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 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Chesterfield vacation rentals

Private kitchen

1. Commuters Getaway Chesterfield

Commuters Getaway Chesterfield
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (2 reviews)
The price is P6,276
P9,528 total
includes taxes & fees
Sep 1 - Sep 2
Commuters Getaway Chesterfield
Dining

2. Cherry Tree Farm

Cherry Tree Farm
3.0 star property
Chesterfield
The price is P119,387
P143,265 total
includes taxes & fees
Sep 8 - Sep 9
Cherry Tree Farm
Terrace/patio

3. 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 P6,276
P9,528 total
includes taxes & fees
Sep 1 - Sep 2
2bed - Garden-pets-freeparking-m1connections
Living area

4. Overton

Overton
2.0 star property
Chesterfield
The price is P39,814
P47,776 total
includes taxes & fees
Aug 26 - Aug 27
Overton
Fridge, microwave, oven, stovetop

5. a Quiet Semi Rural Property Located in Bolsover

a Quiet Semi Rural Property Located in Bolsover
3.5 star property
Chesterfield
The price is P8,418
P10,498 total
includes taxes & fees
Sep 11 - Sep 12
a Quiet Semi Rural Property Located in Bolsover
Outdoor spa tub

6. Wigley Farm House Cottage

Wigley Farm House Cottage
3.0 star property
Chesterfield
Wigley Farm House Cottage
Exterior

7. Riber View Barn

Riber View Barn
3.0 star property
Chesterfield
Riber View Barn
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
The price is P45,259
P54,311 total
includes taxes & fees
Sep 2 - Sep 3
Cherry Tree Cottage
Interior

9. Swallows Barn

Swallows Barn
3.5 star property
Chesterfield
Swallows Barn
Fridge, dishwasher, electric kettle, cookware/dishes/utensils

10. Cuckoo Nest

Cuckoo Nest
3.5 star property
Chesterfield
The price is P23,124
P27,749 total
includes taxes & fees
Sep 4 - Sep 5
Cuckoo Nest
3 bedrooms, WiFi (free), individually decorated, individually furnished

11. Cedar Cottage

Cedar Cottage
3.5 star property
Chesterfield
The price is P27,438
P32,926 total
includes taxes & fees
Sep 15 - Sep 16
Cedar Cottage
Interior

12. The Loft at The George

The Loft at The George
3.5 star property
Chesterfield
The price is P39,036
P46,843 total
includes taxes & fees
Aug 31 - Sep 1
The Loft at The George
Outdoor dining

13. Moor Farm Cottage

Moor Farm Cottage
3.0 star property
Chesterfield
The price is P43,350
P52,020 total
includes taxes & fees
Sep 4 - Sep 5
Moor Farm Cottage
4 bedrooms, WiFi (free), individually decorated, individually furnished

14. The Old Stables

The Old Stables
3.5 star property
Chesterfield
The price is P50,563
P60,675 total
includes taxes & fees
Aug 31 - Sep 1
The Old Stables
Fireplace

15. The Cottage

The Cottage
3.0 star property
Chesterfield
The price is P43,632
P52,359 total
includes taxes & fees
Sep 11 - Sep 12
The Cottage
Garden

16. The Tack Room Cottage

The Tack Room Cottage
3.0 star property
Chesterfield
The price is P41,723
P50,068 total
includes taxes & fees
Aug 31 - Sep 1
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.
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Top Chesterfield Hotel Reviews

The Orchard Hotel & Restaurant

The Orchard Hotel & Restaurant

10/10 Excellent
"Really"
Carol 1-night trip
Posted 8 hours ago
The Orchard Hotel & Restaurant

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.

How many vacation rentals will I find in Chesterfield?

With 47 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.