A church with a tall spire and two clocks on its tower.

Search Holiday Rentals in Chesterfield District

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Dates

November 2026

December 2026

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Top cities in Chesterfield District

Railway tracks surrounded by greenery and trees.

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In two weeks

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In four months

Our top choices for Chesterfield District holiday rentals

A brick building with a wooden fence, a paved path, and a bicycle.

1. The Old School House

Brimington

includes taxes & fees

12 Nov - 13 Nov

A sunlit room with a large window, a sofa, a table, and a potted plant.

2. Overton

Chesterfield

includes taxes & fees

16 Nov - 17 Nov

A bedroom with a bed, a nightstand, a chair, a window with curtains, and a door.

3. Cedar Cottage

Chesterfield

includes taxes & fees

15 Nov - 16 Nov

A building with a stone facade, a balcony with outdoor seating, and a clear sky.

4. Rock Mill Retreat

Stoney Middleton

Gabriela

includes taxes & fees

1 Dec - 2 Dec

A modern loft bedroom with a sloped ceiling, a black leather sofa, a wooden chair, and a TV stand.

5. Relaxing En-Suite Apartment with Private Lounge, Kitchen and Parking

Nether Edge

Adam

includes taxes & fees

12 Nov - 13 Nov

A hotel room with a bed, a window with curtains, a radiator, and a door leading to a bathroom.

6. Kingfield Boutique Hotel

Nether Edge

Caroline

includes taxes & fees

12 Nov - 13 Nov

A dining area with a table set for four, a large window with a view of a red brick building, and a painting of a coastal landscape.

7. North Gate House

Sheffield City Centre

includes taxes & fees

23 Nov - 24 Nov

A compact kitchen with a microwave, sink, and dark cabinets. There's a wooden door leading to another room and a sofa in the corner.

8. Meadow View - (Bottom Cabin) - sleeps 2 guests in 1 bedroom

Foolow

Michael

includes taxes & fees

16 Nov - 17 Nov

A hot tub under a wooden pergola with a stone wall and greenery in the background.

9. Cherry Tree Cottage

Chesterfield

Lorraine

includes taxes & fees

22 Nov - 23 Nov

A cozy room with a dark blue sofa, a wooden wall with a 'NEWSPAPER' sign, a small wooden cabinet, and a window with a view of the outside.

10. Houseboat Hotels

Sheffield

Wendy

includes taxes & fees

22 Nov - 23 Nov

Three wine glasses on a wooden table with a house and greenery in the background.

11. Charming Cottage in Grindleford, Peak District

Grindleford

Alison H.

includes taxes & fees

15 Nov - 16 Nov

A cozy room with a bed, a sofa, a desk, and a window with curtains.

12. Hare’s Retreat - ( Middle Cabin ) - sleeps 2 guests in 1 bedroom

Foolow

Michael

includes taxes & fees

12 Nov - 13 Nov

A modern restaurant interior with large windows, tables, and chairs.

13. Sheffield Metropolitan by Belvilla - Standard Double Room

Sheffield

Anonymous traveller

includes taxes & fees

1 Dec - 2 Dec

A room with exposed wooden beams, a flat-screen TV mounted on the wall, and three hanging light bulbs.

14. Three Cranes Serviced Apartments

Sheffield City Centre

Graham

includes taxes & fees

15 Nov - 16 Nov

A dining table set with plates, cutlery, and a fruit bowl, surrounded by colorful chairs.

15. Spacesavers

Sheffield City Centre

Lynsey

includes taxes & fees

15 Nov - 16 Nov

A stone building with a green door, a window, and a small balcony.

16. Beautiful Cottage in Bradwell, Peak District

Bradwell

Bill D.

includes taxes & fees

19 Nov - 20 Nov

A modern apartment with a kitchen, a living area with a sofa and a bright orange chair, large windows, and artwork on the walls.

17. The Nest

Sheffield City Centre

Sharon

includes taxes & fees

12 Nov - 13 Nov

18. Old Nags Head

Hope Valley

includes taxes & fees

15 Nov - 16 Nov

A stone building with a water wheel and a staircase.

19. Little Mill

Chesterfield

Rona

includes taxes & fees

14 Nov - 15 Nov

A modern kitchen with white cabinets, a stainless steel range hood, a washing machine, and a dining area with a glass table set for two.

20. No2

Mansfield

J M

includes taxes & fees

15 Nov - 16 Nov

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Find holiday rentals that suit your style

Top Chesterfield District Hotel Reviews

A building with illuminated windows and a heart-shaped sculpture.

The Peacock at Barlow

Dronfield

10/10 Excellent

Rabia

A modern hotel room with a large bed, a sofa, a coffee table, and a TV. The room has large windows with curtains and a view of the outdoors.

The View at The White Horse Woolley Moor

Alfreton

10/10 Excellent

We booked a 2 night stay here to celebrate my wife's birthday , we wanted a relaxing weekend and the white horse seemed to offer what we were looking for . Right from check-in i realised we had definitely picked the right place . We received a warm and friendly welcome and were shown to our room . We picked a junior suit and there was nothing junior about it. We found it big , bright and offered everything we wanted . Very clean and well presented. Staff at the white horse are fantastic, ...

