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

Search Cottages in Chesterfield

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Our top choices for Chesterfield cottages

A vintage blue car parked in front of a white house with a green door and a sign that reads "Oatlands."

1. 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
2 bedroom accommodation in Holymoorside
An outdoor patio with a table, chairs, a hot tub, and a view of a golf course.

2. Cherry Tree Farm

Cherry Tree Farm
3.0 star property
Chesterfield
Cherry Tree Farm
A stone house with a lawn, 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
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 €656
includes taxes & fees
21 Oct - 22 Oct
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
The price is €527
includes taxes & fees
17 Nov - 18 Nov
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
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 €396
includes taxes & fees
23 Oct - 24 Oct
Little Mill
A bathroom with a freestanding bathtub, a wooden vanity with drawers, a toilet, and a mirror.

7. The Old Stables

The Old Stables
3.5 star property
Chesterfield
The price is €865
includes taxes & fees
2 Nov - 3 Nov
The Old Stables
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 €774
includes taxes & fees
24 Oct - 25 Oct
Cherry Tree Cottage
A brick house with a white door, a small garden, and a patio with a table and chairs.

9. Cedar Cottage

Cedar Cottage
3.5 star property
Chesterfield
The price is €469
includes taxes & fees
30 Oct - 31 Oct
Cedar Cottage
A wooden cabin with a fenced backyard, a small porch, and a stone wall in the background.

10. Thorntree Lodge

Thorntree Lodge
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (1 review)
The price is €570
includes taxes & fees
23 Oct - 24 Oct
Thorntree Lodge
A backyard with a small lawn, a wooden shed, and a tall bamboo fence.

11. Overton

Overton
2.0 star property
Chesterfield
Overton
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
The price is €611
includes taxes & fees
1 Nov - 2 Nov
Harry's Lodge
A stone building with a pitched roof, a small porch, and a stone wall in the background.

13. Riber View Barn

Riber View Barn
3.0 star property
Chesterfield
Riber View Barn
A stone building with a gravel driveway and two potted plants.

14. The Cottage

The Cottage
3.0 star property
Chesterfield
The price is €744
includes taxes & fees
26 Oct - 27 Oct
The Cottage
A wooden deck with a wicker sofa and a round table, overlooking a green landscape.

15. Cuckoo Nest

Cuckoo Nest
3.5 star property
Chesterfield
The price is €396
includes taxes & fees
31 Oct - 1 Nov
Cuckoo Nest
A stone house with a large glass bay window, a patio with outdoor furniture, and a well-maintained lawn.

16. Swallows Barn

Swallows Barn
3.5 star property
Chesterfield
Swallows Barn
Interior

17. The Loft

The Loft
3.5 star property
Chesterfield
The price is €718
includes taxes & fees
1 Nov - 2 Nov
The Loft
An outdoor dining area with wicker chairs, a glass table, and a hot tub in the background.

18. Moor Farm Cottage

Moor Farm Cottage
3.0 star property
Chesterfield
The price is €740
includes taxes & fees
2 Nov - 3 Nov
Moor Farm Cottage
A stone building with a large window, a stone archway, and a garden with hedges and a flower bed.

19. The Tack Room Cottage

The Tack Room Cottage
3.0 star property
Chesterfield
The price is €670
includes taxes & fees
2 Nov - 3 Nov
The Tack Room Cottage
A stone building with two arched windows, a small door, and a garden with various plants.

20. 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 €450
includes taxes & fees
27 Oct - 28 Oct
The Old Chapel
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesterfield Hotel Reviews

The Welcome Inn Hotel

The Welcome Inn Hotel

8/10 Good
"Free parking on site. Room was clean and roomy. Tea and coffee making facilities. Clean bathroom. Great value for money. Would definitely stay again."
Becci 1-night trip
Posted 3 hours ago
The Welcome Inn Hotel

Find out more about Chesterfield

Chesterfield Cottages information

Number of reviews
12
Accommodation
2008 Cottages
Lowest Price
€396
Highest Price
€865

Frequently asked questions

How much do cottages in Chesterfield cost?
Cottages in Chesterfield range between €396 and €865 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. Cosy 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 2008 cottages in Chesterfield. Whether you're travelling with the kids or organising 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 €396 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 Theatre 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.