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Holiday Rentals in Chesterfield District

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Top cities in Chesterfield District

Railway tracks surrounded by greenery and trees.
Vacation Rentals

Staveley

Staveley

Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Chesterfield District holiday rentals

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

1. The Old School House

The Old School House
Brimington
The price is €203
includes taxes & fees
12 Nov - 13 Nov
The Old School House
A sunlit room with a large window, a sofa, a table, and a potted plant.

2. Overton

Overton
3.0 star property
Chesterfield
The price is €756
includes taxes & fees
16 Nov - 17 Nov
Overton
A bedroom with a bed, a nightstand, a chair, a window with curtains, and a door.

3. Cedar Cottage

Cedar Cottage
3.5 star property
Chesterfield
The price is €521
includes taxes & fees
15 Nov - 16 Nov
Cedar Cottage
A modern loft bedroom with a sloped ceiling, a black leather sofa, a wooden chair, and a TV stand.

4. Relaxing En-Suite Apartment with Private Lounge, Kitchen and Parking

Relaxing En-Suite Apartment with Private Lounge, Kitchen and Parking
Nether Edge
10.0 out of 10, Exceptional, (2 reviews)
"Perfect"
United Kingdom
Adam
The price is €99
includes taxes & fees
8 Nov - 9 Nov
Relaxing En-Suite Apartment with Private Lounge, Kitchen and Parking
A building with a stone facade, a balcony with outdoor seating, and a clear sky.

5. Rock Mill Retreat

Rock Mill Retreat
Stoney Middleton
10.0 out of 10, Exceptional, (2 reviews)
"For me - everything was comfortable😃 Beautiful interior, red-light,and after walking on the local hills, really comfortable sleeping in the unic-bed!"
Italy
Gabriela
The price is €202
includes taxes & fees
10 Nov - 11 Nov
Rock Mill Retreat
A dining area with a table set for four, a large window with a view of a red brick building, and a painting of a coastal landscape.

6. North Gate House

North Gate House
2.0 star property
Sheffield City Centre
The price is €113
includes taxes & fees
8 Nov - 9 Nov
North Gate House
A modern restaurant interior with large windows, tables, and chairs.

7. Sheffield Metropolitan by Belvilla - Standard Double Room

Sheffield Metropolitan by Belvilla - Standard Double Room
Sheffield
9.6 out of 10, Exceptional, (60 reviews)
"Absolutely fantastic stay. Amazing value and perfect location. The staff were incredibly friendly and welcoming. The breakfast was freshly cooked and simply excellent."
United States
Anonymous traveller
The price is €45
includes taxes & fees
22 Nov - 23 Nov
Sheffield Metropolitan by Belvilla - Standard Double Room
A stone building with a water wheel and a staircase.

8. Little Mill

Little Mill
3.0 star property
Chesterfield
10.0 out of 10, Exceptional, (1 review)
"Lovely little cottage in a beautiful setting. Great walks around. Bed comfortable and lovely warm shower. The welcome package was very helpful as I arrived late on Sunday and forgot the English shops closed early!"
United Kingdom
Rona
The price is €439
includes taxes & fees
14 Nov - 15 Nov
Little Mill
A living room with a sofa, a coffee table with croissants, a TV, and a staircase.

9. Gratton Grange Farm Holiday Cottage

Gratton Grange Farm Holiday Cottage
3.0 star property
Bakewell
9.2 out of 10, Wonderful, (65 reviews)
"Lovely house and very quiet location which is what I loved . Everything you needed in terms of kitchen facilities /utensils etc . Lovely comfy bed , down side was late check in 4pm and early check out out 10am , no breakfast included but other than than lovely ."
United Kingdom
Irene
The price is €162
includes taxes & fees
8 Nov - 9 Nov
Gratton Grange Farm Holiday Cottage
A hotel room with a bed, a window with curtains, a radiator, and a door leading to a bathroom.

10. Kingfield Boutique Hotel

Kingfield Boutique Hotel
3.5 star property
Nether Edge
5.8 out of 10, (10 reviews)
"Great value accommodation "
United Kingdom
Caroline
The price is €85
includes taxes & fees
9 Nov - 10 Nov
Kingfield Boutique Hotel
A dining area with a table set for two, a vase of yellow flowers, and a view of a green landscape through a window.

11. Oak Tree Shepherd's Hut Chatsworth Estate

Oak Tree Shepherd's Hut Chatsworth Estate
Baslow
10.0 out of 10, Exceptional, (1 review)
"Stunning location - perfect for anyone wishing to escape the hustle & bustle of life. "
United Kingdom
Teresa
The price is €197
includes taxes & fees
8 Nov - 9 Nov
Oak Tree Shepherd's Hut Chatsworth Estate
A cozy room with a dark blue sofa, a wooden wall with a 'NEWSPAPER' sign, a small wooden cabinet, and a window with a view of the outside.

