Book Holiday Homes in Chesterfield

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Featured Holiday Homes in Chesterfield

Haddon Villa in centre of Bakewell, Peak District. Nr Chatsworth. Pet friendly

Haddon Villa in centre of Bakewell, Peak District. Nr Chatsworth. Pet friendly

Bakewell
With a stay at this vacation home in Bakewell, you'll be within a 10-minute drive of Peak District National Park and Chatsworth House.
Haddon Villa in centre of Bakewell, Peak District. Nr Chatsworth. Pet friendly
Self Catering Holiday Cottage in Ilam

Self Catering Holiday Cottage in Ilam

Ashbourne
The price is AU$317 per night from 8 May to 9 May
AU$317
includes taxes & fees
8 May - 9 May
When you stay at this vacation home in Ashbourne, you'll be on a river, within a 15-minute drive of Peak District National Park and Alton Towers.
Self Catering Holiday Cottage in Ilam
Honeysuckle Cottage, 2 bed, sleeps 3, family-friendly and pet-friendly

Honeysuckle Cottage, 2 bed, sleeps 3, family-friendly and pet-friendly

Whaley Bridge
With a stay at this vacation home in High Peak, you'll be within a 10-minute drive of Peak District National Park and Bugsworth Basin.
Honeysuckle Cottage, 2 bed, sleeps 3, family-friendly and pet-friendly
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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 .
Newly refurbished luxury 5 bed riverside house with hot tub and annexe.

Newly refurbished luxury 5 bed riverside house with hot tub and annexe.

Darley Bridge
When you stay at this vacation home in Matlock, you'll be on the waterfront, within a 15-minute drive of Peak District National Park and Chatsworth House.
Newly refurbished luxury 5 bed riverside house with hot tub and annexe.
Brook cottage in Baslow next to Chatsworth Park

Brook cottage in Baslow next to Chatsworth Park

Baslow
Located in Bakewell, this vacation home is in a rural location, within a 10-minute drive of Peak District National Park and Chatsworth House.
Brook cottage in Baslow next to Chatsworth Park
Marina view cottage - Canalside cottage - Peak District location

Marina view cottage - Canalside cottage - Peak District location

Furness Vale
The price is AU$349 per night from 5 May to 6 May
AU$349
includes taxes & fees
5 May - 6 May
With a stay at this vacation home in High Peak, you'll be on a river, within a 10-minute drive of Peak District National Park and Church Lane.
Marina view cottage - Canalside cottage - Peak District location
3 Bedroom, Bright and Airy Bungalow in Monyash Village sleeps 6

3 Bedroom, Bright and Airy Bungalow in Monyash Village sleeps 6

Bakewell
Located in Bakewell, this vacation home is within a 15-minute drive of Peak District National Park and Chatsworth House.
3 Bedroom, Bright and Airy Bungalow in Monyash Village sleeps 6
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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
1124 Holiday Homes
Lowest Price
AU$74
Highest Price
AU$349
Popular accommodation
Haddon Villa in centre of Bakewell, Peak District. Nr Chatsworth. Pet friendly, Self Catering Holiday Cottage in Ilam, Honeysuckle Cottage, 2 bed, sleeps 3, family-friendly and pet-friendly, 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 ., Newly refurbished luxury 5 bed riverside house with hot tub and annexe., Brook cottage in Baslow next to Chatsworth Park, Marina view cottage - Canalside cottage - Peak District location, 3 Bedroom, Bright and Airy Bungalow in Monyash Village sleeps 6

Top trending hotels in Chesterfield

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$147 per night from 1 Jun to 2 Jun
AU$147
includes taxes & fees
1 June - 2 June
Located in Chesterfield, Ringwood Hall Hotel & Spa is in the suburbs, a 4-minute drive from Poolsbrook Country Park and 5 minutes from Technique Stadium.
Ringwood Hall Hotel & Spa
WILDES INNS

WILDES INNS

4 out of 5
Worksop Road, Clowne, Chesterfield, England
Fully refundableReserve now, pay when you stay
The price is AU$212 per night from 14 May to 15 May
AU$212
includes taxes & fees
14 May - 15 May
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
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$74 per night from 26 May to 27 May
AU$74
includes taxes & fees
26 May - 27 May
With a stay at ibis Chesterfield North - Barlborough in Chesterfield, you'll be within a 15-minute drive of Meadowhall Shopping Centre and Hotel Van Dyk ...
ibis Chesterfield North - Barlborough
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ibis Chesterfield Centre – Market Town

ibis Chesterfield Centre – Market Town

3 out of 5
Lordsmill Street, North East Derbyshire, Chesterfield, England
Fully refundableReserve now, pay when you stay
The price is AU$75 per night from 18 May to 19 May
AU$75
includes taxes & fees
18 May - 19 May
With a stay at ibis Chesterfield Centre – Market Town in Chesterfield, you'll be within a 15-minute drive of Peak District National Park and Queen's Park.
ibis Chesterfield Centre – Market Town
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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.