Best Cottages in Chesterfield in 2026

Q: Are there any family-friendly cottages in Chesterfield?

Get comfortable at Thorntree Lodge , a 3.5-star cottage just a quick drive from town. Amenities here include WiFi and a fireplace. Another family-friendly pick where you can swap the urban jungle for fresh air and nature is Shire Cottage At Top Butterley Farm . WiFi and a fridge help make this 3-star cottage a traveller favourite. Once you've checked in and dropped off your bags, there are plenty of family-friendly attractions to visit in and around Chesterfield. Chesterfield Market and Bolsover Castle are two popular options.

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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

Holymoorside

V & P Roberts

includes taxes & fees

17 Sept - 18 Sept

A stone building with two wooden doors and a small window.

2. Carr House Farm

Chesterfield

includes taxes & fees

16 Sept - 17 Sept

A balcony with a view of a field, a table with chairs, and a potted plant.

3. Bryn Tor - The Gardener's House

Bolsover, near Chesterfield

includes taxes & fees

25 Sept - 26 Sept

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

4. Cherry Tree Farm

Chesterfield

includes taxes & fees

22 Sept - 23 Sept

A stone building with a sloped roof, wooden doors, and a gravel driveway.

5. Little Mill

Chesterfield

includes taxes & fees

22 Sept - 23 Sept

A backyard with a small lawn, a wooden shed, and a tall bamboo fence.

6. Overton

Chesterfield

includes taxes & fees

28 Sept - 29 Sept

A brick house with a white door, a small garden, and a patio with a table and chairs.

7. Cedar Cottage

Chesterfield

includes taxes & fees

13 Sept - 14 Sept

A hot tub under a wooden pergola with a stone wall and greenery in the background.

8. Cherry Tree Cottage

Chesterfield

Lorraine

includes taxes & fees

29 Sept - 30 Sept

A wooden deck with a wicker sofa and a round table, overlooking a green landscape.

9. Cuckoo Nest

Chesterfield

includes taxes & fees

8 Sept - 9 Sept

A stone house with a well-maintained garden, a stone wall, and a clear sky.

10. Wigley Farm House Cottage

Chesterfield

includes taxes & fees

12 Sept - 13 Sept

A rustic lodge with a sign reading "Harry's Lodge," surrounded by lush greenery and a stone wall.

11. Harry's Lodge

Chesterfield

includes taxes & fees

2 Oct - 3 Oct

A stone building with two arched windows, a small door, and a garden with various plants.

12. The Old Chapel

Chesterfield

Mark

includes taxes & fees

26 Sept - 27 Sept

A stone building with a pitched roof, a small porch, and a stone wall in the background.

13. Riber View Barn

Chesterfield

includes taxes & fees

26 Sept - 27 Sept

A stone building with multiple windows, a door, and a signboard.

14. The Loft at The George

Chesterfield

includes taxes & fees

18 Sept - 19 Sept

An outdoor dining area with wicker chairs, a glass table, and a hot tub in the background.

15. Moor Farm Cottage

Chesterfield

A stone house with a sloped roof, a green door, and a mailbox attached to the wall.

16. Woodthorpe Cruck Cottage

Chesterfield

Anthony

includes taxes & fees

24 Sept - 25 Sept

A stone building with a gravel driveway and two potted plants.

17. The Cottage

Chesterfield

includes taxes & fees

11 Sept - 12 Sept

A wooden cabin with a fenced backyard, a small porch, and a stone wall in the background.

18. Thorntree Lodge

Chesterfield

includes taxes & fees

26 Sept - 27 Sept

A stone building with a large window, a stone archway, and a garden with hedges and a flower bed.

19. The Tack Room Cottage

Chesterfield

includes taxes & fees

27 Sept - 28 Sept

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Top Chesterfield Hotel Reviews

The Orchard Hotel & Restaurant

10/10 Excellent

"Lovely hotel have stayed there several times and staff always helpful"

Leonardo Hotel Nottingham

10/10 Excellent

"Our room at the Leonardo Hotel was very clean , we had a great view from our room .Everything was great the bed and pillows were so comfortable. The staff were all so helpful, nothing to much trouble , and they were all very friendly. Breakfast was excellent Everything for everyone , nothing bad at all to say about it. In the everning we had a nice drink at the bar , it was well equipped with everything , and a nice spacious area to relax . The Leonardo is a great place stay we definitely recommend it ."

Ringwood Hall Hotel & Spa, BW Signature Collection

10/10 Excellent

"The welcome on arrival was very friendly, helpful and efficient. My luggage was taken to and from my room, which is great. All the staff were very friendly. Meals were lovely, just too much for my appetite. Enjoyed walking and sitting in the grounds too."

Find out more about Chesterfield

Chesterfield Cottages information

Number of reviews	10
Accommodation	2038 Cottages
Lowest Price	£277
Highest Price	£1,616

Frequently asked questions

How much do cottages in Chesterfield cost?

Cottages in Chesterfield range between £277 and £1,616 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?

Chesterfield offers multiple cottages with a total average guest review rating of 9.8. Thorntree Lodge is a terrific option if you're a fan of nature and a laid-back pace. Guests staying at this 3.5-star stay will have use of a garden and a fireplace. Shire Cottage At Top Butterley Farm is another popular choice. This 3-star cottage offers individually decorated rooms and WiFi.

How many cottages are there in Chesterfield?

Take your pick of 2038 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?

The Rumblings 2 is one of the most affordable cottages in Chesterfield. It offers individually decorated rooms and WiFi. Another favourite that's easy on the finances is The Rumblings 1. Conveniences here include individually decorated rooms and WiFi. Rates for cottages start at only £277 per night, which means you can afford to spend more time relaxing in the great outdoors. Seeing free attractions in Chesterfield will stretch your travel dollars even further. Chesterfield Market and Hardwick Hall-Derbyshire Country Park are favourites. With the dollars you save, why not explore some more? 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?

Get comfortable at Thorntree Lodge, a 3.5-star cottage just a quick drive from town. Amenities here include WiFi and a fireplace. Another family-friendly pick where you can swap the urban jungle for fresh air and nature is Shire Cottage At Top Butterley Farm. WiFi and a fridge help make this 3-star cottage a traveller favourite. Once you've checked in and dropped off your bags, there are plenty of family-friendly attractions to visit in and around Chesterfield. Chesterfield Market and Bolsover Castle are two popular options.

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.

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Chesterfield Holiday Rentals

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Our top choices for Chesterfield cottages