- The Old Farmhouse
- Greenwell Cottage in Chesterfield
- Alton Hall Cottage in Alton
- Shelduck Cottage in Holmfirth
- The Continent in Ticknall
- The Stone Barn
- Hillcrest in Bolsover
- Broadmeadows Farm
- De Ferrers in Alport
- Elm Cottage
- Bradley Hall in Matlock
- Pine Cottage
- Waterside Barn at Bradbourne
- Juglans Barn in Belper
- Loadbrook Barn in Load Brook
- Gadley House East Wing
- Cokaynes in Alport
- Tissington Ford Barn at Bradbourne
- The Water Mill at Bradbourne
- The Barn in Ashbourne
- The Cottage at Bridge Farm
- The Milking Parlour
- The Cow Shed
- The Manor House in Alport
- Valley View Barn at Bradbourne
Chesterfield Group Cottages
49 Cottages Found
- Private hot tub for 8
- Four ensuite bedrooms
- Parking for 5 cars
- Peak District location
- Historical 18th century features
- Hot tub seats 8
- Parking for 6 cars
- 4 bedrooms sleep 8
- Enclosed secure garden
- Canal walks from doorstep
- Five bedrooms sleep eight
- Open plan kitchen diner
- Enclosed garden with BBQ
- Wood burner lounge area
- Walking distance to attractions
- Hot tub with panoramic views
- Ground floor luxury bungalow
- Sleeps 11 across four bedrooms
- Parking for six cars
- Peak District location
- Hot tub seats four
- Five spacious bedrooms
- Ground floor bedroom available
- Stunning valley views
- Walking distance to attractions
- Sleeps 8 with hot tub
- Working farm setting experience
- Peak District gateway location
- Pet-friendly welcomes 3 dogs
- Private parking 3 cars
- Grade II Listed Georgian House
- 8-Seater Private Hot Tub
- Peak District National Park Location
- Firepit and Pizza Oven
- Enclosed South-Facing Garden
- Private hot tub included
- Sleeps 10 guests comfortably
- Riverside Derbyshire location
- Peak District 12.5 miles
- Five bedrooms three bathrooms
- Lakeside cottage sleeps seven
- Four bathrooms including en-suites
- Free fishing day and night
- Peak District National Park access
- Ample parking for groups
- Historic Domesday Book cottage
- Indoor heated swimming pool
- Private hot tub relaxation
- 14-acre grounds to explore
- Peak District walking routes
- Sleeps 8 in family bedrooms
- Wildflower meadow with grazing animals
- Underfloor heating throughout barn
- Castleton caves 8 minutes away
- Village shop and pub walkable
- Private hot tub with speakers
- Games room with pool table
- Sleeps eleven guests comfortably
- Five bedrooms flexible arrangements
- Peak District walking trails nearby
- Private hot tub garden
- Indoor swimming pool access
- Four bedrooms sleep 10
- Peak District countryside views
- Games room with WiFi
- Spectacular Derwent Valley views
- Sleeps 9 across 4 bedrooms
- 1.5 acres enclosed dog fields
- Parking for 4 cars
- Near Chatsworth House
- Four en-suite bedrooms
- Private hot tub garden
- Games room with entertainment
- Five minutes to Matlock
- Spectacular Peak District views
- Four bedrooms sleeps eight
- Private garden with BBQ
- Peak District location
- Step-free accessible entrance
- Private driveway parking
- Sleeps 10 across five bedrooms
- Stunning Peak District valley views
- Open-plan living with woodburning stove
- Ground floor bedroom and facilities
- Walking distance to excellent pub
- Private hot tub for eight
- Four luxury bedrooms available
- Two separate living room spaces
- Walking distance Bolsover Castle
- Modern kitchen with island
- Private hot tub relaxation
- Peak District walking distance
- Sleeps seven guests comfortably
- Three bathrooms prevent queues
- Lakeside location with woodland
- Historic barn conversion sleeps 14
- Indoor heated swimming pool access
- Games room with billiards
- Six ensuite bedrooms available
- Peak District National Park location
Looking for the perfect getaway with friends or family? Group cottages in Chesterfield offer everything you need for an unforgettable stay. Choose from large properties that sleep 12 or more guests. Our group accommodation lets you escape the everyday grind with homes that include cottages near golf courses for keen players. We also offer hen party accommodation and stag party retreats with wood-burning stoves for cosy evenings and pet-friendly large houses for your furry friends.
This historic market town is famous for the Crooked Spire at St Mary's Church and the medieval Market Place near Chesterfield Museum and the Pomegranate Theatre. Browse independent shops and cafes along Knifesmithgate before exploring the canal and Peak District National Park nearby. Visit Revolution House where the Glorious Revolution was planned or wander through Queen's Park with its boating lake. The town's railway heritage shines at Barrow Hill Roundhouse and Stephenson Memorial Hall. Hardwick Hall sits just beyond the area alongside Bolsover Castle on the edge of the Peak District.
The nearby Peak District makes this the ideal base for a dog-friendly break on your luxury group holiday with walks and attractions close by. Perfect for a family reunion getaway or large family gatherings where everyone can relax. Your large family will love a Chesterfield group cottage for making memories.