
Family-friendly holiday rentals in Chesterfield
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Top-rated family-friendly rentals in Chesterfield
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Oakdale - Our Quest retreat
Idyllically situated at the entrance to Hardwick Wood, Wingerworth, 2 miles from Chesterfield and all amenities, yet totally secluded. Close to Chatsworth & Peak District. Fully fitted kitchen all appliances including tumble drier & dishwasher. Underfloor zoned central heating. Log burner. Fully fitted bathroom with bath and shower. Separate shower/wc. Fully fitted bedrooms with ample wardrobes and drawers ideally suited to a family of 4. Sleeps 4 in one double and 1 set of bunks, cot available

The Kennels
Kick off your walking boots, wash down your bike or just park up the car, this brand new converted kennels is the place to relax for a few days. Peaceful and away from it all but close enough to explore the beauty of the Peak District and Chatsworth House. Matlock is a couple of miles away with restaurants, shops and amenities. You can start exploring from the door step; we can help with guides, directions and recommendations. The room can be configured as a luxury Super King or twin beds.

Wasp Nest Cottage, Peak District
Sitting on the edge of the Peak District, a stone’s throw from open fields, woodland and moors - sits a 19th Century cosy mill worker’s cottage. Two pubs and a shop are within easy walking distance and Chatsworth House is a beautiful 7 mile wander over the hill. Marvel at the lovely centuries old tree slice, coffee table and huge slice of elm breakfast bar, enjoy chopping boards, pottery and soft furnishings from the local artisans - just some of the magic the Peak District has to offer.

Cosy studio apartment close to Peak District
Cosy,private ,self contained upstairs studio with own entrance , double bed with en suite, dual ring halogen hob ,combination microwave and oven , television with free sat ,free wifi ,integrated fridge freezer ,breakfast bar and stools . Comfy chairs to relax! On the main bus route into Chesterfield and the Peak District ,10 mins to Chatsworth,20 mins to Bakewell and lots of walks in the area. Many bars ,coffee shops and restaurants within walking distance . We look forward to meeting you.

The Garden Room
The Annexe is self contained in the garden of our home in Wingerworth. Private entrance through small conservatory . Shower room , fridge, kettle, toaster , microwave. Cereals, bread, butter and preserves provided. Close to countryside and Peak District National Park . On drive parking. Bus stops nearby to Chesterfield and Derby with links by bus/train from Chesterfield Rail Station. Good local walks and Chatsworth Estate 20 minutes drive. Excellent Pub/Restaurant 5 minutes walk away.

Exclusive & Beautiful Modern Studio Flat
Located on Green Lane, traffic is busy at peak times of the day, however this private studio is perfect for access to the Peak District. There is a kitchen, a spacious bathroom, pull-down double bed (only a small 4 ft double). The flat is best suited for a single person but if you are in a couple and the bed is ok, then this will suit you. The Peak district is just a short car ride away. Restaurants, supermarkets; train station and buses will take you to Sheffield or chesterfield.

Chesterfield -Peak District-Chatsworth-EV Charger
Enjoy our ground floor studio, private entrance, bathroom, kitchenette with fridge freezer, microwave, double bed, wall-mounted TV. PAYG EV Charger - Ideal for business travellers and couples seeking a relaxing break. Located on a quiet, tree-lined avenue. Minutes from Chatsworth Road's bars and restaurants. Close to the Peak District, Chatsworth House, Buxton, Bakewell, and Matlock, guest access via a coded key lock. Nestled near the Hipper Valley bike trail for a peaceful retreat.

