A stone path winding through a valley with a sunset in the background.

Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Chesterfield vacation rentals

Property grounds

1. The Old School House

The Old School House
Brimington
The price is ￥31,937
￥36,529 total
includes taxes & fees
Oct 17 - Oct 18
The Old School House
A conservatory with a dining table set for six, surrounded by large windows offering a view of a garden.

2. Cherry Tree Farm

Cherry Tree Farm
3.0 star property
Chesterfield
The price is ￥283,179
￥339,815 total
includes taxes & fees
Nov 15 - Nov 16
Cherry Tree Farm
A wooden deck with two wicker sofas and a table, surrounded by a white lattice fence.

3. 2 bedroom accommodation in Holymoorside

2 bedroom accommodation in Holymoorside
Holymoorside
10.0 out of 10, Exceptional, (5 reviews)
"Really enjoyed this place, lovely and clean, comfy quiet and beautiful scenery."
United States
V & P Roberts
The price is ￥57,821
￥57,821 total
includes taxes & fees
Oct 31 - Nov 1
2 bedroom accommodation in Holymoorside
A dining area with a wooden table and chairs, a stone wall, and a view of the garden through a glass door.

4. Bathurst Cottage is a delightful three bedroom detached cottage.

Bathurst Cottage is a delightful three bedroom detached cottage.
Chesterfield
10.0 out of 10, Exceptional, (2 reviews)
"Spotless, well looked after cottage. Very homely and cosy.Well equipped kitchen.Lovely hosts, great welcome hamper with lovely treats."
United States
Valerie Thompson
The price is ￥55,734
￥55,734 total
includes taxes & fees
Nov 1 - Nov 2
Bathurst Cottage is a delightful three bedroom detached cottage.
A cozy living room with a fireplace, comfortable seating, and a large window with curtains.

5. Bryn Tor - The Gardener's House

Bryn Tor - The Gardener's House
Bolsover, near Chesterfield
The price is ￥115,497
￥115,497 total
includes taxes & fees
Oct 21 - Oct 22
Bryn Tor - The Gardener's House
A natural landscape with a stream, trees, and a grassy area.

6. Little Mill

Little Mill
2.0 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 ￥58,020
￥69,624 total
includes taxes & fees
Oct 23 - Oct 24
Little Mill
A living room with a brown leather sofa, a wooden cabinet, a television, and a radiator.

7. Carr House Farm

Carr House Farm
2.0 star property
Chesterfield
The price is ￥77,360
￥92,832 total
includes taxes & fees
Oct 21 - Oct 22
Carr House Farm
A hot tub under a wooden pergola with a stone wall and greenery in the background.

8. Cherry Tree Cottage

Cherry Tree Cottage
3.0 star property
Chesterfield
10.0 out of 10, Exceptional, (2 reviews)
"The property was lovely and clean beautiful views and was so relaxing"
United Kingdom
Lorraine
The price is ￥113,555
￥136,266 total
includes taxes & fees
Oct 24 - Oct 25
Cherry Tree Cottage
A sunlit room with a large window, a sofa, a table, and a potted plant.

9. Overton

Overton
2.0 star property
Chesterfield
Overton
A bedroom with a bed, a nightstand, a chair, a window with curtains, and a door.

10. Cedar Cottage

Cedar Cottage
3.5 star property
Chesterfield
The price is ￥68,843
￥82,612 total
includes taxes & fees
Oct 19 - Oct 20
Cedar Cottage
A stone building with a pitched roof, a small porch, and a stone wall in the background.

11. Riber View Barn

Riber View Barn
3.0 star property
Chesterfield
The price is ￥60,859
￥73,031 total
includes taxes & fees
Nov 2 - Nov 3
Riber View Barn
A cozy cabin-style interior with a kitchen, dining area, and seating space.

12. Thorntree Lodge

Thorntree Lodge
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (1 review)
The price is ￥83,570
￥100,284 total
includes taxes & fees
Oct 23 - Oct 24
Thorntree Lodge
A bedroom with a bed, a television, a nightstand, and a bathroom visible through a doorway.

13. The Old Stables

The Old Stables
3.5 star property
Chesterfield
The price is ￥126,863
￥152,236 total
includes taxes & fees
Oct 19 - Oct 20
The Old Stables
A modern kitchen with white cabinets, a wooden countertop, and a built-in sink. There is a wooden ladder leaning against the wall and a sliding glass door leading to an outdoor deck.

