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

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Chesterfield cottages

An outdoor patio with a table, chairs, a hot tub, and a view of a golf course.

1. Cherry Tree Farm

Cherry Tree Farm
3.0 star property
Chesterfield
The price is CA $2,733
CA $3,279 total
includes taxes & fees
Oct 13 - Oct 14
Cherry Tree Farm
A vintage blue car parked in front of a white house with a green door and a sign that reads "Oatlands."

2. 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 CA $556
CA $556 total
includes taxes & fees
Oct 9 - Oct 10
2 bedroom accommodation in Holymoorside
A white stone building with a large tree in front, a picnic table, and a stone wall.

3. 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 CA $536
CA $536 total
includes taxes & fees
Nov 1 - Nov 2
Bathurst Cottage is a delightful three bedroom detached cottage.
A balcony with a view of a field, a table with chairs, and a potted plant.

4. Bryn Tor - The Gardener's House

Bryn Tor - The Gardener's House
Bolsover, near Chesterfield
The price is CA $1,038
CA $1,038 total
includes taxes & fees
Nov 1 - Nov 2
Bryn Tor - The Gardener's House
A backyard with a small lawn, a wooden shed, and a tall bamboo fence.

5. Overton

Overton
2.0 star property
Chesterfield
The price is CA $898
CA $1,078 total
includes taxes & fees
Oct 14 - Oct 15
Overton
A stone building with two wooden doors and a small window.

6. Carr House Farm

Carr House Farm
2.0 star property
Chesterfield
The price is CA $696
CA $835 total
includes taxes & fees
Nov 2 - Nov 3
Carr House Farm
A brick house with a white door, a small garden, and a patio with a table and chairs.

7. Cedar Cottage

Cedar Cottage
3.5 star property
Chesterfield
The price is CA $619
CA $743 total
includes taxes & fees
Oct 14 - Oct 15
Cedar Cottage
A stone building with a sloped roof, wooden doors, and a gravel driveway.

8. Little Mill

Little Mill
2.0 star property
Chesterfield
The price is CA $522
CA $626 total
includes taxes & fees
Oct 16 - Oct 17
Little Mill
A hot tub under a wooden pergola with a stone wall and greenery in the background.

9. 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 CA $1,021
CA $1,225 total
includes taxes & fees
Oct 24 - Oct 25
Cherry Tree Cottage
A wooden deck with a wicker sofa and a round table, overlooking a green landscape.

10. Cuckoo Nest

Cuckoo Nest
3.5 star property
Chesterfield
The price is CA $522
CA $626 total
includes taxes & fees
Oct 7 - Oct 8
Cuckoo Nest
A stone building with a gravel driveway and two potted plants.

11. The Cottage

The Cottage
3.0 star property
Chesterfield
The price is CA $983
CA $1,179 total
includes taxes & fees
Oct 9 - Oct 10
The Cottage
A stone house with a large glass bay window, a patio with outdoor furniture, and a well-maintained lawn.

12. Swallows Barn

Swallows Barn
3.5 star property
Chesterfield
The price is CA $957
CA $1,149 total
includes taxes & fees
Oct 9 - Oct 10
Swallows Barn
An outdoor dining area with wicker chairs, a glass table, and a hot tub in the background.

13. Moor Farm Cottage

Moor Farm Cottage
3.0 star property
Chesterfield
The price is CA $978
CA $1,174 total
includes taxes & fees
Oct 9 - Oct 10
Moor Farm Cottage
A rustic lodge with a sign reading "Harry's Lodge," surrounded by lush greenery and a stone wall.

14. Harry's Lodge

Harry's Lodge
3.0 star property
Chesterfield
The price is CA $806
CA $967 total
includes taxes & fees
Oct 11 - Oct 12
Harry's Lodge
A stone building with a pitched roof, a small porch, and a stone wall in the background.

15. Riber View Barn

Riber View Barn
3.0 star property
Chesterfield
The price is CA $547
CA $657 total
includes taxes & fees
Oct 16 - Oct 17
Riber View Barn
A stone house with a well-maintained garden, a stone wall, and a clear sky.

16. 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 CA $967
CA $1,160 total
includes taxes & fees
Oct 6 - Oct 7
Wigley Farm House Cottage
A stone building with two arched windows, a small door, and a garden with various plants.

17. The Old Chapel

The Old Chapel
3.0 star property
Chesterfield
10.0 out of 10, Exceptional, (2 reviews)
"Out in the country but easy access to main routes. Nice and quiet. Very clean and well equipped. Nice owners. "
United Kingdom
Mark
The price is CA $716
CA $716 total
includes taxes & fees
Oct 17 - Oct 18
The Old Chapel
A stone building with multiple windows, a door, and a signboard.

