A historic church with a tall spire, arched windows, and a clock tower.

Search Holiday Rentals in Chesterfield

Q: What are some of the best holiday rentals that Chesterfield has to offer?

Old Nags Head : This holiday home rental outside of Chesterfield comes with free WiFi so that you can feel at home during your trip. Kitchen amenities include a stovetop, a microwave and kitchenware.

Dates

November 2026

December 2026

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Our top choices for Chesterfield holiday rentals

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

1. The Old School House

Brimington

includes taxes & fees

8 Nov - 9 Nov

A patio with stone tiles, a wooden fence, and a flower bed with plants and flowers.

2. 2bed - Garden-pets-freeparking-m1connections

Chesterfield

Philip

includes taxes & fees

22 Nov - 23 Nov

A kitchen with white cabinets, a wooden beam ceiling, a microwave, and a wooden dining table.

3. Carr House Farm

Chesterfield

includes taxes & fees

17 Nov - 18 Nov

A wooden deck with two wicker sofas and a table, surrounded by a white lattice fence.

4. 2 bedroom accommodation in Holymoorside

Holymoorside

V & P Roberts

5. 2bed - garden-pets-freeparking-M1connections

Chesterfield

Ray W.

includes taxes & fees

22 Nov - 23 Nov

A dining area with a wooden table and chairs, a stone wall, and a view of the garden through a glass door.

6. Bathurst Cottage is a delightful three bedroom detached cottage.

Chesterfield

Valerie Thompson

includes taxes & fees

12 Nov - 13 Nov

A balcony with a view of a field, a table with chairs, and a potted plant.

7. Bryn Tor - The Gardener's House

Bolsover, near Chesterfield

includes taxes & fees

9 Nov - 10 Nov

A conservatory with a dining table set for six, surrounded by large windows offering a view of a garden.

8. Cherry Tree Farm

Chesterfield

includes taxes & fees

24 Nov - 25 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 stone building with a water wheel and a staircase.

10. Little Mill

Chesterfield

Rona

includes taxes & fees

14 Nov - 15 Nov

A cozy cabin-style interior with a kitchen, dining area, and seating space.

11. Thorntree Lodge

Chesterfield

includes taxes & fees

20 Nov - 21 Nov

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

12. Overton

Chesterfield

includes taxes & fees

17 Nov - 18 Nov

A bedroom with a bed, a television, a nightstand, and a bathroom visible through a doorway.

13. The Old Stables

Chesterfield

includes taxes & fees

15 Nov - 16 Nov

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

14. Cedar Cottage

Chesterfield

includes taxes & fees

15 Nov - 16 Nov

A rustic interior with exposed wooden beams, a stone wall, and a leather sofa.

15. The Loft

Chesterfield

includes taxes & fees

11 Nov - 12 Nov

A wooden deck with outdoor seating and a glass door leading to a covered area.

16. Harry's Lodge

Chesterfield

includes taxes & fees

20 Nov - 21 Nov

A cozy room with a wooden ceiling, a sofa, and a window with curtains.

17. Swallows Barn

Chesterfield

includes taxes & fees

13 Nov - 14 Nov

A stone house with a sloped roof, a green door, and a mailbox attached to the wall.

18. Woodthorpe Cruck Cottage

Chesterfield

Anthony

includes taxes & fees

3 Dec - 4 Dec

A stone building with a large window, a stone archway, and a garden with hedges and a flower bed.

19. The Tack Room Cottage

Chesterfield

includes taxes & fees

11 Nov - 12 Nov

A stone building with a pitched roof, a small porch, and a stone wall in the background.

20. Riber View Barn

Chesterfield

includes taxes & fees

20 Nov - 21 Nov

View all properties

Find holiday rentals that suit your style

Top Chesterfield Hotel Reviews

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

Bridleways Guest House & Holiday Homes

Mansfield

10/10 Excellent

Anonymous traveller

A nighttime garden with a water feature and a decorative fountain.

