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

Search Chesterfield Cottages

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

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

Exterior

1. 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
$374 nightly
The price is $374
Sep 17 - Sep 18
Total with taxes and fees
2 bedroom accommodation in Holymoorside
Exterior

2. Carr House Farm

Carr House Farm
2.0 star property
Chesterfield
$500 nightly
The price is $600
Sep 17 - Sep 18
Total with taxes and fees
Carr House Farm
Property grounds

3. Bryn Tor - The Gardener's House

Bryn Tor - The Gardener's House
Bolsover, near Chesterfield
$746 nightly
The price is $746
Sep 6 - Sep 7
Total with taxes and fees
Bryn Tor - The Gardener's House
Outdoor dining

4. Cherry Tree Farm

Cherry Tree Farm
3.0 star property
Chesterfield
$1,816 nightly
The price is $2,179
Sep 22 - Sep 23
Total with taxes and fees
Cherry Tree Farm
Property grounds

5. Little Mill

Little Mill
2.0 star property
Chesterfield
$375 nightly
The price is $450
Sep 22 - Sep 23
Total with taxes and fees
Little Mill
Terrace/patio

6. Overton

Overton
2.0 star property
Chesterfield
$645 nightly
The price is $774
Sep 28 - Sep 29
Total with taxes and fees
Overton
Cottage | Exterior

7. Cedar Cottage

Cedar Cottage
3.5 star property
Chesterfield
$445 nightly
The price is $534
Sep 13 - Sep 14
Total with taxes and fees
Cedar Cottage
Terrace/patio

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
$734 nightly
The price is $880
Sep 29 - Sep 30
Total with taxes and fees
Cherry Tree Cottage
Balcony

9. Cuckoo Nest

Cuckoo Nest
3.5 star property
Chesterfield
$375 nightly
The price is $450
Sep 7 - Sep 8
Total with taxes and fees
Cuckoo Nest
Exterior

10. Wigley Farm House Cottage

Wigley Farm House Cottage
3.0 star property
Chesterfield
$695 nightly
The price is $834
Sep 12 - Sep 13
Total with taxes and fees
Wigley Farm House Cottage
Cottage | Exterior

11. Harry's Lodge

Harry's Lodge
3.0 star property
Chesterfield
$579 nightly
The price is $695
Oct 2 - Oct 3
Total with taxes and fees
Harry's Lodge
Cottage | Exterior

12. 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
$512 nightly
The price is $512
Sep 26 - Sep 27
Total with taxes and fees
The Old Chapel
Exterior

13. Riber View Barn

Riber View Barn
3.0 star property
Chesterfield
$393 nightly
The price is $472
Sep 26 - Sep 27
Total with taxes and fees
Riber View Barn
Exterior

14. The Loft at The George

The Loft at The George
3.5 star property
Chesterfield
$633 nightly
The price is $759
Sep 14 - Sep 15
Total with taxes and fees
The Loft at The George
Cottage | Outdoor dining

15. Moor Farm Cottage

Moor Farm Cottage
3.0 star property
Chesterfield
Moor Farm Cottage
Property grounds

16. 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
$688 nightly
The price is $825
Sep 24 - Sep 25
Total with taxes and fees
Woodthorpe Cruck Cottage
Exterior

17. The Cottage

The Cottage
3.0 star property
Chesterfield
$706 nightly
The price is $847
Sep 11 - Sep 12
Total with taxes and fees
The Cottage
Exterior

18. Thorntree Lodge

Thorntree Lodge
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (1 review)
$540 nightly
The price is $648
Sep 26 - Sep 27
Total with taxes and fees
Thorntree Lodge
Garden

19. The Tack Room Cottage

The Tack Room Cottage
3.0 star property
Chesterfield
$636 nightly
The price is $763
Sep 27 - Sep 28
Total with taxes and fees
The Tack Room 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.
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

WILDES INNS

WILDES INNS

10/10 Excellent
"Lovely staff"
Navid 1-night trip
Posted 4 hours ago
WILDES INNS

Find out more about Chesterfield

Chesterfield Cottages information

Number of reviews
9
Accommodation
2043 Cottages
Lowest Price
$450
Highest Price
$2,179

Frequently asked questions

How much do cottages in Chesterfield cost?
Cottages in Chesterfield range between $450 and $2,179 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 9.6.
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 $450 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.

Explore a world of travel with Expedia