmond. Enjoy laundry facilities, an in-room coffee maker and in-room fireplaces. Popular attractions Broad Street and Belle Isle ...
Opens in a new windowStylish retreat in charming Richmond with Private Sauna and other modern touches
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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 Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Chesterfield vacation homes are the perfect way for you to wing it.

Holiday houses in Chesterfield let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Chesterfield in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Chesterfield adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Chesterfield with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Chesterfield vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Chesterfield Holiday Homes essential information

Accommodation
287 Holiday Homes
Lowest Price
NZ$259
Highest Price
NZ$800
Popular accommodation
The Grace Escape, In the Village Of Powhatan- walking distance to owners restaurant, Super Location. Close to about everywhere .Great value.Over 200 reviews!!, Backyard Fire-Pit, Modern, Roomy, 7 Min Downtown, Cozy walkable downtown retreat, 3 minutes to VCU, Cozy retreat just 1 mile from the Fine Creek Brewery & eclectic wedding venue. , Stylish 4BR/2.5BA home for up to 10 guests with kitchen, patio, and workspace., Richmond Family Retreat: 3BR House, fully fenced, Parking, Stylish retreat in charming Richmond with Private Sauna and other modern touches

Top trending hotels in Chesterfield

Omni Richmond Hotel

Omni Richmond Hotel

4 out of 5
100 S 12th St Richmond VA
The price is NZ$331 per night from 5 Apr to 6 Apr
NZ$331
5 Apr - 6 Apr
includes taxes & fees
Stay at this business-friendly hotel in Richmond. Enjoy breakfast (surcharge), room service and a 24-hour fitness centre. Our guests praise the helpful staff ...
Opens in a new windowOmni Richmond Hotel
Graduate by Hilton Richmond

Graduate by Hilton Richmond

4 out of 5
301 West Franklin Street Richmond VA
The price is NZ$299 per night from 19 Apr to 20 Apr
NZ$299
19 Apr - 20 Apr
includes taxes & fees
Stay at this business-friendly hotel in Richmond. Enjoy free Wi-Fi, a rooftop terrace and breakfast (surcharge). Our guests praise the restaurant and the helpful ...
Opens in a new windowGraduate by Hilton Richmond
Drury Plaza Hotel Richmond

Drury Plaza Hotel Richmond

3 out of 5
11049 West Broad St Glen Allen VA
Fully refundableReserve now, pay when you stay
The price is NZ$259 per night from 16 Apr to 17 Apr
NZ$259
16 Apr - 17 Apr
includes taxes & fees
Stay at this business-friendly hotel in Glen Allen. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their ...
Opens in a new windowDrury Plaza Hotel Richmond
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The Jefferson Hotel

The Jefferson Hotel

5 out of 5
101 West Franklin Street Richmond VA
Fully refundableReserve now, pay when you stay
The price is NZ$641 per night from 5 Apr to 6 Apr
NZ$641
5 Apr - 6 Apr
includes taxes & fees
Stay at this luxury hotel in Richmond. Enjoy free Wi-Fi, 2 restaurants and 2 bars/lounges. Our guests praise the helpful staff and the comfy rooms in their reviews. ...
Opens in a new windowThe Jefferson Hotel
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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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^Subject to availability and chosen travel dates.