Home Farm & Lodge

Doncaster

10/10 Excellent

Richard

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

The Barrel Inn

Hope Valley

10/10 Excellent

Nick

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 covered patio, a lawn, and a dining area with a table and chairs.

Biggin Hall Hotel

Buxton

10/10 Excellent

Anonymous traveller

A stone building with multiple windows and a bench in front.

Pack Horse Inn

High Peak

10/10 Excellent

Mavis

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

The George - Hathersage

Hope Valley

10/10 Excellent

John

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

White Hart Inn

Alfreton

10/10 Excellent

Angela

A bar area with a wooden counter, red seating, and colorful hanging lights.

Bike & Boot Peak District

Hope Valley

10/10 Excellent

Dean

An indoor dining area with bamboo plants, tables, and chairs arranged for guests.

Hex Wildlife Hotel

Doncaster

10/10 Excellent

Rebekah

A hotel entrance with a brick facade, a sign reading "Motel Inn," and a paved walkway with bollards and potted plants.

Morley Hayes Hotel

Ilkeston

10/10 Excellent

Rachel

A restaurant with outdoor seating and two lion statues.

Best Western Premier Doncaster Mount Pleasant Hotel

Doncaster

10/10 Excellent

David

Find out more about Chesterfield

Everything you need to know about Chesterfield 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 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chesterfield holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesterfield. 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 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 holiday rentals we have selected for you start as low as £114 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chesterfield rentals

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

Frequently Asked Questions

Can I find a holiday rental in Chesterfield?

Yes, there are holiday rentals in Chesterfield close to Clay Cross Active, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Chesterfield has a good selection of top-notch restaurants and lively bars. Make sure you have time to check out the churches and parks during your trip.

What are some of the best holiday rentals that Chesterfield has to offer?

Old Nags Head: This holiday home rental outside of Chesterfield comes with free WiFi so that you can feel at home during your trip. Kitchen amenities include a stovetop, a microwave and kitchenware.

How many holiday rentals will I find in Chesterfield?

With 43 Expedia holiday rentals, you're guaranteed to find just the right place for your Chesterfield stay.

What can I see and do in Chesterfield?

Enjoy the outdoors at Peak District National Park and Queen's Park, or simply take in cultural attractions like Barrow Hill Roundhouse Railway Centre and Hotel Van Dyk Theater. Chesterfield Market and Bolsover Castle are other places to visit while you're in town.

What are holiday rentals like in Chesterfield?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chesterfield. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll feel right at home. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from shared hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for a family getaway.

Search Holiday Rentals in Chesterfield

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chesterfield holiday rentals

1. The Old School House

2. 2bed - Garden-pets-freeparking-m1connections

3. Carr House Farm

4. 2 bedroom accommodation in Holymoorside

5. 2bed - garden-pets-freeparking-M1connections

6. Bathurst Cottage is a delightful three bedroom detached cottage.

7. Bryn Tor - The Gardener's House

8. Cherry Tree Farm

9. Cherry Tree Cottage

10. Little Mill

11. Thorntree Lodge

12. Overton

13. The Old Stables

14. Cedar Cottage

15. The Loft

16. Harry's Lodge

17. Swallows Barn

18. Woodthorpe Cruck Cottage

19. The Tack Room Cottage

20. Riber View Barn

Find holiday rentals that suit your style

Top Chesterfield Hotel Reviews

The View at The White Horse Woolley Moor

10/10 Excellent

Find out more about Chesterfield

Chesterfield holiday rentals: An excellent choice for every season

How to find incredible deals on Chesterfield rentals

Frequently Asked Questions

Can I find a holiday rental in Chesterfield?

What are some of the best holiday rentals that Chesterfield has to offer?

How many holiday rentals will I find in Chesterfield?

What can I see and do in Chesterfield?

What are holiday rentals like in Chesterfield?

Explore a world of travel with Expedia