Book Holiday Homes in Chesterfield

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Featured Holiday Homes in Chesterfield

Large Victorian 6 bed house in the centre of Matlock with hot tub and games room

Large Victorian 6 bed house in the centre of Matlock with hot tub and games room

Matlock
With a stay at this vacation home, you'll be centrally located in Matlock, within a 10-minute drive of Peak District National Park and Crown Square.
Large Victorian 6 bed house in the centre of Matlock with hot tub and games room
Cosy Barn in The Peak District National Park - ideal for walkers. Dog friendly .

Cosy Barn in The Peak District National Park - ideal for walkers. Dog friendly .

Alstonefield
With a stay at this vacation home in Ashbourne, you'll be within a 15-minute drive of Peak District National Park and Dovedale National Nature Reserve.
Cosy Barn in The Peak District National Park - ideal for walkers. Dog friendly .
Entire home in Nottingham

Entire home in Nottingham

Radford
The price is AU$278 per night from 7 Jan to 8 Jan
AU$278
includes taxes & fees
7 Jan - 8 Jan 2025
With a stay at this vacation home in Nottingham, you'll be a 5-minute drive from Motorpoint Arena Nottingham and 5 minutes from University of Nottingham.
Entire home in Nottingham
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Peak District Home with Garden and Parking

Peak District Home with Garden and Parking

Ashbourne
The price is AU$378 per night from 1 Jan to 2 Jan
AU$378
includes taxes & fees
1 Jan - 2 Jan 2025
With a stay at this vacation home in Ashbourne, you'll be within a 10-minute drive of Peak District National Park and Pipes in The Peaks.
Peak District Home with Garden and Parking
Bathmans Cottage - Newly refurbished Matlock house on edge of the Peak District

Bathmans Cottage - Newly refurbished Matlock house on edge of the Peak District

Matlock
With a stay at this vacation home, you'll be centrally located in Matlock, within a 15-minute drive of Peak District National Park and Chatsworth House.
Bathmans Cottage - Newly refurbished Matlock house on edge of the Peak District
Secluded 4 bed bungalow in mature 1 acre gardens with b close to Sherwood Forest

Secluded 4 bed bungalow in mature 1 acre gardens with b close to Sherwood Forest

Edingley
Located in Newark, this vacation home is in a rural location, within a 5-minute drive of Wheelgate Park and Oakmere Park Golf Club.
Secluded 4 bed bungalow in mature 1 acre gardens with b close to Sherwood Forest
Elegant Retreat Nook at Peak District Gateway

Elegant Retreat Nook at Peak District Gateway

Totley
Located in Sheffield, this vacation home is within a 15-minute drive of University of Sheffield and Peak District National Park.
Elegant Retreat Nook at Peak District Gateway
Acer Cottage Tideswell village Buxton pets welcome dog friendly. Parking 2 cars

Acer Cottage Tideswell village Buxton pets welcome dog friendly. Parking 2 cars

Tideswell
With a stay at this vacation home in Buxton, you'll be within a 15-minute drive of Peak District National Park and Tideswell School of Food.
Acer Cottage Tideswell village Buxton pets welcome dog friendly. Parking 2 cars
Apartment in Derby by Leecroft Cosy Stays

Apartment in Derby by Leecroft Cosy Stays

Alvaston
Located in Derby (Alvaston), this vacation home is within a 5-minute drive of The Derby Conference Centre and The Roundhouse.
Apartment in Derby by Leecroft Cosy Stays
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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
855 Holiday Homes
Lowest Price
AU$68
Highest Price
AU$378
Popular accommodation
Large Victorian 6 bed house in the centre of Matlock with hot tub and games room, Cosy Barn in The Peak District National Park - ideal for walkers. Dog friendly ., Entire home in Nottingham, Peak District Home with Garden and Parking, Bathmans Cottage - Newly refurbished Matlock house on edge of the Peak District, Secluded 4 bed bungalow in mature 1 acre gardens with b close to Sherwood Forest, Elegant Retreat Nook at Peak District Gateway, Acer Cottage Tideswell village Buxton pets welcome dog friendly. Parking 2 cars, Apartment in Derby by Leecroft Cosy Stays

Top trending hotels in Chesterfield

Casa Hotel

Casa Hotel

4 out of 5
Lockoford Lane, Chesterfield, England
Fully refundableReserve now, pay when you stay
The price is AU$282 per night from 29 Dec to 30 Dec
AU$282
includes taxes & fees
29 Dec - 30 Dec
With a stay at Casa Hotel in Chesterfield, you'll be within a 15-minute drive of Peak District National Park and Technique Stadium.
Casa Hotel
WILDES INNS

WILDES INNS

4 out of 5
Worksop Road, Clowne, Chesterfield, England
Fully refundableReserve now, pay when you stay
The price is AU$179 per night from 29 Dec to 30 Dec
AU$179
includes taxes & fees
29 Dec - 30 Dec
Located in Chesterfield, WILDES INNS is in the historical district, within a 10-minute drive of Rother Valley Country Park and Creswell Crags.
WILDES INNS
Ringwood Hall Hotel & Spa

Ringwood Hall Hotel & Spa

4 out of 5
Chesterfield Road, Chesterfield, England
Fully refundableReserve now, pay when you stay
The price is AU$141 per night from 9 Jan to 10 Jan
AU$141
includes taxes & fees
9 Jan - 10 Jan 2025
Located in Chesterfield, Ringwood Hall Hotel & Spa is in the suburbs, a 5-minute drive from Pomegranate Theatre and 5 minutes from Technique Stadium.
Ringwood Hall Hotel & Spa
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ibis Chesterfield North - Barlborough

ibis Chesterfield North - Barlborough

3 out of 5
3 Tallys End, Chesterfield Road, Chesterfield, England
Fully refundableReserve now, pay when you stay
The price is AU$68 per night from 12 Jan to 13 Jan
AU$68
includes taxes & fees
12 Jan - 13 Jan 2025
With a stay at ibis Chesterfield North - Barlborough in Chesterfield, you'll be within a 5-minute drive of Hotel Van Dyk Theater and Renishaw Hall.
ibis Chesterfield North - Barlborough
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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.