Anonymous traveller

A buffet setup with various food items and serving utensils.

Olde House, Chesterfield by Marston's Inns

Chesterfield

10/10 Excellent

Anonymous traveller

A rustic interior with a wooden dining table, chairs, a bar area with a wine rack, and a fireplace.

The Pilsley Inn

Bakewell

10/10 Excellent

Lovely characterful hotel in a great location. We were upgraded in to a four poster room. Although the bed dominated the room there was still room for a sofa, desk and chairs. In addition there was a very spacious ensuite with a modern finish and great fittings. The staff were very welcoming and keen to help. The villagers of Pilsley were very friendly. Just up the road is the Chatsworth Estate Farm Shop which has a brilliant selection of foodstuffs for those wanting the odd snack, souvenirs...

Beth

A modern bar area with a curved ceiling, bar stools, and a long counter with bottles.

Courtyard By Marriott Sheffield

Sheffield

10/10 Excellent

Alex

A large, historic house with a well-manicured garden, including a pond and various plants.

Fischers Baslow Hall

Bakewell

10/10 Excellent

Anonymous traveller

A stone fireplace with a rustic design, a wooden ceiling, and a patterned rug.

The Manor House

Dronfield

10/10 Excellent

Anonymous traveller

An outdoor patio with tables and chairs, surrounded by plants and umbrellas.

The Plough Inn

Hope Valley

10/10 Excellent

Anonymous traveller

A stone building with a black door and windows, labeled "The George."

The George - Hathersage

Hope Valley

10/10 Excellent

John

A spacious patio area with a dining table, chairs, and a sofa. There are potted plants and a large window with bamboo shades.

Cavendish Hotel

Bakewell

10/10 Excellent

Anonymous traveller

A cozy pub with a wooden interior, a fireplace, and traditional decor.

The Barrel Inn

Hope Valley

10/10 Excellent

Nick

A rustic wooden bed with a headboard, white bedding, and a fluffy white throw.

White Hart Inn

Alfreton

10/10 Excellent

Angela

A wooden interior with a hanging light fixture and a wooden bench.

The Horse & Jockey Wessington

Alfreton

10/10 Excellent

This is truly a wonderful hotel to stay I've stayed in hundreds of hotels This is in my top 3 to stay in If I'm ever working in Sheffield area again. I'll have no hesitation in booking this wonderful hotel The food is so well presented and taste delicious. Also I would like to make a serious point that the staff are so helpful polite and above all can't do enough for you It so wonderful Five stars to all

graham

A modern indoor pool area with a hot tub, lounge chairs, and a glass-enclosed upper level.

Ringwood Hall Hotel & Spa, BW Signature Collection

Chesterfield

10/10 Excellent

Michael

A bed with a headboard, two bedside tables, and pillows.

Bridleways Guest House & Holiday Homes

Mansfield

10/10 Excellent

Anonymous traveller

A bar area with a brick fireplace, wooden bar counter, and hanging light fixtures.

The Devonshire Arms Baslow

Bakewell

10/10 Excellent

Andrew

An outdoor patio area with wooden tables and chairs, umbrellas, and a gazebo.

The Maynard

Grindleford

10/10 Excellent

Joanna

Find out more about Chesterfield District

Everything you need to know about Chesterfield District 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 District holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 District holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Chesterfield District holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesterfield District. 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesterfield District 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 District holiday rentals we have selected for you start as low as £37 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chesterfield District rentals

At Expedia, we put the best Chesterfield District 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 District 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 District 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 District. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Search Holiday Rentals in Chesterfield District

Change your mind

Treat yourself

Be picky

Top cities in Chesterfield District

Staveley

Check prices for these dates

Our top choices for Chesterfield District holiday rentals

1. The Old School House

2. Overton

3. Cedar Cottage

4. Rock Mill Retreat

5. Relaxing En-Suite Apartment with Private Lounge, Kitchen and Parking

6. Kingfield Boutique Hotel

7. North Gate House

8. Meadow View - (Bottom Cabin) - sleeps 2 guests in 1 bedroom

9. Cherry Tree Cottage

10. Houseboat Hotels

11. Charming Cottage in Grindleford, Peak District

12. Hare’s Retreat - ( Middle Cabin ) - sleeps 2 guests in 1 bedroom

13. Sheffield Metropolitan by Belvilla - Standard Double Room

14. Three Cranes Serviced Apartments

15. Spacesavers

16. Beautiful Cottage in Bradwell, Peak District

17. The Nest

18. Old Nags Head

19. Little Mill

20. No2

Find holiday rentals that suit your style

Top Chesterfield District Hotel Reviews

The Peacock at Barlow

10/10 Excellent

Find out more about Chesterfield District

Chesterfield District holiday rentals: An excellent choice for every season

How to find incredible deals on Chesterfield District rentals

Explore a world of travel with Expedia