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

Search Vacation Homes in Chesterfield

  • 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
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Chesterfield vacation homes

A stone house with a wooden bench in front, a car parked nearby, and a stone wall in the background.

1. Robin Hood Tower

Robin Hood Tower
3.0 star property
Matlock
10.0 out of 10, Exceptional, (14 reviews)
"This is a wonderfully quirky and unique place to stay. The accommodation is just perfect. Hosts Steve and Elaine have created a tranquil and idyllic tiny retreat at Robin Hood Tower. Comms were great and Steve showed us around, sharing local history and top tips for our trip. Canal side walks were glorious. A magical stay."
United Kingdom
Heidi
The price is SAR 827
SAR 992 total
includes taxes & fees
11 Oct - 12 Oct
Robin Hood Tower
Dining

2. 3-bed House - Sleeps 6 - Free Parking - Garden

3-bed House - Sleeps 6 - Free Parking - Garden
3.0 star property
Sheffield
The price is SAR 511
SAR 1,000 total
includes taxes & fees
8 Oct - 9 Oct
3-bed House - Sleeps 6 - Free Parking - Garden
A residential street with houses, a parked white car, and a tree.

3. Bens Green, parking, spacious home, near the Peaks

Bens Green, parking, spacious home, near the Peaks
South Yorkshire
The price is SAR 552
SAR 994 total
includes taxes & fees
6 Oct - 7 Oct
Bens Green, parking, spacious home, near the Peaks
Restaurant

4. Old Nags Head

Old Nags Head
3.0 star property
Hope Valley
10.0 out of 10, Exceptional, (3 reviews)
"Perfect location. Warm staff. Great room."
United Kingdom
Kai
The price is SAR 435
SAR 530 total
includes taxes & fees
8 Oct - 9 Oct
Old Nags Head
A corner house with a bay window, a white door, and a brick wall.

5. Cozy Double Bedroom with Private Bathroom

Cozy Double Bedroom with Private Bathroom
Hillsborough
The price is SAR 152
SAR 232 total
includes taxes & fees
20 Oct - 21 Oct
Cozy Double Bedroom with Private Bathroom
A hotel room with a bed, a nightstand, a lamp, a mirror, and a door.

6. 3-bed House - Sleeps 6 - Free Parking - Garden

3-bed House - Sleeps 6 - Free Parking - Garden
Sheffield
3-bed House - Sleeps 6 - Free Parking - Garden
A stone building with a sign reading "Kingfisher Lodge."

7. Stone built self-catering lodge in stunning location

Stone built self-catering lodge in stunning location
Froggatt
10.0 out of 10, Exceptional, (12 reviews)
"Amazing location enjoyed every minute we stayed here Katie and Rod were very friendly beautiful little cottage"
United Kingdom
Michelle C.
The price is SAR 472
SAR 552 total
includes taxes & fees
7 Oct - 8 Oct
Stone built self-catering lodge in stunning location
A corner house with a bay window, a door, and a small fenced area.

8. Serene Homes Sheffield | Peaceful Ensuite Velux Room for Rest & Focus

Serene Homes Sheffield | Peaceful Ensuite Velux Room for Rest & Focus
Hillsborough
The price is SAR 159
SAR 363 total
includes taxes & fees
3 Nov - 4 Nov
Serene Homes Sheffield | Peaceful Ensuite Velux Room for Rest & Focus
A bedroom with a bed, a chair, a desk, a TV, and a mirror.

9. Stylish Private Guest Suite | Sleeps 5 | Free Parking |Near City & Peak District

Stylish Private Guest Suite | Sleeps 5 | Free Parking |Near City & Peak District
Hillsborough
10.0 out of 10, Exceptional, (1 review)
"Nice property, lots of sleeping space, outside space good too. No cooker or oven, so don't plan to cook whilst staying. Lots of nice restaurants and take aways."
United States
Reena P.
The price is SAR 358
SAR 669 total
includes taxes & fees
2 Nov - 3 Nov
Stylish Private Guest Suite | Sleeps 5 | Free Parking |Near City & Peak District
A sauna with a wooden interior, marble walls, and a pink ceiling.

10. Suite 1 Private Jacuzzi Spa Hot Tub & Sauna

Suite 1 Private Jacuzzi Spa Hot Tub & Sauna
Sheffield
The price is SAR 706
SAR 810 total
includes taxes & fees
6 Oct - 7 Oct
Suite 1 Private Jacuzzi Spa Hot Tub & Sauna
A neatly made bed with a plaid blanket, a decorative pillow, and a rolled towel on the bed.

