Cottages in Chesterfield

26 available cottage rental offers

7 nights
2
1
  • airbnb
  • booking
  • stayz
  • expedia
  • hotelscom
  • tripadvisor
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Chesterfield cottages
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

26 Best cottages in Chesterfield

Top-Rated Family Cottages in Chesterfield

Give the family a holiday with real character and story at family cottages in Chesterfield.

Hopton, Two Dales, Derbyshire - Chesterfield
No reviews

Hopton, Two Dales, Derbyshire

cottage, Matlock
This 4-bedroom, 3-bathroom cottage in Hopton, near Two Dales, is situated 500 metres from local shops and 3 kilometres from the Plough Inn pub, providing convenient access to the Peak District National Park and the towns of Matlock and Bakewell, with attractions such as Haddon Hall and Chatsworth House nearby.
This family-friendly holiday home accommodates up to 8 guests, featuring a ground-floor en-suite bedroom, a private patio, a shared lawn, and a well-equipped open-plan living space, with conference facilities also available for hire.
Cottage ∙ 1 Bedroom ∙ 3 Guests - Chesterfield
No reviews

Cottage ∙ 1 Bedroom ∙ 3 Guests

cottage, Barlow
This Barlow holiday cottage is situated within 50 acres of conservation pastures and woodland, offering a tranquil natural environment close to the Peak District National Park and the South Yorkshire border.
This one-bedroom lodge accommodates up to three guests and features an open-plan living space with a gas fire, a zip and link super kingsize bed, complimentary Wi-Fi, and a patio with shared garden furniture, ideal for bird and wildlife spotting.
Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
9.3 129 reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage
This first-floor apartment in Matlock, Derbyshire, offers stunning views of Riber Castle and Matlock church, and is a short drive (approximately 10km) from Bakewell and Ashover, the filming location for parts of the Peak Practice TV series.
Knowleston Place cottage sleeps four guests in two bedrooms, features a modern kitchen with a fridge and dishwasher, and provides free parking and Wi-Fi; enjoy its open-plan living area with mullioned windows overlooking Riber Castle.
Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
No reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage
This Victorian terraced house at Lime Grove Walk 11 in Matlock offers a family-friendly base within 300 meters of the town centre and provides convenient access to the Peak District National Park.
This two-bedroom dwelling accommodates up to four guests with a farmhouse-style kitchen, a sitting room featuring a woodburning stove, and an enclosed rear garden with bike storage, ideal for exploring local attractions such as Hall Leys Park and Heights of Abraham.

Best Chesterfield cottages with a kitchen

Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
No reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage, Tansley
Oakwood Mews is a contemporary holiday home located in the rural village of Tansley, Derbyshire, just 3.2 kilometres from Matlock and on the edge of the Peak District National Park.
This single-storey cottage offers accommodation for four guests in two king-size bedrooms, featuring underfloor heating, a well-equipped kitchen/diner, a private enclosed courtyard, and is conveniently situated for exploring attractions such as Chatsworth House and Carsington Water.
Cottage ∙ 5 Bedrooms ∙ 11 Guests - Chesterfield
8.4 3 reviews

Cottage ∙ 5 Bedrooms ∙ 11 Guests

cottage
This five-bedroom terraced house is located in Darwin Lake Holiday Village, Derbyshire, approximately 5.1 km from Matlock and within easy reach of Matlock Bath and Bakewell.
The property offers spacious three-storey accommodation sleeping up to ten guests, featuring an open-plan living/kitchen/dining area, four bedrooms (including one ground-floor twin), en-suite shower rooms, a patio garden, and ample off-road parking; nearby activities include exploring Chatsworth House and Haddon Hall.
Cottage ∙ 3 Bedrooms ∙ 6 Guests - Chesterfield
9.6 7 reviews

Cottage ∙ 3 Bedrooms ∙ 6 Guests

cottage
This Derbyshire stone cottage, situated in Darwin Lake Holiday Village near the village of Two Dales, offers easy access to the Peak District National Park, Bakewell (approx. 10km), and Matlock (approx. 15km), placing you within easy reach of Haddon Hall and Chatsworth House.
The three-bedroom property sleeps six, features an open-plan living area with modern appliances, a ground-floor twin room with en-suite, two upstairs bedrooms with zip-and-link beds and en-suite facilities, plus a garden, parking, and internet access; pets are welcome.
80 M² Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
9.5 57 reviews

