Book Holiday Homes in Chesterfield

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Featured Holiday Homes in Chesterfield

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

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

Whaley Bridge England
Located in High Peak, this vacation home is in a rural location, a 2-minute drive from Bugsworth Basin and 6 minutes from Church Lane.
Opens in a new windowHoneysuckle Cottage, 2 bed, sleeps 3, family-friendly and pet-friendly
Stunning House - Sleeps 7 - BUXTON - pet friendly

Stunning House - Sleeps 7 - BUXTON - pet friendly

Buxton Derbyshire
With a stay at this vacation home in Buxton, you'll be within a 5-minute drive of Peak District National Park and Buxton and Poole's Cavern Country Park.
Opens in a new windowStunning House - Sleeps 7 - BUXTON - pet friendly
Spacious Ensuite 2-Bedroom Flat in Kelham Island

Spacious Ensuite 2-Bedroom Flat in Kelham Island

Sheffield England
The price is AU$312 per night from 5 Jan to 6 Jan
AU$312
5 Jan - 6 Jan 2026
includes taxes & fees
With a stay at this vacation home in Sheffield, you'll be within a 10-minute drive of Peak District National Park and Paradise Square.
Opens in a new windowSpacious Ensuite 2-Bedroom Flat in Kelham Island
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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 England
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.
Opens in a new windowCosy Barn in The Peak District National Park - ideal for walkers. Dog friendly .
Studio Self contained flat free Parking

Studio Self contained flat free Parking

2 out of 5
4 Wyville Cl Nottingham England
The price is AU$98 per night from 30 Dec to 31 Dec
AU$98
30 Dec - 31 Dec
includes taxes & fees
With a stay at this vacation home in Nottingham, you'll be within a 5-minute drive of University of Nottingham and Motorpoint Arena Nottingham.
Opens in a new windowStudio Self contained flat free Parking
Cosy Cottage for 6 & Pets Friendly in Hope Valley| Pass the Keys

Cosy Cottage for 6 & Pets Friendly in Hope Valley| Pass the Keys

Stoney Middleton
With a stay at this vacation home in Hope Valley, you'll be within a 15-minute drive of Peak District National Park and Chatsworth House.
Opens in a new windowCosy Cottage for 6 & Pets Friendly in Hope Valley| Pass the Keys
Lovely 4 bedroom detached house in Southwell

Lovely 4 bedroom detached house in Southwell

Southwell England
With a stay at this vacation home in Southwell, you'll be within a 15-minute walk of Southwell Workhouse and Southwell Library.
Opens in a new windowLovely 4 bedroom detached house in Southwell
Perfect for all Large Groups in 7 all Ensuite Bedrooms . Pet Friendly

Perfect for all Large Groups in 7 all Ensuite Bedrooms . Pet Friendly

Buxton England
With a stay at this vacation home in Buxton, you'll be within a 5-minute drive of Peak District National Park and Tideswell School of Food.
Opens in a new windowPerfect for all Large Groups in 7 all Ensuite Bedrooms . Pet Friendly
Beautiful riverside village cottage in the heart of the Peak District

Beautiful riverside village cottage in the heart of the Peak District

Bradwell ENG
With a stay at this vacation home in Hope Valley, you'll be on the waterfront, within a 15-minute drive of Peak District National Park and Castleton Museum.
Opens in a new windowBeautiful riverside village cottage in the heart of the Peak District
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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
979 Holiday Homes
Lowest Price
AU$98
Highest Price
AU$312
Popular accommodation
Honeysuckle Cottage, 2 bed, sleeps 3, family-friendly and pet-friendly, Stunning House - Sleeps 7 - BUXTON - pet friendly , Spacious Ensuite 2-Bedroom Flat in Kelham Island, Cosy Barn in The Peak District National Park - ideal for walkers. Dog friendly ., Studio Self contained flat free Parking, Cosy Cottage for 6 & Pets Friendly in Hope Valley| Pass the Keys, Lovely 4 bedroom detached house in Southwell, Perfect for all Large Groups in 7 all Ensuite Bedrooms . Pet Friendly, Beautiful riverside village cottage in the heart of the Peak District

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$195 per night from 1 Jan to 2 Jan
AU$195
1 Jan - 2 Jan 2026
includes taxes & fees
Located in Chesterfield, Ringwood Hall Hotel & Spa is in the suburbs, a 5-minute drive from Pomegranate Theatre and 5 minutes from SMH Group Stadium.
Opens in a new windowRingwood Hall Hotel & Spa
WILDES INNS

WILDES INNS

4 out of 5
Worksop Road Chesterfield England
Fully refundableReserve now, pay when you stay
Located in Chesterfield, WILDES INNS is in the historical district, within a 10-minute drive of Rother Valley Country Park and Creswell Crags.
Opens in a new windowWILDES INNS
Twin Oaks Hotel

Twin Oaks Hotel

3 out of 5
Church Lane Chesterfield England
The price is AU$181 per night from 30 Dec to 31 Dec
AU$181
30 Dec - 31 Dec
includes taxes & fees
Located in Chesterfield, Twin Oaks Hotel is within a 10-minute drive of Hardwick Hall-Derbyshire Country Park and The Herb Garden.
Opens in a new windowTwin Oaks Hotel
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The Orchard Hotel & Restaurant

The Orchard Hotel & Restaurant

4 out of 5
Beeston Lane, University Park Nottingham England
When you stay at The Orchard Hotel & Restaurant in Nottingham, you'll be connected to the convention center, a 3-minute drive from University of Nottingham and ...
Opens in a new windowThe Orchard Hotel & Restaurant
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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.