Search Family-Friendly Hotels in Chesterfield

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Check availability on Chesterfield Family-Friendly Hotels

Tonight
30 Dec - 31 Dec
Tomorrow
31 Dec - 1 Jan
This weekend
2 Jan - 4 Jan
Next weekend
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, (438)
"Handy to motorway, food service great and room comfortable"
United Kingdom
Lynne
The price is ฿3,142
฿3,770 total
includes taxes & fees
2 Jan - 3 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
30 Jan - 31 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
12 Jan - 13 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
12 Jan - 13 Jan 2026
The Old Stables
Cottage | Interior
The Loft at The George

The Loft at The George

The Loft at The George
3.5 star property
Chesterfield
The price is ฿19,654
฿23,585 total
includes taxes & fees
12 Jan - 13 Jan 2026
The Loft at The George
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 ฿21,659
฿25,990 total
includes taxes & fees
3 Jan - 4 Jan 2026
Woodthorpe Cruck Cottage
Exterior
The Maynard

The Maynard

The Maynard
4.0 star property
Grindleford
9.0 out of 10, Wonderful, (33)
"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, (1320)
"Always a lovely place to stay with great amenities and fantastic staff. "
United Kingdom
Rob
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, (197)
"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
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
"We have stayed at this hotel many times when visiting family and are always so impressed by the friendly helpful staff at reception. The hotel is always very clean and the rooms are large with an enormous bed! Breakfast is excellent too. "
Lesley 1-night trip
Posted 3 days ago
DoubleTree by Hilton Nottingham-Gateway
Twin Oaks Hotel

Twin Oaks Hotel

10/10 Excellent
"Thank you so much for a lovely clean friendly stay, the hotel was clean and well looked after hotel room was nice and warm and clean staff was soooo friendly and really made my stay welcoming thank you so much."
Gemma 1-night trip
Posted 9 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.