Chesterfield District Holiday Homes from £105: Search Holiday Homes in Chesterfield District

A town square with a prominent church steeple, a clock tower, and traditional half-timbered buildings.

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Our top choices for Chesterfield District holiday homes

A stone building with a sloped roof, a small porch, and a gravel driveway.

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

Alstonefield

Rebecca

2. Old Nags Head

Hope Valley

Kai

includes taxes & fees

28 Sept - 29 Sept

A stone building with a black door, a patio with a table and chairs, and a wooden fence.

3. Recently renovated 2 bedroom annexe with open plan living room and kitchen.

Stoney Middleton

Hugh C.

A living room with a brown leather sofa, patterned rug, and a fireplace.

4. Perfect for all large groups in 7 all ensuite bedrooms . Pet friendly

Buxton

Christopher H.

A stone building with a wooden picnic table and benches, surrounded by lush greenery and potted plants.

5. Self Catering Holiday Bungalow in Ilam near Dovedale, Ashbourne

Ashbourne

Debbie W.

includes taxes & fees

24 Sept - 25 Sept

A wooden shed with a bench inside, surrounded by a wooden fence and a grassy yard with scattered flowers.

6. Lovely 4 bedroom detached house in Southwell

Southwell

RS B.

A wooden cabin with a porch, a small garden area, and a gravel path leading to the entrance.

7. Peaceful Cabin in Skegby -sleeps2- Fire Pit

Sutton-in-Ashfield

Duncan

A compact kitchen with a bar stool, a built-in stove, and a window with blinds.

8. 4 Bed House - Sleeps 10 - Garden - Parking - Wifi

Doncaster

includes taxes & fees

2 Oct - 3 Oct

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Top Chesterfield District Hotel Reviews

Leopold Hotel

10/10 Excellent

"The leopard Hotel is fabulous the staff customer service was great the room was very good clean had a wonderful stay in centre of Sheffield The buffet breakfast was outstanding best I have ever had fresh ingredients would stay again 😁"

Old Hall Hotel

10/10 Excellent

"The building is absolutely beautiful and old. Located right in the middle, near the crescent and the pavillion gardens. The room was lovely. There were some areas which let it down. With dust on some carpet edges and dust on top of the curtains. Which are understandable given how tall the windows were. But these are more due to the fact it's an old building. The room was hot and I wasn't able to open the windows properly, but not too bad. Was worse when trying to get ready. Bed was super comfy. Breakfast was really nice. All staff were helpful and friendly. I would recommend and stay here again if I needed to stay over. Parking was outside, if you managed to get a space and you could get a pass for £6 for 24 hours. Overall I thought it was lovely."

Buxton Crescent

8/10 Good

"I have stayed at this hotel over 5 times under 2 different owners. The spa is always impressive however Champneys now charge extra for residents’ access per day. This results in a stampede at 3pm for guests wanting to (rightly) get their money’s worth. It really detracts from the ability to relax. The spa bar area could do with a little TLC: walls marked; carpets covered in crumbs; cobwebs on the ceiling alcoves; plastic champagne flutes!!! The bed was comfortable and the bedroom spacious. They no longer provide Buxton water however :( Breakfast was ok. The buffet section has been reduced and we couldn’t see any pastries. The cooked part was ok. Poached eggs were completely cooked through but not hot. The staff were great and the breakfast team in particular seemed more professional than previous visits. They were kind and courteous and efficient. My complaints are small but added together give an impression of tightness on the part of the hotel. Lastly, it’s the only hotel I have ever been to where the room is never ready early!"

Radisson Blu Hotel, Sheffield

8/10 Good

"The hotel is in a great location and the rooms were spotless, modern and comfortable. Breakfast was a nit haphazard. Tables were not available and there was no check in so you had to find your own way. The staff were very friendly and tried their best but they were somewhat overwhelmed. Also, there was a power outage on my second morning so no TV or power sockets were available but overall, it was a nice stay."

Find out more about Chesterfield District

Chesterfield District Holiday Homes: Find the Perfect Place

What is the best time to enjoy a holiday home in Chesterfield District?

It might be best to get a rental house in when the weather is ideal for enjoying local surroundings. If you go during the off-season months, there might be fewer tourists and often lower rates, like in .

