A sign indicating visitor mooring with a 2-day limit, a canal, and a grassy bank with trees in the background.

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Chesterfield cottages

1. LITTLE MILL, pet friendly, character holiday cottage in Ashover

LITTLE MILL, pet friendly, character holiday cottage in Ashover
2.0 star property
Chesterfield
$443 nightly
The price is $443
Sep 3 - Sep 4
Total with taxes and fees
LITTLE MILL, pet friendly, character holiday cottage in Ashover
A stone building with two wooden doors and a small window.

2. Carr House Farm

Carr House Farm
2.0 star property
Chesterfield
$502 nightly
The price is $602
Sep 16 - Sep 17
Total with taxes and fees
Carr House Farm
A vintage blue car parked in front of a white house with a green door and a sign that reads "Oatlands."

3. 2 bedroom accommodation in Holymoorside

2 bedroom accommodation in Holymoorside
Holymoorside
10.0 out of 10, Exceptional, (4 reviews)
"Really enjoyed this place, lovely and clean, comfy quiet and beautiful scenery."
United States
V & P Roberts
$375 nightly
The price is $375
Sep 18 - Sep 19
Total with taxes and fees
2 bedroom accommodation in Holymoorside
A gated entrance to a house with a garden, a paved pathway, and a clear sky.

4. Bryn Tor - The Gardener's House

Bryn Tor - The Gardener's House
Bolsover, near Chesterfield
$749 nightly
The price is $749
Sep 3 - Sep 4
Total with taxes and fees
Bryn Tor - The Gardener's House
An outdoor patio with a table, chairs, a hot tub, and a view of a golf course.

5. Cherry Tree Farm

Cherry Tree Farm
3.0 star property
Chesterfield
$1,823 nightly
The price is $2,188
Sep 22 - Sep 23
Total with taxes and fees
Cherry Tree Farm

6. Little Mill

Little Mill
2.0 star property
Chesterfield
$376 nightly
The price is $452
Sep 22 - Sep 23
Total with taxes and fees
Little Mill
A backyard with a small lawn, a wooden shed, and a tall bamboo fence.

7. Overton

Overton
2.0 star property
Chesterfield
$648 nightly
The price is $777
Sep 6 - Sep 7
Total with taxes and fees
Overton
A brick house with a white door, a small garden, and a patio with a table and chairs.

8. Cedar Cottage

Cedar Cottage
3.5 star property
Chesterfield
$446 nightly
The price is $536
Sep 16 - Sep 17
Total with taxes and fees
Cedar Cottage
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
$736 nightly
The price is $884
Sep 29 - Sep 30
Total with taxes and fees
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
$376 nightly
The price is $452
Sep 9 - Sep 10
Total with taxes and fees
Cuckoo Nest
A stone house with a well-maintained garden, a stone wall, and a clear sky.

11. Wigley Farm House Cottage

Wigley Farm House Cottage
3.0 star property
Chesterfield
$697 nightly
The price is $837
Sep 29 - Sep 30
Total with taxes and fees
Wigley Farm House Cottage
An outdoor dining area with wicker chairs, a glass table, and a hot tub in the background.

12. Moor Farm Cottage

Moor Farm Cottage
3.0 star property
Chesterfield
$705 nightly
The price is $846
Sep 6 - Sep 7
Total with taxes and fees
Moor Farm Cottage
A stone building with two arched windows, a small door, and a garden with various plants.

13. 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
$514 nightly
The price is $514
Sep 29 - Sep 30
Total with taxes and fees
The Old Chapel
A stone building with a pitched roof, a small porch, and a stone wall in the background.

14. Riber View Barn

Riber View Barn
3.0 star property
Chesterfield
$395 nightly
The price is $474
Sep 26 - Sep 27
Total with taxes and fees
Riber View Barn
A stone building with a gravel driveway and two potted plants.

15. The Cottage

The Cottage
3.0 star property
Chesterfield
$710 nightly
The price is $853
Oct 2 - Oct 3
Total with taxes and fees
The Cottage
A stone building with multiple windows, a door, and a signboard.

16. The Loft at The George

The Loft at The George
3.5 star property
Chesterfield
$635 nightly
The price is $762
Sep 6 - Sep 7
Total with taxes and fees
The Loft at The George
A stone house with a sloped roof, a green door, and a mailbox attached to the wall.

17. 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
$691 nightly
The price is $829
Sep 24 - Sep 25
Total with taxes and fees
Woodthorpe Cruck 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
$639 nightly
The price is $767
Sep 27 - Sep 28
Total with taxes and fees
The Tack Room Cottage
A bathroom with a freestanding bathtub, a wooden vanity with drawers, a toilet, and a mirror.

19. The Old Stables

The Old Stables
3.5 star property
Chesterfield
$823 nightly
The price is $987
Sep 6 - Sep 7
Total with taxes and fees
The Old Stables
A wooden cabin with a fenced backyard, a small porch, and a stone wall in the background.

20. Thorntree Lodge

Thorntree Lodge
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (1 review)
$542 nightly
The price is $650
Sep 26 - Sep 27
Total with taxes and fees
Thorntree Lodge
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

Leonardo Hotel Sheffield

Leonardo Hotel Sheffield

10/10 Excellent
"Hotel is very nice. Rooms are comfortable and well maintained. Restaurant served good food and the staff were welcoming and helpful. Reception staff were very helpful. Parking was a pain if you don’t know the area. Mentions where it is up the road but would be helpful if they mention it’s called Moor car park on the site."
James 1-night trip
Posted less than an hour ago
Leonardo Hotel Sheffield

Find out more about Chesterfield

Chesterfield Cottages information

Number of reviews
10
Accommodation
2043 Cottages
Lowest Price
$375
Highest Price
$2,188

Frequently asked questions

How much do cottages in Chesterfield cost?
Cottages in Chesterfield range between $375 and $2,188 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 9.8.
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 $375 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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