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

Holiday Homes in Chesterfield District

Compare and save
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Save instantly and earn perks with One Key
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Chesterfield District holiday homes

1. 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
10.0 out of 10, Exceptional, (43 reviews)
"Second time staying here, had an amazing stay, and no complaints. "
United Kingdom
Jasmine P.
Cosy Barn in The Peak District National Park - ideal for walkers. Dog friendly .

2. Peaceful Cabin in Skegby -sleeps2- Fire Pit

Peaceful Cabin in Skegby -sleeps2- Fire Pit
3.5 star property
Sutton-in-Ashfield
9.0 out of 10, Wonderful, (2 reviews)
"Amazing place! Stayed on my own whilst working away. Nice and peaceful. Lovely hosts. Very private. Very new and well kitted out. "
United Kingdom
Duncan
Peaceful Cabin in Skegby -sleeps2- Fire Pit

3. Lovely 4 bedroom detached house in Southwell

Lovely 4 bedroom detached house in Southwell
Southwell
10.0 out of 10, Exceptional, (17 reviews)
"Very nice house in a quiet neighborhood. Just right for family."
United States
RS B.
Lovely 4 bedroom detached house in Southwell

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

Self Catering Holiday Bungalow in Ilam near Dovedale, Ashbourne
Ashbourne
9.6 out of 10, Exceptional, (177 reviews)
"A true gem! Thoroughly enjoyed our stay here and will definitely be booking again. Wonderful!"
United States
Debbie W.
Self Catering Holiday Bungalow in Ilam near Dovedale, Ashbourne

5. 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
8.0 out of 10, Very good, (19 reviews)
"Good functional base for a large group and suitably equipped for cooking meals for large groups. A little dated and well used however no issues and comparably cheap for the region."
United Kingdom
Christopher H.
Perfect for all large groups in 7 all ensuite bedrooms . Pet friendly

6. Stone built self-catering lodge in stunning location

Stone built self-catering lodge in stunning location
Froggatt
10.0 out of 10, Exceptional, (11 reviews)
"Amazing location enjoyed every minute we stayed here Katie and Rod were very friendly beautiful little cottage"
United Kingdom
Michelle C.
The price is £120
includes taxes & fees
20 Aug - 21 Aug
Stone built self-catering lodge in stunning location

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

Derwent House ideal for groups or a special occasion. All prices fully inclusive
Matlock
8.0 out of 10, Very good, (2 reviews)
"Great location with lots to do on your doorstep."
United States
Christian C.
Derwent House ideal for groups or a special occasion. All prices fully inclusive

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

West Lodge, 5 Bedroom House, Dog Friendly, EV Charger + Great Location.
Buxton
10.0 out of 10, Exceptional, (2 reviews)
"All questions were responded to quickly to help us have a great stay. Accommodation was comfortable, and great location. "
United Kingdom
Tony B.
West Lodge, 5 Bedroom House, Dog Friendly, EV Charger + Great Location.

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

The Acorn - Award Winning Barn Conversion In Hope Village Near To Castleton
Hope
9.8 out of 10, Exceptional, (36 reviews)
"Great location !"
United Kingdom
Super C.
The Acorn - Award Winning Barn Conversion In Hope Village Near To Castleton

10. Fairview House - Celebration

Fairview House - Celebration
Tideswell
10.0 out of 10, Exceptional, (4 reviews)
"Fantastic house and garden. Beautiful and very well equipped kitchen. From the house, you can enjoy many wonderful walks, especially if you're willing to drive for about 15 minutes. For example, Mam Tor and several other beautiful hiking routes are nearby. There's also an excellent farm shop just 20 minutes away. Highly recommended!"
United States
Ellen D.
Fairview House - Celebration

11. Forest Farm Papplewick Nottingham - Spacious Self-Contained Rural Retreat!

Forest Farm Papplewick Nottingham - Spacious Self-Contained Rural Retreat!
Papplewick, Nottinghamshire
10.0 out of 10, Exceptional, (12 reviews)
"Lovely place to stay with easy access to family in Mansfield. Comfortable bed, sufficiently fast WIFI, and well appointed!"
United States
Fran B.
Forest Farm Papplewick Nottingham - Spacious Self-Contained Rural Retreat!

