Holiday Homes in Chesterfield District

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Our top choices for Chesterfield District holiday homes

Large Victorian Family Home | Central Matlock | Hot Tub & Games Room | 13 Guests

Large Victorian Family Home | Central Matlock | Hot Tub & Games Room | 13 Guests
Matlock
9.8 out of 10, Exceptional, (99 reviews)
"This home was perfect for our family stayIt's immaculately clean. So convenient to the town of Matlock. Dan was a pleasure to work with and responded to any questions promptly. Our family would highly recommend this property "
United Kingdom
coral t.
Large Victorian Family Home | Central Matlock | Hot Tub & Games Room | 13 Guests

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, (32 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 .

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

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

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

Self contained Bungalow on the edge of Sherwood Forest .

Self contained Bungalow on the edge of Sherwood Forest .
Warsop
10.0 out of 10, Exceptional, (3 reviews)
"Lovely place to stay, immaculately clean and very friendly hosts. We stayed for one night to break up a long drive with young children and it was perfect. "
United Kingdom
Jenna G.
The price is £151
includes taxes & fees
10 Apr - 11 Apr
Self contained Bungalow on the edge of Sherwood Forest .

Self Catering Holiday Bungalow in Ilam near Dovedale

Self Catering Holiday Bungalow in Ilam near Dovedale
Ashbourne
9.6 out of 10, Exceptional, (173 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

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

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

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

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

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, (1 review)
"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.

Bankside Cottage, Milldale – Cosy Peak District Holiday Cottage Near Dovedale

Bankside Cottage, Milldale – Cosy Peak District Holiday Cottage Near Dovedale
Alstonfield
9.8 out of 10, Exceptional, (16 reviews)
"We had a lovely time staying in Bankside cottage. Well appointed cottage with all you need for a stay in the Peak District. Perfectly situated for walks along the river and cycling on the Tissington Trail."
United Kingdom
Tom G.
Bankside Cottage, Milldale – Cosy Peak District Holiday Cottage Near Dovedale

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

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.

Eco 2-Bed Bungalow with Biodiverse Garden & Solar

Eco 2-Bed Bungalow with Biodiverse Garden & Solar
Bestwood Village
10.0 out of 10, Exceptional, (3 reviews)
"Rob and Jill were brilliant. We’ll definitely stay there again next time we visit Linby. "
Australia
Warren Z.
Eco 2-Bed Bungalow with Biodiverse Garden & Solar

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 £91
includes taxes & fees
30 Apr - 1 May
2bed - garden-pets-freeparking-M1connections

Cosy Cottage in the Beautiful Derbyshire Dales, Peak District

Cosy Cottage in the Beautiful Derbyshire Dales, Peak District
Winster
9.4 out of 10, Exceptional, (16 reviews)
"The cottage was just as pictured in a lovely location not far from Haddon Hall, Matlock and Buxton. Andrew ideal place to stay and explore the Peak District."
United Kingdom
Andrew D.
Cosy Cottage in the Beautiful Derbyshire Dales, Peak District

Dryden House

Dryden House
3.5 star property
Chesterfield
Dryden House

Southdown House

Southdown House
3.0 star property
Chesterfield
Southdown House
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 648 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 £91 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
419
Accommodation
648 Holiday Homes
Lowest Price
£91
Highest Price
£151

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