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.

A historic building with black and white timber framing, a prominent clock tower, and a pointed spire in the background.

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Our top choices for Chesterfield cottages

Cuckoo Nest

Chesterfield

includes taxes & fees

26 Jun - 27 Jun

Bathurst Cottage is a delightful three bedroom detached cottage.

Chesterfield

Valerie Thompson

includes taxes & fees

25 Jun - 26 Jun

Bryn Tor - The Gardener's House

Bolsover, near Chesterfield

includes taxes & fees

23 Jun - 24 Jun

2 bedroom accommodation in Holymoorside

Holymoorside

V & P Roberts

includes taxes & fees

18 Jul - 19 Jul

Harry's Lodge

Chesterfield

includes taxes & fees

1 Jul - 2 Jul

Overton

Chesterfield

includes taxes & fees

29 Jun - 30 Jun

Shire Cottage at Top Butterley Farm

Chesterfield

Ian

includes taxes & fees

7 Jul - 8 Jul

Moor Farm Cottage

Chesterfield

includes taxes & fees

29 Jun - 30 Jun

Thorntree Lodge

Chesterfield

includes taxes & fees

5 Jul - 6 Jul

The Cottage

Chesterfield

includes taxes & fees

29 Jun - 30 Jun

The Old Chapel

Chesterfield

Mark

includes taxes & fees

4 Jul - 5 Jul

Swallows Barn

Chesterfield

includes taxes & fees

23 Jul - 24 Jul

Wigley Farm House Cottage

Chesterfield

includes taxes & fees

26 Jun - 27 Jun

The Old Stables

Chesterfield

includes taxes & fees

29 Jun - 30 Jun

The Loft at The George

Chesterfield

includes taxes & fees

28 Jun - 29 Jun

Cherry Tree Cottage

Chesterfield

toyin

includes taxes & fees

28 Jun - 29 Jun

Little Mill

Chesterfield

Yvonne

includes taxes & fees

27 Jun - 28 Jun

The Loft

Chesterfield

includes taxes & fees

25 Jun - 26 Jun

Cherry Tree Farm

Chesterfield

includes taxes & fees

29 Jun - 30 Jun

Woodthorpe Cruck Cottage

Chesterfield

Anthony

includes taxes & fees

9 Jul - 10 Jul

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Top Chesterfield Hotel Reviews

The Orchard Hotel & Restaurant

8/10 Good

"The first room we were allocated was facing the bar and atrium so we asked to change to a room that faced outwards. The restaurant was good though a bit expensive. Coffee was also quite expensive."

mour Hotel

10/10 Excellent

"Convenient location close to M1 (but not too close). Great car park (with several EV chargers) surrounded by trees. Huge reception with comfy sofas. Great check in by polite and efficient staff. Good size room with masculine decor. A little worn around the edges but very clean. The extremely firm bed suited us. We liked the views from the 4th floor (there were lifts). We used the hotel to break a long journey. The restaurant was slightly pricey, but our food was good. We didn’t stay for breakfast."

Derby Mickleover Hotel, BW Signature Collection

10/10 Excellent

"A great getaway hotel with plenty to do and Derby and the Peak District in easy reach. Pros: The Suite with the Balcony was a lovely spacious room, comfortable enormous bed, all the facilities you'd want and a very large bathroom. We made good use of the pool and gym and both a very well maintained and enjoyable. The hotel atrium is such an inviting space with bar and restaurant both lovely and easy to find. Parking is great too, and again access to the main road is close but you still feel firmly out in the countryside. Cons: the Air Con was a little baffling and just wouldn't come on the whole time we were there. The room itself is a bit dated, but that's kind of charming in it's own way."

Find out more about Chesterfield

Chesterfield Cottages information

Number of reviews	14
Accommodation	1829 Cottages
Lowest Price	£328
Highest Price	£1,628

Frequently asked questions

How much do cottages in Chesterfield cost?

Cottages in Chesterfield range between £328 and £1,628 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 9.4. 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 1829 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 £328 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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Brimington Holiday Rentals

Search Chesterfield Cottages

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chesterfield cottages

Cuckoo Nest

Bathurst Cottage is a delightful three bedroom detached cottage.

Bryn Tor - The Gardener's House

2 bedroom accommodation in Holymoorside

Harry's Lodge

Overton

Shire Cottage at Top Butterley Farm

Moor Farm Cottage

Thorntree Lodge

The Cottage

The Old Chapel

Swallows Barn

Wigley Farm House Cottage

The Old Stables

The Loft at The George

Cherry Tree Cottage

Little Mill

The Loft

Cherry Tree Farm

Woodthorpe Cruck Cottage

Find holiday rentals that suit your style

Top Chesterfield Hotel Reviews

The Orchard Hotel & Restaurant

Find out more about Chesterfield

Chesterfield Cottages information

Frequently asked questions

Explore a world of travel with Expedia