Holiday Cottages near Sheffield

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Your Sheffield, Sheffield search returned 70 cottages

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A property's star rating is the average of the star ratings received from guests that wish for their review to be published

  • Sleeps5
  • Bedrooms4
  • Pet FriendlyYes

    5.0

    Perfect

  • Sykes rating

Havendale is a stunning single-storey holiday home in Chesterfield, Derbyshire, boasting accessible features, a woodburning stove, and an enclosed garden. Matlock 9.5 miles; Chatsworth 10.7 miles; Bakewell 13 miles. (Ref. 1167060)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher


for 7 nights From £1260

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.8

    Outstanding

  • Sykes rating

A charming semi-detached cottage resting in the village of Bolsterstone on the fringes of the Peak District National Park. Pet friendly. Patio garden. Electric fire. Peaceful location. Close to reservoir. Sheffield 8.8 miles; Holmfirth 15 miles. (Ref. 1066255)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • 10% off - Wed 6th Jan to 29th Jan 2027


for 7 nights From £469

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.8

    Outstanding

  • Sykes rating

Pine Cottage, a charming pet-friendly cottage near Hathersage, Derbyshire, within Peak District National Park, features an enclosed garden and rural views. Curbar 5.3 miles; Castleton 6 miles. (Ref. 1198284)

  • Pets go free
  • Off-road parking
  • Ground floor bedroom
  • Washing machine


for 7 nights From £580

Last booked 2 days ago
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  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.6

    Outstanding

  • Sykes rating

A charming retreat based on the outskirts of Oughtibridge. Pet-friendly. Open-plan living. Hot tub. Sheffield 6.3 miles; Rotherham 9.5 miles. (Ref. 993255)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Hot Tub
  • Dishwasher
  • Washing machine


for 7 nights From £1046

Last booked yesterday
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  • Sleeps8
  • Bedrooms4
  • Pet FriendlyYes

    4.6

    Outstanding

  • Sykes rating

A charming detached stone-built cottage, set in lovely countryside. Two miles from the town of Stocksbridge in Yorkshire. Hot tub. WiFi. Pet-friendly. Good touring base for the Peak District. (Ref. 952074)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights From £904

  • Sleeps4
  • Bedrooms1
  • Pet FriendlyYes

    4.9

    Outstanding

  • Sykes rating

Highview Stables is a pet-friendly cottage resting in the bustling market town of Chesterfield in Derbyshire with a woodburning stove and lovely views. Chatsworth 6.2 miles; Bakewell 8.9 miles; Matlock 9.9 miles. (Ref. 1169996)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Ground floor bedroom
  • Hot Tub
  • Dishwasher
  • Washing machine


for 7 nights From £528

Last booked yesterday
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  • Sleeps9
  • Bedrooms4
  • Pet FriendlyYes

    4.7

    Outstanding

  • Sykes rating

A detached farmhouse located in the village of Hathersage in Hope Valley. Woodburners. Pet-friendly. Four bedrooms. Castleton 5 miles. Curbar 5 miles. (Ref. 952361)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights From £1225

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.9

    Outstanding

  • Sykes rating

A superb two-bedroom bungalow resting on the outskirts of Dronfield, near Chesterfield, Derbyshire. Family-friendly. Large partially enclosed garden. Dog friendly. Peak District. Bakewell 12.8 miles; Matlock 13.2 miles. (Ref. 1084691)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 7 nights From £554

Last booked yesterday
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  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.8

    Outstanding

  • Sykes rating

A stylish converted cottage set on The Old Sawmill within the village of Bolsterstone, Peak District. Outstanding views. Near National Park. Family-friendly. Penistone 6.4 miles; Sheffield 10 miles; Rotherham 12.7 miles. (Ref. 1066252)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Baby-friendly
  • 10% off - Wed 6th Jan to 29th Jan 2027


for 7 nights From £491

Last booked 8 hours ago
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  • Sleeps3
  • Bedrooms2
  • Pet FriendlyNo

    4.6

    Outstanding

  • Sykes rating

Win Hill View is a pleasant property situated close to a railway station in Bamford, Peak District with enclosed garden. Hathersage 1.9 miles; Castleton 4.6 miles; Sheffield 13.2 miles; Buxton 14.5 miles. (Ref. 1168054)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine


for 7 nights From £400

Last booked yesterday
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  • Sleeps8
  • Bedrooms4
  • Pet FriendlyNo

    4.9

    Outstanding

  • Sykes rating

Outstanding barn conversion on the outskirts of the small village of Midhopestones. Sleeps eight, four bedrooms. Exposed beams and stonework. Wonderful countryside views. Large garden. Holmfirth 10 miles. (Ref. 6188)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine


for 7 nights From £786

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    5.0

    Perfect

  • Sykes rating

The Reading Room, a stunning reverse-level house in Grindleford, Derbyshire, set within Peak District National Park, offers a fire pit and allows pets. Hathersage 2.6 miles; Castleton 8.3 miles; Sheffield 11.2 miles. (Ref. 1196410)

  • Pets go free
  • Wi-fi
  • Ground floor bedroom
  • Washing machine


for 7 nights From £652

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.6

    Outstanding

  • Sykes rating

A stunning cottage hidden in Oughtibridge, Sheffield. Open-plan. Hot tub. Off-road parking. Beautiful views. Sheffield 6.2 miles; Rotherham 10.2 miles; Castleton 16 miles. (Ref. 1106982)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Hot Tub
  • Washing machine


for 7 nights From £814

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyYes

    5.0

    Perfect

  • Sykes rating

Rock Mill Holiday Apartments is a stunning, third-floor apartment resting in Stoney Middleton, near Calver, Derbyshire. In Peak District National Park. Off-road parking. EV Charging. Calver 1 mile; Bakewell 5.7 miles; Sheffield 12.9 miles. (Ref. 1130694)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • 5% off - Fri 7th Aug to 31st Aug 2026


for 7 nights From £495