14. Cuckoo Nest

Cuckoo Nest
3.5 star property
Chesterfield
The price is ￥58,020
￥69,624 total
includes taxes & fees
Oct 19 - Oct 20
Cuckoo Nest
A wooden deck with outdoor seating and a glass door leading to a covered area.

15. Harry's Lodge

Harry's Lodge
3.0 star property
Chesterfield
The price is ￥89,602
￥107,522 total
includes taxes & fees
Oct 22 - Oct 23
Harry's Lodge
A cozy room with a wooden ceiling, a sofa, and a window with curtains.

16. Swallows Barn

Swallows Barn
3.5 star property
Chesterfield
The price is ￥106,458
￥127,750 total
includes taxes & fees
Nov 6 - Nov 7
Swallows Barn
A living room with a stone wall, a fireplace, leather sofas, and a television.

17. The Cottage

The Cottage
3.0 star property
Chesterfield
The price is ￥109,297
￥131,156 total
includes taxes & fees
Nov 13 - Nov 14
The Cottage
A hot tub in a backyard with a stone wall and a grassy lawn.

18. Wigley Farm House Cottage

Wigley Farm House Cottage
3.0 star property
Chesterfield
6.0 out of 10, (1 review)
"I'll start with the good. Location is nice and peaceful. The bungalow is well laid out and there is plenty of room. Facilities inside the bungalow are good. Cooking and dining implements all there and lots of space. Bedrooms are nice and have plenty of storage for a short break. The garden is well maintained and enclosed although there is only 2 comfortable chairs and no swing or sofa. Parking around the back of the property is the best but you are encouraged to park at the front tucked...
United Kingdom
June
The price is ￥107,523
￥129,028 total
includes taxes & fees
Oct 19 - Oct 20
Wigley Farm House Cottage
An outdoor dining area with wicker chairs, a glass table, and a hot tub in the background.

19. Moor Farm Cottage

Moor Farm Cottage
3.0 star property
Chesterfield
The price is ￥108,765
￥130,518 total
includes taxes & fees
Oct 21 - Oct 22
Moor Farm Cottage
A stone building with a sign reading "The George Country Pub & Dining."

20. The Loft at The George

The Loft at The George
3.5 star property
Chesterfield
The price is ￥97,942
￥117,530 total
includes taxes & fees
Oct 19 - Oct 20
The Loft at The George
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 Hotel Reviews

Ringwood Hall Hotel & Spa, BW Signature Collection

Ringwood Hall Hotel & Spa, BW Signature Collection

10/10 Excellent
"The staff were really helpful and friendly and catered for my uncles dog. They have a lot of appliances in the room allowing a comfortable stay. Here is also a nice park near bye if you find the grounds not big enough to wonder. Overall great trip away with amazing scenery."
anton 2-night trip
Posted 1 hour ago
Ringwood Hall Hotel & Spa, BW Signature Collection

Find out more about Chesterfield

Search for holiday rentals in Chesterfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesterfield using one of the methods below:

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Look no further and take a look at our great range of rental properties in Chesterfield!

Frequently asked questions

Can I find a vacation rental in Chesterfield?

Yes, you can find vacation rentals in Chesterfield close to Clay Cross Active, or you can choose a secluded option if you want a relaxing stay. Our travelers say Chesterfield has a good selection of top-notch restaurants and lively bars. Make sure you have time to check out the churches and parks during your trip.

What are some of the best vacation home rentals that Chesterfield has to offer?

Old Nags Head: You might want to consider this vacation home rental near Chesterfield, which comes with free WiFi so you can feel at home during your trip. Kitchen amenities include a stovetop, a microwave, and kitchenware.

How many vacation rentals will I find in Chesterfield?

With 43 Expedia vacation rentals, you're sure to find just the right place for your Chesterfield stay.

What can I see and do in Chesterfield?

Enjoy the outdoors at Peak District National Park and Queen's Park, or simply take in cultural attractions like Barrow Hill Roundhouse Railway Centre and Hotel Van Dyk Theater. Chesterfield Market and Bolsover Castle are other places to visit while you're in town.

What are vacation rentals like in Chesterfield?

Vacation rentals are private properties you can stay in for several days or longer in Chesterfield. Vacation rentals feature extras such as WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for a family trip or a small group gathering.