The Long Hall 2 bed ground floor annexed apartment
Long Hall has been lovingly converted into a 6-person, ground floor, annexed apartment, within a quiet housing estate, a short distance from the Peak District. Two large double bedrooms, with rainfall shower en-suites, and a large open-plan living area dining and kitchen area and a large, shared enclosed patio and garden area Long Hall suits leisure and tourist staycations, as well as trade or professional workers, who wish for a home from home. SKY Sports and Movies included

Self-Catering, Log Burner, Cosy, Peak District
Welcome to Leveret! Our cosy retreat in the heart of the picturesque Peak District. Lovingly designed to provide you with the perfect blend of comfort and rustic charm! Unwind by the crackling warmth of the log burner, while relaxing on the comfortable modern furnishings! Leveret features a well-appointed king-size bedroom, fully equipped kitchen complete with modern appliances, and bathroom with bath and shower over. Private outdoor space & BBQ area in peaceful surroundings.

2 Bed Apartment at the Corner House
A ground floor two double bedroom apartment in a converted 1800s home which has recently undergone further high-spec refurbishment, used solely for guests. The open plan kitchen/diner holds a sofa bed is perfect for a relaxing stay. The property is within walking distance to Chesterfield town centre and train station with an allocated parking space for one car. This is perfect for anyone commuting or working in the area as well as visiting the Peak District.

Woolley Lodge Farm Retreat
A brand new fully furnished wooden lodge situated within the grounds of a working farm, with views across open countryside. The cabin has been furnished to a high standard and includes a double bedroom with double bed. The kitchen has a full size fridge with small freezer, full size oven and a microwave. It has a small bathroom with a full size corner shower. It has its own entrance, parking and a beautiful decked area and fire pit outside

The Loft
Immaculate Twin Loft Room with en-suite shower. Room accessed by the key in a Keysafe adjacent to the private door. Car parking for 1 vehicle available. 5 minute walk to Ringwood Hall, Canal, 3 takeaways and the Hollingwood Public House. 5 minute drive to M1 junction29a. Room has free Wifi, tea/coffee making facilities, television, microwave, fridge, clothes rail and 2 chest of drawers. Towels and bedding provided.
Popular amenities for Chesterfield family-friendly rentals
Family-friendly home rentals with a hot tub

Hunters Cottage. Wheatsheaf Mews

Lizzy’s Luxury Cottage

Jack's Cottage, Curbar

Bridgefoot Cottage - Wild Swimming & Hot Tub

Luxury Peak District Cottage with Hot Tub

Pear Tree Lodge with private HOT TUB and garden

The Granary

Courtyard Cottage -With Japanese Whirlpool Bath
Family- and pet-friendly home rentals

Cosy Quiet Cottage In Pilsley

Country Cottage with great outside space & views

The Annexe - Belle Vue House

The Hideaway, Great views, garden & location

Charming fully equipped home 5min to Peak District

Swift Retreat - converted farm building

Quaint 2 bed cottage, ideally located for walking

Quiet hideaway in Matlock with far reaching views
Family-friendly home rentals with a pool

Caravan near Tissington Trail

Luxury Peak District Home - 2 miles from Ashbourne

Two bed annex apartment

Indoor Pool, Pizza Oven, Close to Alton Towers

Cosy Woodside Cottage, indoor pool, nr Chatsworth

Loki’s Lodge@ Ashbourne Heights holiday park

Family Home Getaway - Hot Tub, Sauna & Swim Spa

Uppergate Farmhouse Apartment
Quick stats about holiday rentals that are family-friendly in Chesterfield
Total rentals
60 properties
Nightly prices starting at
$65 SGD before taxes and fees
Total number of reviews
3.8K reviews
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wifi availability
60 properties include access to wifi
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- Peak District national park
- Alton Towers
- Etihad Stadium
- Chatsworth House
- The Quays
- Drayton Manor Theme Park
- Harewood House
- Sundown Adventureland
- Lincoln Castle
- Mam Tor
- Royal Armouries Museum
- Tatton Park
- Holmfirth Vineyard
- Crucible Theatre
- The Nottinghamshire Golf & Country Club
- Rufford Park Golf and Country Club
- Science and Industry Museum
- Shrigley Hall Golf Course
- IWM North
- John Rylands Library
- Cavendish Golf Club
- Daisy Nook Country Park
- Derwent Valley Mills
- Manchester Central Library