The tow path on the Chesterfield canal on a bright sunny day

Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Chesterfield vacation rentals

A kitchen with a black stove, white cabinets, a wooden cutting board, and potted plants on the windowsill.

1. Commuters Getaway Chesterfield

Commuters Getaway Chesterfield
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (2 reviews)
The price is ￥15,367
￥23,641 total
includes taxes & fees
Sep 1 - Sep 2
Commuters Getaway Chesterfield
A sunlit room with a large window, a sofa, a table, and a potted plant.

2. Overton

Overton
2.0 star property
Chesterfield
The price is ￥103,711
￥124,453 total
includes taxes & fees
Sep 3 - Sep 4
Overton
A compact kitchen with a black refrigerator, a toaster, a sink, and a stove.

3. a Quiet Semi Rural Property Located in Bolsover

a Quiet Semi Rural Property Located in Bolsover
3.5 star property
Chesterfield
The price is ￥21,928
￥27,346 total
includes taxes & fees
Sep 11 - Sep 12
a Quiet Semi Rural Property Located in Bolsover
A hot tub under a wooden pergola with a stone wall and greenery in the background.

4. 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 ￥117,895
￥141,474 total
includes taxes & fees
Sep 3 - Sep 4
Cherry Tree Cottage
A patio with stone tiles, a wooden fence, and a flower bed with plants and flowers.

5. 2bed - Garden-pets-freeparking-m1connections

2bed - Garden-pets-freeparking-m1connections
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (1 review)
"Property is self catering house at edge of the town. Spacious and decent kitchen. Road quiet (liked that) and easy access to nature reserve/countryside walks. Parking a bit of an issue but didn’t detract from our stay. "
United Kingdom
Philip
The price is ￥15,367
￥23,641 total
includes taxes & fees
Sep 8 - Sep 9
2bed - Garden-pets-freeparking-m1connections
A bedroom with a bed, a wardrobe, a window with curtains, and a door leading to another room.

6. Carr House Farm

Carr House Farm
2.0 star property
Chesterfield
The price is ￥80,316
￥96,379 total
includes taxes & fees
Sep 16 - Sep 17
Carr House Farm
A cozy room with a wooden ceiling, a sofa, and a window with curtains.

7. Swallows Barn

Swallows Barn
3.5 star property
Chesterfield
The price is ￥188,183
￥225,821 total
includes taxes & fees
Sep 3 - Sep 4
Swallows Barn
A conservatory with a dining table set for six, surrounded by large windows offering a view of a garden.

8. Cherry Tree Farm

Cherry Tree Farm
3.0 star property
Chesterfield
The price is ￥291,848
￥350,217 total
includes taxes & fees
Sep 22 - Sep 23
Cherry Tree Farm

9. Little Mill

Little Mill
2.0 star property
Chesterfield
The price is ￥60,237
￥72,284 total
includes taxes & fees
Sep 3 - Sep 4
Little Mill
A stone house with a sloped roof, a green door, and a mailbox attached to the wall.

10. 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
The price is ￥110,526
￥132,631 total
includes taxes & fees
Sep 24 - Sep 25
Woodthorpe Cruck Cottage
An outdoor dining area with wicker chairs, a glass table, and a hot tub in the background.

11. Moor Farm Cottage

Moor Farm Cottage
3.0 star property
Chesterfield
The price is ￥112,921
￥135,505 total
includes taxes & fees
Sep 4 - Sep 5
Moor Farm Cottage
A hot tub in a backyard with a stone wall and a grassy lawn.

12. Wigley Farm House Cottage

Wigley Farm House Cottage
3.0 star property
Chesterfield
The price is ￥111,632
￥133,958 total
includes taxes & fees
Sep 12 - Sep 13
Wigley Farm House Cottage
A living room with a stone wall, a fireplace, leather sofas, and a television.

13. The Cottage

The Cottage
3.0 star property
Chesterfield
The price is ￥120,105
￥144,126 total
includes taxes & fees
Sep 11 - Sep 12
The Cottage
A stone building with two arched windows, a small door, and a garden with various plants.

