Search Family-Friendly Hotels in Chesterfield

Start date: Check-in selected.
To Date
End date: Check-out

  • 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 availability on Chesterfield Family-Friendly Hotels

Tonight
27 Dec - 28 Dec
Tomorrow
28 Dec - 29 Dec
Next weekend
2 Jan - 4 Jan
In two weeks
9 Jan - 11 Jan

Our top choices for Chesterfield family-friendly hotels

Deluxe Family Room for 2 adults and 2 children additional cost of £10 per night double sofa bed | Desk, free cots/infant beds, rollaway beds, free WiFi
Twin Oaks Hotel

Twin Oaks Hotel

Twin Oaks Hotel
3.0 star property
Chesterfield
8.8 out of 10, Excellent, (435)
"Handy to motorway, food service great and room comfortable"
United Kingdom
Lynne
The price is ฿3,142
฿3,770 total
includes taxes & fees
20 Jan - 21 Jan 2026
Twin Oaks Hotel
House | Private kitchen | Fridge, microwave, oven, stovetop
2bed - Garden-pets-freeparking-m1connections

2bed - Garden-pets-freeparking-m1connections

2bed - Garden-pets-freeparking-m1connections
2.0 star property
Chesterfield
10.0 out of 10, Exceptional, (1)
"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 ฿3,718
฿4,461 total
includes taxes & fees
1 Jan - 2 Jan 2026
2bed - Garden-pets-freeparking-m1connections
Cottage | Interior
The Loft

The Loft

The Loft
3.5 star property
Chesterfield
The price is ฿21,149
฿25,379 total
includes taxes & fees
10 Jan - 11 Jan 2026
The Loft
Cottage | Interior
The Old Stables

The Old Stables

The Old Stables
3.5 star property
Chesterfield
The price is ฿25,458
฿30,549 total
includes taxes & fees
10 Jan - 11 Jan 2026
The Old Stables
Cottage | Interior
Woodthorpe Cruck Cottage

Woodthorpe Cruck Cottage

Woodthorpe Cruck Cottage
3.5 star property
Chesterfield
9.0 out of 10, Wonderful, (2)
"Amazing cottage in amazing location.will definetly be back"
United Kingdom
Anthony
The price is ฿21,261
฿25,513 total
includes taxes & fees
3 Jan - 4 Jan 2026
Woodthorpe Cruck Cottage
Exterior
The Maynard

The Maynard

The Maynard
4.0 star property
Grindleford
9.2 out of 10, Wonderful, (32)
"Lovely room, wonderful staff"
United Kingdom
Renita
The price is ฿2,670
฿3,204 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Maynard
Lobby sitting area
The Orchard Hotel & Restaurant

The Orchard Hotel & Restaurant

The Orchard Hotel & Restaurant
4.0 star property
Nottingham
9.4 out of 10, Exceptional, (1313)
"The Staff are exceptional, very friendly and helpful, the restaurant food was first class, and portions generous, the breakfast buffet had everything imaginable. The whole design and ambience of the building is modern yet very cosy. Definitely a great find and a hotel and restaurant I will be revisiting "
United Kingdom
William
The Orchard Hotel & Restaurant
Bar (on property)
DoubleTree by Hilton Sheffield City

DoubleTree by Hilton Sheffield City

DoubleTree by Hilton Sheffield City
4.0 star property
Sheffield
9.0 out of 10, Wonderful, (196)
"Spacious roooms, comfy beds, nice clean bathroom"
United Kingdom
Rebecca
The price is ฿2,344
฿2,813 total
includes taxes & fees
11 Jan - 12 Jan 2026
DoubleTree by Hilton Sheffield City
Bar (on property)
Nottingham Belfry Hotel & Spa

Nottingham Belfry Hotel & Spa

Nottingham Belfry Hotel & Spa
4.0 star property
Nottingham
8.4 out of 10, Very good, (1004)
"Very good clean hotel with good staff"
United Kingdom
Derek
The price is ฿2,460
฿2,952 total
includes taxes & fees
11 Jan - 12 Jan 2026
Nottingham Belfry Hotel & Spa
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

Top Chesterfield Hotel Reviews

DoubleTree by Hilton Nottingham-Gateway

DoubleTree by Hilton Nottingham-Gateway

10/10 Excellent
"Excellent stay, lovely team - a beautiful hotel"
Revinder 1-night trip
Posted 5 days ago
DoubleTree by Hilton Nottingham-Gateway
Twin Oaks Hotel

Twin Oaks Hotel

10/10 Excellent
"Handy to motorway, food service great and room comfortable"
Lynne 1-night trip
Posted 12 days ago
Twin Oaks Hotel

Frequently asked questions

What's Chesterfield like for family-friendly holidays?
The welcoming destination of Chesterfield is a good choice if you've been thinking about a trip with your children. The parks, theatres and restaurants are just a few things that make this an attractive family holiday destination. Take to the air and fly into Doncaster (DSA-Sheffield), which is located 24.3 mi (39.1 km) from the city centre.
What's the best family accommodation in Chesterfield?
Twin Oaks Hotel is a hotel with a restaurant and free parking, and it's a top choice on Expedia for families.
When's the best time to book a family-friendly holiday in Chesterfield?
The hottest months are usually July and August, with an average temperature of 15°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chesterfield is 714 mm.
What's there to see and do with your family in Chesterfield?
While you and your family are visiting Chesterfield, you may want to explore some child-friendly attractions such as Peak District National Park and Chesterfield Market. Make sure that you have lots of time for activities such as SMH Group Stadium and Hardwick Hall-Derbyshire Country Park.
What's the best way for us to get around Chesterfield?
If you want to venture outside the area, hop on a train at Chesterfield Station. Chesterfield may not have many public transport options, so consider a car rental to maximise your time.