18. The Loft at The George

The Loft at The George
3.5 star property
Chesterfield
The price is CA $881
CA $1,057 total
includes taxes & fees
Nov 1 - Nov 2
The Loft at The George
A stone house with a sloped roof, a green door, and a mailbox attached to the wall.

19. Woodthorpe Cruck Cottage

Woodthorpe Cruck Cottage
3.5 star property
Chesterfield
9.0 out of 10, Wonderful, (2 reviews)
"Amazing cottage in amazing location.will definetly be back"
United Kingdom
Anthony
The price is CA $976
CA $1,172 total
includes taxes & fees
Oct 11 - Oct 12
Woodthorpe Cruck Cottage
A stone building with a large window, a stone archway, and a garden with hedges and a flower bed.

20. The Tack Room Cottage

The Tack Room Cottage
3.0 star property
Chesterfield
The price is CA $885
CA $1,063 total
includes taxes & fees
Oct 31 - Nov 1
The Tack Room Cottage
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

WILDES INNS

WILDES INNS

8/10 Good
"Overall it was a good experience: staff, value, ambience and food. Some elements were disappointing - toothpaste on a clean(?) towel, blood specks on a pillow. And I had requested a quiet room which was acknowledged prior to my visit. I was given a room over the bar courtyard - music played under my window until I requested it was switched off at 9pm up to which time no one had used the courtyard due to the cool weather. Thankfully it wasn't in the heat of summer. And sadly the modern hotel construction meant the room above picked up all noise from movements. I didn't think that a bit of extra thought would have put me in a room that would have offered a more quiet environment which it clearly wasn't, showing either wilful disregard for my request or no thought it through. Did I complain? Did I need to. The damage had been done."
Simon 2-night trip
Posted 8 hours ago
WILDES INNS

Find out more about Chesterfield

Chesterfield Cottages information

Number of reviews
14
Accommodation
1695 Cottages
Lowest Price
CA $556
Highest Price
CA $3,279

Frequently asked questions

How much do cottages in Chesterfield cost?
Cottages in Chesterfield range between CA $556 and CA $3,279 per night. These properties offer a chance to soak up nature's beauty — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best cottages in Chesterfield?
A guest favourite is Thorntree Lodge. Cozy up at this 3.5-star stay which features a garden and individually decorated rooms. Shire Cottage At Top Butterley Farm is another popular option worth shortlisting. Unpack your bags at this 3-star cottage and take advantage of conveniences including individually decorated rooms and WiFi. You can choose from multiple cottages in Chesterfield with a total average guest review rating of 9.2.
How many cottages are there in Chesterfield?
Take your pick of 1695 cottages in Chesterfield. Whether you're traveling with the kids or organizing a weekend escape with your closest amigos, Expedia can help you find the perfect property to get back to nature.
What are the best cheap cottages in Chesterfield?
With cottages starting at just CA $556 per night, you may want to extend your trip to Chesterfield! One retreat that's easy on your budget is The Rumblings 1. It offers useful amenities like individually decorated rooms and WiFi. Another inexpensive pick where you can enjoy a break from the routine is The Rumblings 2. Individually decorated rooms and WiFi are among the conveniences here. If you're exploring Chesterfield on a budget, there are loads of terrific free attractions to put on your itinerary. Chesterfield Museum & Art Gallery and Chesterfield Market are always favourites. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Are there any family-friendly cottages in Chesterfield?
Travelling with your group in Chesterfield is a breeze at Thorntree Lodge. With conveniences including a fireplace and WiFi, you can rest and relax at this 3.5-star cottage. Shire Cottage At Top Butterley Farm is another family-friendly stay where you and the rest of the squad can take time out from the relentless pace of the big city. This cottage has a 3-star rating and conveniences including WiFi and a stovetop. Chesterfield boasts an array of family-friendly attractions to visit when the kids are getting restless. Bolsover Castle and Barrow Hill Roundhouse Railway Centre promise a fun day out for travellers young and old.
Why book your cottage in Chesterfield with Expedia?
Reserving a cottage in Chesterfield is as easy as clicking on your travel dates and selecting an ideal place for outdoor relaxation and recreation. From luxurious retreats to low-cost stays and cottages that come with perks like a hot tub, Expedia has something for all tastes and styles. As for unbeatable deals? We have them too!
How can I find cheap cottages in Chesterfield?
A wonderful way to score cheap cottages in Chesterfield is with Expedia's convenient filter tool. Narrow your search results by amenities, star rating and budget to land unbeatable deals in just a few keystrokes.
What is there to do in Chesterfield near my cottage?
Chesterfield has enough activities and experiences to keep you busy for weeks, beginning with Chesterfield Market. Bolsover Castle, Hardwick Hall and Hotel Van Dyk Theater are other renowned attractions. If you're lingering longer, Hardwick Hall-Derbyshire Country Park and Poolsbrook Country Park will add the finishing touches to your itinerary.