12. Houseboat Hotels

Houseboat Hotels
3.0 star property
Sheffield
9.4 out of 10, Exceptional, (61 reviews)
"Another excellent trip on the houseboat. Love this hotel - great location, fabulous accommodation. Why stay in a regular hotel when you can stay here!"
United Kingdom
Wendy
The price is €174
includes taxes & fees
22 Nov - 23 Nov
Houseboat Hotels
A compact kitchen with a microwave, sink, and dark cabinets. There's a wooden door leading to another room and a sofa in the corner.

13. Meadow View - (Bottom Cabin) - sleeps 2 guests in 1 bedroom

Meadow View - (Bottom Cabin) - sleeps 2 guests in 1 bedroom
Foolow
10.0 out of 10, Exceptional, (5 reviews)
"Enjoyable stay"
United Kingdom
Michael
The price is €138
includes taxes & fees
9 Nov - 10 Nov
Meadow View - (Bottom Cabin) - sleeps 2 guests in 1 bedroom
A cozy room with a bed, a sofa, a desk, and a window with curtains.

14. Hare’s Retreat - ( Middle Cabin ) - sleeps 2 guests in 1 bedroom

Hare’s Retreat - ( Middle Cabin ) - sleeps 2 guests in 1 bedroom
Foolow
10.0 out of 10, Exceptional, (1 review)
"Clean and a nice place to stay. This was our second visit to the cabins with our dog and Penny was very helpful."
United Kingdom
Michael
The price is €139
includes taxes & fees
9 Nov - 10 Nov
Hare’s Retreat - ( Middle Cabin ) - sleeps 2 guests in 1 bedroom
Restaurant

15. Old Nags Head

Old Nags Head
3.0 star property
Hope Valley
10.0 out of 10, Exceptional, (4 reviews)
"Perfect location. Warm staff. Great room."
United Kingdom
Kai
The price is €170
includes taxes & fees
18 Nov - 19 Nov
Old Nags Head
A room with exposed wooden beams, a flat-screen TV mounted on the wall, and three hanging light bulbs.

16. Three Cranes Serviced Apartments

Three Cranes Serviced Apartments
3.5 star property
Sheffield City Centre
8.4 out of 10, Very good, (133 reviews)
"Great place to stay"
United Kingdom
Graham
The price is €80
includes taxes & fees
10 Nov - 11 Nov
Three Cranes Serviced Apartments
A modern living room with a grey sofa, a round coffee table, and a dining table with chairs. There are two windows with blinds, a mirror on the wall, and a door leading to another room.

17. 3 BR Bungalow close to Peak District with Garden

3 BR Bungalow close to Peak District with Garden
South Yorkshire
9.2 out of 10, Wonderful, (5 reviews)
"We loved our stay in this beautiful, accessible home. It was a great location and the host was very helpful. "
United States
Meghan D.
The price is €285
includes taxes & fees
11 Nov - 12 Nov
3 BR Bungalow close to Peak District with Garden
A hot tub under a wooden pergola with a stone wall and greenery in the background.

18. Cherry Tree Cottage

Cherry Tree Cottage
3.0 star property
Chesterfield
10.0 out of 10, Exceptional, (3 reviews)
"The property was lovely and clean beautiful views and was so relaxing"
United Kingdom
Lorraine
The price is €782
includes taxes & fees
22 Nov - 23 Nov
Cherry Tree Cottage
A modern kitchen with built-in appliances, a dining area with a wooden table and chairs, and a clock on the wall.

19. Brewers Cottage - sleeps 2 guests in 1 bedroom

Brewers Cottage - sleeps 2 guests in 1 bedroom
Foolow
10.0 out of 10, Exceptional, (7 reviews)
"Ideal for us on a short visit to family with fog in tow. Foolow a lovely village with great pub and stunning views"
United States
marcus s.
The price is €172
includes taxes & fees
9 Nov - 10 Nov
Brewers Cottage - sleeps 2 guests in 1 bedroom
A dining table set with plates, cutlery, and a fruit bowl, surrounded by colorful chairs.

20. Spacesavers

Spacesavers
3.5 star property
Sheffield City Centre
8.2 out of 10, Very good, (59 reviews)
"Great location "
United Kingdom
Lynsey
The price is €80
includes taxes & fees
10 Nov - 11 Nov
Spacesavers
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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Find holiday rentals that suit your style

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Top Chesterfield District Hotel Reviews

A bed with a headboard, two bedside tables, and pillows.
Bridleways Guest House & Holiday Homes

Bridleways Guest House & Holiday Homes

Bridleways Guest House & Holiday Homes
Mansfield

10/10 Excellent

Lovely guest house in a beautiful setting. Staff were friendly, helpful and attentive. Food was great. Rooms were spotless and warm
Ireland
James
Reviewed November 2, 2025
Bridleways Guest House & Holiday Homes

Find out more about Chesterfield District

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

Chesterfield District holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesterfield District. 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 District 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 District holiday rentals we have selected for you start as low as €44 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chesterfield District rentals

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