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
$1,917 nightly
The price is $2,300
Oct 13 - Oct 14
Total with taxes and fees
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
$392 nightly
The price is $392
Oct 9 - Oct 10
Total with taxes and fees
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
$378 nightly
The price is $378
Nov 1 - Nov 2
Total with taxes and fees
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
$733 nightly
The price is $733
Oct 21 - Oct 22
Total with taxes and fees
Bryn Tor - The Gardener's House
A stone building with two wooden doors and a small window.

5. Carr House Farm

Carr House Farm
2.0 star property
Chesterfield
$491 nightly
The price is $589
Oct 10 - Oct 11
Total with taxes and fees
Carr House Farm
A stone building with a sloped roof, wooden doors, and a gravel driveway.

6. Little Mill

Little Mill
2.0 star property
Chesterfield
$368 nightly
The price is $442
Oct 7 - Oct 8
Total with taxes and fees
Little Mill
A wooden cabin with a fenced backyard, a small porch, and a stone wall in the background.

7. Thorntree Lodge

Thorntree Lodge
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (1 review)
$530 nightly
The price is $636
Oct 14 - Oct 15
Total with taxes and fees
Thorntree Lodge
A bathroom with a freestanding bathtub, a wooden vanity with drawers, a toilet, and a mirror.

8. The Old Stables

The Old Stables
3.5 star property
Chesterfield
$805 nightly
The price is $966
Oct 7 - Oct 8
Total with taxes and fees
The Old Stables
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
$720 nightly
The price is $864
Oct 10 - Oct 11
Total with taxes and fees
Cherry Tree Cottage
A brick house with a white door, a small garden, and a patio with a table and chairs.

10. Cedar Cottage

Cedar Cottage
3.5 star property
Chesterfield
$437 nightly
The price is $524
Oct 9 - Oct 10
Total with taxes and fees
Cedar Cottage
A wooden deck with a wicker sofa and a round table, overlooking a green landscape.

11. Cuckoo Nest

Cuckoo Nest
3.5 star property
Chesterfield
$368 nightly
The price is $442
Oct 7 - Oct 8
Total with taxes and fees
Cuckoo Nest
A rustic lodge with a sign reading "Harry's Lodge," surrounded by lush greenery and a stone wall.

12. Harry's Lodge

Harry's Lodge
3.0 star property
Chesterfield
$568 nightly
The price is $682
Oct 10 - Oct 11
Total with taxes and fees
Harry's Lodge
A backyard with a small lawn, a wooden shed, and a tall bamboo fence.

13. Overton

Overton
2.0 star property
Chesterfield
$634 nightly
The price is $760
Oct 9 - Oct 10
Total with taxes and fees
Overton
A stone house with a large glass bay window, a patio with outdoor furniture, and a well-maintained lawn.

14. Swallows Barn

Swallows Barn
3.5 star property
Chesterfield
$675 nightly
The price is $810
Oct 9 - Oct 10
Total with taxes and fees
Swallows Barn
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
$386 nightly
The price is $463
Oct 16 - Oct 17
Total with taxes and fees
Riber View Barn
Interior

16. The Loft

The Loft
3.5 star property
Chesterfield
$669 nightly
The price is $802
Oct 7 - Oct 8
Total with taxes and fees
The Loft
A stone building with a gravel driveway and two potted plants.

17. The Cottage

The Cottage
3.0 star property
Chesterfield
$693 nightly
The price is $832
Oct 9 - Oct 10
Total with taxes and fees
The Cottage
A stone building with a large window, a stone archway, and a garden with hedges and a flower bed.

18. The Tack Room Cottage

The Tack Room Cottage
3.0 star property
Chesterfield
$625 nightly
The price is $750
Oct 7 - Oct 8
Total with taxes and fees
The Tack Room Cottage
A stone building with two arched windows, a small door, and a garden with various plants.

19. 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
$502 nightly
The price is $502
Oct 17 - Oct 18
Total with taxes and fees
The Old Chapel
An outdoor dining area with wicker chairs, a glass table, and a hot tub in the background.

20. Moor Farm Cottage

Moor Farm Cottage
3.0 star property
Chesterfield
$690 nightly
The price is $828
Oct 9 - Oct 10
Total with taxes and fees
Moor Farm 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

The Orchard Hotel & Restaurant

The Orchard Hotel & Restaurant

8/10 Good
"Great atmosphere and excellent and clean room. Beds only double but adequate. Good breakfast and relaxed environment. Bar staff specially Coco was most cortiouse and polite bar tender ever with exceptional knowledge. Only issue we had was had confusing information or lack of it before checking."
Nima 1-night trip
Posted 5 hours ago
The Orchard Hotel & Restaurant

Find out more about Chesterfield

Chesterfield Cottages information

Number of reviews
11
Accommodation
2043 Cottages
Lowest Price
$378
Highest Price
$2,300

Frequently asked questions

How much do cottages in Chesterfield cost?
Cottages in Chesterfield range between $378 and $2,300 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 favorite 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 10.0.
How many cottages are there in Chesterfield?
Take your pick of 2043 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 $378 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 favorites. 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?
Traveling 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 travelers 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.

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