How many holiday homes are available for rent in Chesterfield District?

Choose from 810 beautiful holiday homes in Chesterfield District for your getaway.

How much is a holiday home in Chesterfield District?

You can find perfect holiday homes in Chesterfield District for as low as £105 per night. Holiday home prices vary depending on what time of year you visit, whether the home is in the city centre or near popular sightseeing spots, and what kinds of amenities it offers.

How can I get the best deal on a holiday home in Chesterfield District?

Find the best deals on Chesterfield District holiday homes by entering dates and the number of travellers in the search bar. You can use the map feature to view prices and more specific locations of several accommodations all at once. Or filter your search results by star rating, price, number of bedrooms, types of amenities, and accessibility features—Expedia offers incredible deals for every budget.

Why should I book a holiday home in Chesterfield District?

There’s no better way to spend your well-earned holiday than in a private, cosy Chesterfield District holiday home. You’ll be able to fit all travellers in your group and have a place to call home while you explore Chesterfield District.

What amenities are available in a private holiday home?

Depending on your budget and the neighbourhood you choose, you’ll find amenities like a private pool, hot tub, free parking, a full-service kitchen or kitchenette, in-home laundry and WiFi. Your Chesterfield District holiday won’t be complete without a beautiful view and easy access to popular activities, use our filter to browse our offers.

Why should I book a holiday home with Expedia?

With Expedia, you’ll earn points on every booking and get incredible deals and member prices. Choose from a vast inventory of holiday homes in Chesterfield District—and book all your travel in one place. Save even more when you bundle your bookings together. Add a Chesterfield District car hire to your holiday property into a holiday package.

What are the cancellation and flexibility options?

We suggest using the “free cancellation” filter during your search to make sure your booking is flexible. Some accommodations accept and refund cancellations within a specific timeframe, while others may be non-refundable. Before you book, check your rental terms, or reach out to our customer service portal for further assistance.

Chesterfield District Holiday Homes information

Number of reviews	378
Accommodation	810 Holiday Homes
Lowest Price	£105
Highest Price	£220

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Chesterfield Holiday Rentals

Holiday Homes in Chesterfield District

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chesterfield District holiday homes

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

2. Old Nags Head

3. Recently renovated 2 bedroom annexe with open plan living room and kitchen.

4. Perfect for all large groups in 7 all ensuite bedrooms . Pet friendly

5. Self Catering Holiday Bungalow in Ilam near Dovedale, Ashbourne

6. Lovely 4 bedroom detached house in Southwell

7. Peaceful Cabin in Skegby -sleeps2- Fire Pit

8. 4 Bed House - Sleeps 10 - Garden - Parking - Wifi

9. Stone built self-catering lodge in stunning location

10. Delightful House in the Heart of the Matlocks!

11. The Acorn - Award Winning Barn Conversion In Hope Village Near To Castleton

12. 3 Bed House Sleeps 5 - Free Parking - Tv & Wifi

13. Luxury Peak District Cottage/Barn Derbyshire, Carsington Lake views WiFi

14. Derwent House ideal for groups or a special occasion. All prices fully inclusive

15. West Lodge, 5 Bedroom House, Dog Friendly, EV Charger + Great Location.

16. Diamond House, Sheffield: Lovely 3 bedroom centrally-located, industrial styled.

17. Charress House, 6/7 Bedrooms, 10 beds, 3 bathrooms Contractors/Friends/Families.

18. Commuters Getaway Chesterfield

19. a Quiet Semi Rural Property Located in Bolsover

20. Fairview House - Celebration

Find holiday rentals that suit your style

Top Chesterfield District Hotel Reviews

Leopold Hotel

Find out more about Chesterfield District

Chesterfield District Holiday Homes: Find the Perfect Place

What is the best time to enjoy a holiday home in Chesterfield District?

How many holiday homes are available for rent in Chesterfield District?

How much is a holiday home in Chesterfield District?

How can I get the best deal on a holiday home in Chesterfield District?

Why should I book a holiday home in Chesterfield District?

What amenities are available in a private holiday home?

Why should I book a holiday home with Expedia?

What are the cancellation and flexibility options?

Chesterfield District Holiday Homes information

Explore a world of travel with Expedia