11. 3 Bed House Sleeps 5 - Free Parking - Tv & Wifi

3 Bed House Sleeps 5 - Free Parking - Tv & Wifi
3.0 star property
Sheffield
6.0 out of 10, (1 review)
"Overall if you are a dirtbag climber and just in sheffield for a quick trip this place totally gets the job done. Our biggest issues were that there was no shower curtain so the bathroom flooded when anyone showered, none of the bathrooms had soap, and overall just super limited amenities. Also the trash out front was absolutely overflowing and was all over the yard. Honestly would stay again in a pinch, just would come with lower expectations."
United Kingdom
Elizabeth
The price is SAR 431
SAR 517 total
includes taxes & fees
9 Oct - 10 Oct
3 Bed House Sleeps 5 - Free Parking - Tv & Wifi
A modern living room with a sofa, coffee table, and a TV. There is a kitchen in the background with a stove, oven, and cabinets.

12. No 4

No 4
3.5 star property
Mansfield
6.0 out of 10, (3 reviews)
"Just what we required for our family of 4 for a last minute accommodation with well equipped kitchen, comfortable beds and washing machine. Easy secure parking, friendly neighbours and lovely park at the end of the street."
Australia
Graham
The price is SAR 659
SAR 791 total
includes taxes & fees
18 Oct - 19 Oct
No 4
A modern bedroom with two beds, a window with blinds, a radiator, and a dark door.

13. Cheerful and Cosy 4 bedroom House

Cheerful and Cosy 4 bedroom House
Upperthorpe
10.0 out of 10, Exceptional, (2 reviews)
"Really comfortable, really helpful communicative host and we would definitely stay again"
United Kingdom
Joanna B.
The price is SAR 805
SAR 1,064 total
includes taxes & fees
6 Oct - 7 Oct
Cheerful and Cosy 4 bedroom House
A house with a brick exterior, a glass door, and a small balcony.

14. Hayeswood Lodge Luxury Accommodation

Hayeswood Lodge Luxury Accommodation
3.5 star property
Ilkeston
10.0 out of 10, Exceptional, (35 reviews)
"Great place - very clean and a lovely little breakfast"
United Kingdom
Ian
The price is SAR 579
SAR 695 total
includes taxes & fees
19 Oct - 20 Oct
Hayeswood Lodge Luxury Accommodation
Private kitchen

15. 4 bedroom house opposite Northern General Hospital

4 bedroom house opposite Northern General Hospital
Longley
The price is SAR 738
SAR 992 total
includes taxes & fees
6 Oct - 7 Oct
4 bedroom house opposite Northern General Hospital
Raised garden beds with plants against a brick wall.

16. Clean Spacious Walkley Home, 8pp, Free Street Parking

Clean Spacious Walkley Home, 8pp, Free Street Parking
South Yorkshire
The price is SAR 464
SAR 836 total
includes taxes & fees
7 Oct - 8 Oct
Clean Spacious Walkley Home, 8pp, Free Street Parking
A modern living room with a sofa, a coffee table, a fireplace, and a flat-screen TV mounted on the wall.

17. URBA Luxury Stays 3 Bed Home Sheffield Central

URBA Luxury Stays 3 Bed Home Sheffield Central
Norfolk Park
The price is SAR 920
SAR 1,357 total
includes taxes & fees
1 Nov - 2 Nov
URBA Luxury Stays 3 Bed Home Sheffield Central
A modern kitchen with a dining area, featuring a herringbone wood floor, a central island with chairs, and a window with blinds.

18. Stylish house in Rotherham/Sheffield area, with free private parking.

Stylish house in Rotherham/Sheffield area, with free private parking.
Rotherham
The price is SAR 604
SAR 849 total
includes taxes & fees
8 Oct - 9 Oct
Stylish house in Rotherham/Sheffield area, with free private parking.
A room with a black door, a fireplace, a grey sofa, and a round coffee table.

19. Hip Hideaway in the Trendiest part of Town

Hip Hideaway in the Trendiest part of Town
Sharrow
The price is SAR 572
SAR 771 total
includes taxes & fees
6 Oct - 7 Oct
Hip Hideaway in the Trendiest part of Town
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

mour Hotel

mour Hotel

10/10 Excellent
"Good atmosphere, and location, quite and peaceful"
Wendy 1-night trip
Posted 6 hours ago
mour Hotel