14. 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 ￥82,232
￥82,232 total
includes taxes & fees
Sep 26 - Sep 27
The Old Chapel
A bedroom with a bed, a nightstand, a chair, a window with curtains, and a door.

15. Cedar Cottage

Cedar Cottage
3.5 star property
Chesterfield
The price is ￥71,474
￥85,769 total
includes taxes & fees
Sep 13 - Sep 14
Cedar Cottage
A stone building with a large window, a stone archway, and a garden with hedges and a flower bed.

16. The Tack Room Cottage

The Tack Room Cottage
3.0 star property
Chesterfield
The price is ￥102,237
￥122,684 total
includes taxes & fees
Sep 4 - Sep 5
The Tack Room Cottage
A rural landscape with a stone wall, a small building, and a view of the countryside.

17. Shire Cottage at Top Butterley Farm

Shire Cottage at Top Butterley Farm
3.0 star property
Chesterfield
9.0 out of 10, Wonderful, (2 reviews)
"The location is fine and the view beautiful. The owners were very helpful when needed. A most enjoyable stay."
Australia
Ian
The price is ￥73,390
￥73,390 total
includes taxes & fees
Sep 3 - Sep 4
Shire Cottage at Top Butterley Farm
A stone building with a sign reading "The George Country Pub & Dining."

18. The Loft at The George

The Loft at The George
3.5 star property
Chesterfield
The price is ￥101,684
￥122,021 total
includes taxes & fees
Sep 6 - Sep 7
The Loft at The George
A bedroom with a bed, a television, a nightstand, and a bathroom visible through a doorway.

19. The Old Stables

The Old Stables
3.5 star property
Chesterfield
The price is ￥131,711
￥158,053 total
includes taxes & fees
Sep 4 - Sep 5
The Old Stables
A cozy cabin-style interior with a kitchen, dining area, and seating space.

20. Thorntree Lodge

Thorntree Lodge
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (1 review)
The price is ￥86,763
￥104,116 total
includes taxes & fees
Sep 26 - Sep 27
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

Leopold Hotel

Leopold Hotel

10/10 Excellent
"Very central for bars etc. And a lovely courtyard with restaurants and live music at weekends. They have a convenient parking deal not far away. A beautiful building with excellent rooms. The breakfast was amazing and came with a great deal included with our room. We will definitely be staying again. ."
Steve 1-night trip
Posted 1 hour ago
Leopold Hotel

Find out more about Chesterfield

Search for holiday rentals in Chesterfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesterfield using one of the methods below:

  • View our selection of featured holiday rentals in Chesterfield
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Look no further and take a look at our great range of rental properties in Chesterfield!

Frequently asked questions

Can I find a vacation rental in Chesterfield?

Yes, you can find vacation rentals in Chesterfield close to Clay Cross Active, or you can choose a secluded option if you want a relaxing stay. Our travelers say Chesterfield has a good selection of top-notch restaurants and lively bars. Make sure you have time to check out the churches and parks during your trip.

What are some of the best vacation home rentals that Chesterfield has to offer?

Cosy Barn in The Peak District National Park - ideal for walkers. Dog friendly .: Visitors like this Chesterfield vacation home rental. It offers a fireplace, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and an oven.

How many vacation rentals will I find in Chesterfield?

With 44 Expedia vacation rentals, you're sure to find just the right place for your Chesterfield stay.

What can I see and do in Chesterfield?

Enjoy the outdoors at Peak District National Park and Queen's Park, or simply take in cultural attractions like Barrow Hill Roundhouse Railway Centre and Hotel Van Dyk Theater. Bolsover Castle and Hardwick Hall are other places to visit while you're in town.

What are vacation rentals like in Chesterfield?

Vacation rentals are private properties you can stay in for several days or longer in Chesterfield. Vacation rentals feature extras such as WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for a family trip or a small group gathering.