12. a Quiet Semi Rural Property Located in Bolsover

a Quiet Semi Rural Property Located in Bolsover
3.5 star property
Chesterfield
The price is £126
includes taxes & fees
9 Aug - 10 Aug
a Quiet Semi Rural Property Located in Bolsover

13. 2bed - garden-pets-freeparking-M1connections

2bed - garden-pets-freeparking-M1connections
Chesterfield
7.4 out of 10, Good, (3 reviews)
"It was in a good location plenty of amenities close by "
United Kingdom
Ray W.
The price is £111
includes taxes & fees
12 Aug - 13 Aug
2bed - garden-pets-freeparking-M1connections

14. Charming Riverside Cottage in Bradwell, Central Peak District | 4 Guests

Charming Riverside Cottage in Bradwell, Central Peak District | 4 Guests
Bradwell
9.8 out of 10, Exceptional, (113 reviews)
"Lovely property in a great location."
United Kingdom
Bill D.
Charming Riverside Cottage in Bradwell, Central Peak District | 4 Guests

15. Charress House, 5/6 Bedrooms, 9 beds, 3 bathrooms Contractors/Friends/Families.

Charress House, 5/6 Bedrooms, 9 beds, 3 bathrooms Contractors/Friends/Families.
Whitwell
Charress House, 5/6 Bedrooms, 9 beds, 3 bathrooms Contractors/Friends/Families.

16. 3 Bed House Sleeps 5 - Free Parking - Tv & Wifi

3 Bed House Sleeps 5 - Free Parking - Tv & Wifi
3.0 star property
Sheffield
6.0 out of 10, (1 review)
"Overall if you are a dirtbag climber and just in sheffield for a quick trip this place totally gets the job done. Our biggest issues were that there was no shower curtain so the bathroom flooded when anyone showered, none of the bathrooms had soap, and overall just super limited amenities. Also the trash out front was absolutely overflowing and was all over the yard. Honestly would stay again in a pinch, just would come with lower expectations."
United Kingdom
Elizabeth
The price is £139
includes taxes & fees
9 Aug - 10 Aug
3 Bed House Sleeps 5 - Free Parking - Tv & Wifi

17. Split Level Bungalow - Sleeps4 - Close to Walks

Split Level Bungalow - Sleeps4 - Close to Walks
3.0 star property
Sutton-in-Ashfield
10.0 out of 10, Exceptional, (2 reviews)
"Probably the cleanest property ive ever stayed in and a lovely place with a lovely view (very comfy beds) nice extra touches like a welcome pack of treats and board games to play in the evenings. Would stay again! "
United Kingdom
sarah
Split Level Bungalow - Sleeps4 - Close to Walks

18. 2 Bed House - Sleeps 4 - Pets - Garden - Parking

2 Bed House - Sleeps 4 - Pets - Garden - Parking
3.0 star property
Newark
10.0 out of 10, Exceptional, (8 reviews)
"Lovely house, super clean and comfortable. Kitchen really well equipped, everything needed for a stay, milk and orange juice in the fridge on arrival. Perfect for our dog, Freddie, too. Wish we could have stayed longer! "
United Kingdom
Kate
The price is £124
includes taxes & fees
26 Aug - 27 Aug
2 Bed House - Sleeps 4 - Pets - Garden - Parking

19. Traditional 5 bedroom stone built farmhouse, near Monsal Trail and Bakewell.

Traditional 5 bedroom stone built farmhouse, near Monsal Trail and Bakewell.
Bakewell
9.4 out of 10, Exceptional, (3 reviews)
"Great property in a lovely setting. Very comfortable - like a home from home "
United Kingdom
Wendy B.
Traditional 5 bedroom stone built farmhouse, near Monsal Trail and Bakewell.

20. Delightful House in the Heart of the Matlocks!

Delightful House in the Heart of the Matlocks!
Matlock
10.0 out of 10, Exceptional, (1 review)
"On stepping in to the house , you immeadiatly get a feeling of....home. Its beautifully quirkly decorated, pet and family friendly, very clean and has everything and more you would need for a lovely stay in Matlock. Makes for an ideal centre location to explore th Peak District. Would definitly return and recommend to other people."
United Kingdom
carolyn
Delightful House in the Heart of the Matlocks!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chesterfield District Hotel Reviews

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 836 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 £111 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
269
Accommodation
836 Holiday Homes
Lowest Price
£111
Highest Price
£139

Explore a world of travel with Expedia