Holiday Homes in Chesterfield District

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Our top choices for Chesterfield District holiday homes

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
9.8 out of 10, Exceptional, (36 reviews)
"Gorgeous location, very comfortable accommodation would definitely stay there again!"
United Kingdom
Debbie R.
Cosy Barn in The Peak District National Park - ideal for walkers. Dog friendly .

Self Catering Holiday Bungalow in Ilam near Dovedale

Self Catering Holiday Bungalow in Ilam near Dovedale
Ashbourne
9.6 out of 10, Exceptional, (176 reviews)
"Great bungalow in a fantastic countryside location with comfortable beds and everything you need"
United Kingdom
Mark W.
Self Catering Holiday Bungalow in Ilam near Dovedale

Stone built self-catering lodge in stunning location

Stone built self-catering lodge in stunning location
Froggatt
10.0 out of 10, Exceptional, (10 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 £105
includes taxes & fees
2 Jun - 3 Jun
Stone built self-catering lodge in stunning location

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

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

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, (16 reviews)
"Great place for large groups "
Canada
Taylor C.
Perfect for all large groups in 7 all ensuite bedrooms . Pet friendly

The Gathering House – Large 6 Bedroom Victorian House, Walk to Buxton Centre

The Gathering House – Large 6 Bedroom Victorian House, Walk to Buxton Centre
Buxton
10.0 out of 10, Exceptional, (1 review)
"Host was super helpful, property location and inside the property was fantastic - would certainly recommend. "
United Kingdom
Thomas G.
The Gathering House – Large 6 Bedroom Victorian House, Walk to Buxton Centre

Beautiful Victorian house with stunning views of Matlock and the Derwent valley

Beautiful Victorian house with stunning views of Matlock and the Derwent valley
Matlock
10.0 out of 10, Exceptional, (9 reviews)
"Property exceeded expectations. Fantastic location / views; was extremely well equipped and clean. Perfect for our weekend get together with friends."
United States
Peter B.
Beautiful Victorian house with stunning views of Matlock and the Derwent valley

White Horse Cottage with Sauna

White Horse Cottage with Sauna
Wellow
9.2 out of 10, Wonderful, (13 reviews)
"Good property for a dog friendly cottage, had a great few nights but needs a bit of love but would return. The Maypole Inn does a lovely meal."
United Kingdom
Jayne B.
White Horse Cottage with Sauna

Host & Stay | Rock End

Host & Stay | Rock End
Matlock
9.6 out of 10, Exceptional, (8 reviews)
"Great house close to town and lovely country walks."
United Kingdom
Chris B.
Host & Stay | Rock End

3 Bedroom, Bright and Airy Bungalow in Monyash Village. Sleeps 6

3 Bedroom, Bright and Airy Bungalow in Monyash Village. Sleeps 6
Bakewell, Derbyshire
9.4 out of 10, Exceptional, (12 reviews)
"Great location"
United Kingdom
Steve H.
3 Bedroom, Bright and Airy Bungalow in Monyash Village. Sleeps 6

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.

5 Beds, 7 Guests, Private Garden, Free Parking

5 Beds, 7 Guests, Private Garden, Free Parking
3.5 star property
Nottingham
The price is £179
includes taxes & fees
2 Jun - 3 Jun
5 Beds, 7 Guests, Private Garden, Free Parking

Sheffield Serenity Retreat

Sheffield Serenity Retreat
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 £107
includes taxes & fees
31 May - 1 Jun
Sheffield Serenity Retreat

Fairview House - Celebration

Fairview House - Celebration
Tideswell
10.0 out of 10, Exceptional, (3 reviews)
"House was lovely and clean. It's a great house for hosting friends or family with perfect entertaining space.We would definitely book to return. "
United Kingdom
Daniel W.
Fairview House - Celebration

use With Modern Comforts

use With Modern Comforts
2.0 star property
Basford
The price is £177
includes taxes & fees
26 May - 27 May
use With Modern Comforts

Isimi luxurious 4 Bed House Derby, with ensuite bathrooms. A Home away from Home

Isimi luxurious 4 Bed House Derby, with ensuite bathrooms. A Home away from Home
Wessington
2.0 out of 10, (1 review)
"There was many things that were incredibly disappointing about this property. An hour before arriving we received a message to say the main bathroom toilet was blocked and they weren’t going to fix it before our stay, meaning the only toilets available were inside the 2 en-suite bathrooms. After arriving we found the house in what seemed to be mid construction. The kitchen was still covered in protective plastic, with cupboards without handles and a complete lack of cutlery, glasses and plates....
United Kingdom
Stephanie E.
The price is £338
includes taxes & fees
26 May - 27 May
Isimi luxurious 4 Bed House Derby, with ensuite bathrooms. A Home away from Home

Delightful House in the Heart of the Matlocks!

Delightful House in the Heart of the Matlocks!
Matlock
Delightful House in the Heart of the Matlocks!

Robin Hood Tower

Robin Hood Tower
3.0 star property
Matlock
10.0 out of 10, Exceptional, (12 reviews)
"It’s a really cute place to stay. Beautiful views and garden with a lovely canal side walk nearby. Nicely designed inside and Steve, the owner, is incredibly friendly and helpful. Would have liked to have been able to stay longer."
United Kingdom
Alex
The price is £210
includes taxes & fees
1 Jun - 2 Jun
Robin Hood Tower

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.
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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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 654 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
313
Accommodation
654 Holiday Homes
Lowest Price
£105
Highest Price
£338

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