A stone path winding through a valley with a sunset in the background.

Chesterfield Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Chesterfield vacation rentals

A patio with stone tiles, a wooden fence, and a flower bed with plants and flowers.

1. 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 ₩135,294
₩205,398 total
includes taxes & fees
Nov 22 - Nov 23
2bed - Garden-pets-freeparking-m1connections
A conservatory with a dining table set for six, surrounded by large windows offering a view of a garden.

2. Cherry Tree Farm

Cherry Tree Farm
3.0 star property
Chesterfield
The price is ₩2,231,134
₩2,677,361 total
includes taxes & fees
Nov 24 - Nov 25
Cherry Tree Farm
A hot tub under a wooden pergola with a stone wall and greenery in the background.

3. Cherry Tree Cottage

Cherry Tree Cottage
3.0 star property
Chesterfield
10.0 out of 10, Exceptional, (3 reviews)
"The property was lovely and clean beautiful views and was so relaxing"
United Kingdom
Lorraine
The price is ₩878,127
₩1,053,752 total
includes taxes & fees
Nov 24 - Nov 25
Cherry Tree Cottage
A stone building with a water wheel and a staircase.

4. Little Mill

Little Mill
3.0 star property
Chesterfield
10.0 out of 10, Exceptional, (1 review)
"Lovely little cottage in a beautiful setting. Great walks around. Bed comfortable and lovely warm shower. The welcome package was very helpful as I arrived late on Sunday and forgot the English shops closed early!"
United Kingdom
Rona
The price is ₩492,655
₩591,193 total
includes taxes & fees
Nov 3 - Nov 4
Little Mill
A kitchen with white cabinets, a wooden beam ceiling, a microwave, and a wooden dining table.

5. Carr House Farm

Carr House Farm
3.0 star property
Chesterfield
The price is ₩656,873
₩788,251 total
includes taxes & fees
Nov 3 - Nov 4
Carr House Farm
A sunlit room with a large window, a sofa, a table, and a potted plant.

6. Overton

Overton
3.0 star property
Chesterfield
The price is ₩848,210
₩1,017,845 total
includes taxes & fees
Nov 16 - Nov 17
Overton
A bedroom with a bed, a television, a nightstand, and a bathroom visible through a doorway.

7. The Old Stables

The Old Stables
3.5 star property
Chesterfield
The price is ₩1,077,212
₩1,292,654 total
includes taxes & fees
Nov 3 - Nov 4
The Old Stables
A cozy cabin-style interior with a kitchen, dining area, and seating space.

8. Thorntree Lodge

Thorntree Lodge
3.5 star property
Chesterfield
10.0 out of 10, Exceptional, (1 review)
The price is ₩706,181
₩847,421 total
includes taxes & fees
Nov 12 - Nov 13
Thorntree Lodge
A bedroom with a bed, a nightstand, a chair, a window with curtains, and a door.

9. Cedar Cottage

Cedar Cottage
3.5 star property
Chesterfield
The price is ₩581,737
₩698,077 total
includes taxes & fees
Nov 12 - Nov 13
Cedar Cottage
A rural road with stone walls and a stone building with a sign.

10. Riber View Barn

Riber View Barn
3.0 star property
Chesterfield
Riber View Barn
A wooden deck with outdoor seating and a glass door leading to a covered area.

11. Harry's Lodge

Harry's Lodge
3.0 star property
Chesterfield
The price is ₩760,828
₩912,994 total
includes taxes & fees
Nov 30 - Dec 1
Harry's Lodge
A living room with a stone wall, a fireplace, leather sofas, and a television.

12. The Cottage

The Cottage
3.0 star property
Chesterfield
The price is ₩841,120
₩1,009,348 total
includes taxes & fees
Nov 12 - Nov 13
The Cottage
A stone building with a large window, a stone archway, and a garden with hedges and a flower bed.

13. The Tack Room Cottage

The Tack Room Cottage
3.0 star property
Chesterfield
The price is ₩832,124
₩998,549 total
includes taxes & fees
Nov 12 - Nov 13
The Tack Room Cottage
A stone building with a wooden door, a hose, and a horse in the background.

14. The Loft

The Loft
3.5 star property
Chesterfield
The price is ₩894,915
₩1,073,894 total
includes taxes & fees
Nov 3 - Nov 4
The Loft
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

Sandman Signature Sheffield Quays Hotel

Sandman Signature Sheffield Quays Hotel

8/10 Good
"Lovely experience, beautiful room with a balcony overlooking the quay. Friendly and helpful staff. Parking was easy, good size carpark right outside and a fair price compared to other hotels in the area. Only downside was breakfast, everything was left to run low without being replenished and when we ordered some poached eggs, we had to wait ages and when they did come they were sat in a pool of water on a plate and were still raw on the inside which put us off the rest of our breakfast."
Adam 1-night trip
Posted 1 hour ago
Sandman Signature Sheffield Quays Hotel

Find out more about Chesterfield

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

  • View our selection of featured Vacation rentals in Chesterfield
  • Use the map to find apartments and other Vacation homes in the Chesterfield neighbourhood you prefer
  • Enter your travel dates to view the best deals on Vacation rentals in Chesterfield while they last

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?

Old Nags Head: You might want to consider this vacation home rental near Chesterfield, which comes with free WiFi so you can feel at home during your trip. Kitchen amenities include a stovetop, a microwave, and kitchenware.

How many vacation rentals will I find in Chesterfield?

With 43 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. Chesterfield Market and Bolsover Castle 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.