80 M² Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage
Wild Hill Cottage, a semi-detached bungalow, is situated on the edge of the Peak District National Park, approximately 4km from Sutton-in-Ashfield, 8km from Mansfield, and 16km from Chesterfield, offering easy access to attractions like Hardwick Hall and the Heights of Abraham.
This 80 square metre ground-floor property sleeps four in two bedrooms, one bathroom, and boasts a kitchen with fridge, microwave, and dishwasher, plus a garden, parking, and internet access; nearby pubs include the Carnarvon Arms, White Hart, and Woodend Stonehouse.

Frequently asked questions about cottages in Chesterfield

  • When is the best time to rent a cottage in Chesterfield?

    Spring and autumn are lovely times to visit Chesterfield, as the weather is mild and the crowds are smaller. You'll enjoy the changing colours of the leaves in autumn and the blossoming flowers in spring. Summer is also a popular time to visit, but it can get busy.
  • What are the best cottages in Chesterfield?

    Among the cottages in Chesterfield, Wasp Nest Cottage - Peak District, Chatsworth Cottage and Peak District Perfection With Luxury Bath-sleeps 6 are the most popular ones.

  • What are the can't-miss sights in Chesterfield?

    The Crooked Spire is a must-see, of course! It's a unique and iconic landmark that you won't find anywhere else. Also, don't miss the Chesterfield Museum and Art Gallery, the beautiful Queen's Park, and the historic Chesterfield Market.
  • What are the best cottages with a pool in Chesterfield?

    The best cottage with a pool in Chesterfield is Cottage ∙ 2 Bedrooms ∙ 5 Guests.

  • Why consider renting a cottage in Chesterfield for your stay?

    Renting a cottage offers a more relaxed and comfortable experience than staying in a hotel. You'll have your own space, kitchen facilities, and often a garden or patio. It's a great way to feel more at home and enjoy a peaceful getaway.
  • What are the best cottages with a jacuzzi in Chesterfield?

    The best cottages with a jacuzzi in Chesterfield are The Olde Coach House - Cottage With Hot Tub, Tawny Owl Barn and Boundary Cottage.

  • Can you easily explore Chesterfield on foot or by bike?

    Yes, Chesterfield is a very walkable town. The town centre is compact and most attractions are within easy reach. You can also hire bikes from various locations in the town, which is a great way to explore the surrounding countryside.
  • What are the best cottages for families and kids in Chesterfield?

    The best cottages for families and kids in Chesterfield are Wasp Nest Cottage - Peak District, Chatsworth Cottage and Peak District Perfection With Luxury Bath-sleeps 6.

  • What are the best restaurants in Chesterfield with nature views?

    The Crooked Spire Bistro offers stunning views of the Crooked Spire and the town centre. The Old Vicarage is also a great option, with a beautiful garden and a peaceful atmosphere. You can enjoy a delicious meal while surrounded by nature.
  • What are the best pet friendly cottages in Chesterfield?

  • What family-friendly activities are available in Chesterfield?

    Queen's Park is a great place for a family day out, with a playground, boating lake, and plenty of open space for running around. The Chesterfield Museum and Art Gallery also has interactive exhibits that are fun for children. For a more active day, try the Chesterfield Bowl bowling alley or the Chesterfield Climbing Centre.
  • What are the best cottages with parking in Chesterfield?

Popular destinations

View All Cottages with a Hot Tub in Chesterfield

Retreat to a private sanctuary of hot bubbles right in your room at city cottages with a hot tub in Chesterfield.

Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
10 47 reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage
This semi-detached holiday home is located just a short distance from Matlock, a charming town in the heart of the Peak District National Park, offering breathtaking views of the Derbyshire Dales. The cottage is situated on the edge of the National Park, making it an ideal base for exploring the stunning scenery and outdoor activities on offer.
The cottage has two bedrooms and can comfortably accommodate up to four guests. It offers a range of amenities, including a fully equipped kitchen, a spacious garden, a hot tub, and a conservatory, making it perfect for relaxing and enjoying the beautiful surroundings.
The Loft, Pet Friendly, Character Holiday Cottage In Millthorpe - Chesterfield
8.0 1 review

The Loft, Pet Friendly, Character Holiday Cottage In Millthorpe

cottage, Dronfield
This converted Grade II listed stable, located in Millthorpe on the edge of the Peak District National Park, offers splendid valley views and is a short drive from Chatsworth House and Bakewell.
This 130 square meter cottage sleeps up to 7 guests across 3 bedrooms and features a separate building with a sauna and hot tub, alongside a garden with barbecue facilities and parking.

Elite Pet-Friendly Cottages in Chesterfield

Welcome every member of the family, including your pet, at pet-friendly cottages in Chesterfield.

Mill Farm Cottages - Kingfisher - Chesterfield
No reviews

Mill Farm Cottages - Kingfisher

cottage, Barlow near Bakewell
This self-catering lodge in Barlow, Derbyshire, is situated within 50 hectares of conservation land and offers convenient access to the Peak District National Park and South Yorkshire, with Chatsworth House located approximately 11 kilometres away.
This pet-friendly cottage accommodates two guests in one bedroom and features an open-plan ground floor with a gas fire, dining area, and kitchen, plus complimentary Wi-Fi and the option for on-site fishing for an additional charge.
Cottage ∙ 1 Bedroom ∙ 2 Guests - Chesterfield
No reviews

Cottage ∙ 1 Bedroom ∙ 2 Guests

cottage, Ashover
This first-floor apartment, Little Mill, is located in Ashover, Derbyshire, set within an old mill beside the River Amber, 8 kilometers from Matlock and close to Chatsworth House and Haddon Hall.
This pet-friendly, family-friendly cottage sleeps two guests in one bedroom, offering a well-equipped open-plan living space with a kitchen, a sitting area with an electric fire, an en-suite shower room, and a garden with river views, plus shared grounds with picnic facilities and bike storage.
Cottage ∙ 4 Bedrooms ∙ 5 Guests - Chesterfield
No reviews

Cottage ∙ 4 Bedrooms ∙ 5 Guests

cottage
This accessible bungalow, Havendale, is located in historic Chesterfield, Derbyshire, just 1.4 kilometers from the medieval market town centre and its famous 'Crooked Spire', with the Peak District National Park, Chatsworth House, and Haddon Hall within easy driving distance.
This architecturally designed, single-storey property accommodates up to five guests in four bedrooms, featuring an open-plan living space with an accessible kitchen, a woodburning stove, and wide bifold doors leading to an enclosed south-facing garden with a barbecue, whilst pets and families are welcome.
The Loft At The George, Pet Friendly In Clay Cross - Chesterfield
No reviews

The Loft At The George, Pet Friendly In Clay Cross

cottage, Chesterfield
The Loft at The George, a five-bedroom holiday home in Clay Cross, is situated approximately 8km from Chesterfield town centre, offering easy access to the Crooked Spire church and Queens Park, and within easy reach of the Peak District National Park.
This 145 square metre property features an open-plan living area, a fully equipped kitchen, two bathrooms, and sleeps eight guests comfortably, including family-friendly amenities such as a travel cot and highchair; occasional weekend live music is available at the on-site gastro pub.

Book Top-Rated Luxury Cottages in Chesterfield

Escape the urban noise inside an intimate, design-forward timber sanctuary at luxury cottages in Chesterfield.

Cottage ∙ 1 Bedroom ∙ 2 Guests - Chesterfield
No reviews

Cottage ∙ 1 Bedroom ∙ 2 Guests

cottage, Barlow

Top-Rated Cottages with a Pool in Chesterfield

Enjoy an exclusive swim in total privacy right in your own backyard at city cottages featuring a swimming pool in Chesterfield.

Cottage ∙ 2 Bedrooms ∙ 4 Guests - Chesterfield
10 8 reviews

Cottage ∙ 2 Bedrooms ∙ 4 Guests

cottage
©2026 cozycozy.com