Holiday Cottages near Sheffield

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

  • 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 $760

Last booked yesterday
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  • 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 $1680

  • 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 $1195

  • 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 $726

Last booked 2 days ago
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  • 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 $704

  • 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 $1395

  • 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 $1633

  • 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 $655

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 $1038

  • 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 $524

  • 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 $1075

Last booked 1 hour ago
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  • 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 $692

Last booked 6 hours ago
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  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.6

    Outstanding

  • Sykes rating

Wigley Farm House Cottage is a fabulous pet-friendly bungalow near Chesterfield, Derbyshire, boasting a woodburning stove, a hot tub and countryside views. Chatsworth 6.7 miles; Bakewell 8.3 miles; Matlock 9.9 miles. (Ref. 1182208)

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


for 7 nights From $929

  • Sleeps5
  • Bedrooms3
  • Pet FriendlyYes

    4.8

    Outstanding

  • Sykes rating

A lovely, semi-detached stone cottage set on the outskirts of the village of Wortley. Rural surroundings. Pet-friendly. Sheffield 10.5 miles. (Ref. 1010259)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Dishwasher


for 7 nights From $514

Last booked yesterday
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  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.6

    Outstanding

  • Sykes rating

A fresh barn conversion on the outskirts of Hathersage in the Peak District National Park. Arrow loop windows. Views of Hope Valley. En-suite shower room. Castleton 5 miles. (Ref. 952359)

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


for 7 nights From $1342

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    4.9

    Outstanding

  • Sykes rating

A gorgeous converted workshop set in the village of Bolsterstone near Stocksbridge, Peak District. Stylish interiors. Pet-friendly. Countyside views. Penistone 6.4 miles; Sheffield 10 miles; Rotherham 12.7 miles. (Ref. 1066253)

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


for 7 nights From $655

Last booked yesterday
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  • 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 $856

Last booked yesterday
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  • Sleeps2
  • Bedrooms1
  • Pet FriendlyYes

    4.9

    Outstanding

  • Sykes rating

A charming Stocksbridge cottage on the edge of the Peak District National Park. Romantic retreat, king-size bed with en-suite. Holmfirth 12 miles. (Ref. 3839)

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


for 7 nights From $429

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.8

    Outstanding

  • Sykes rating

Smithy Cottage, a well-appointed, two-bedroom cottage rests in Barlow near Chesterfield, Derbyshire. Near National Park. Contemporary. Close to amenities. Private driveway. Chatsworth 9.1 miles; Bakewell 10.6 miles; Matlock 12.8 miles. (Ref. 1132596)

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


for 7 nights From $551

  • Sleeps8
  • Bedrooms4
  • Pet FriendlyYes

    4.6

    Outstanding

  • Sykes rating

A wonderfully spacious detached property accompanied by a delightful shepherd's hut next door, nestled on the edge of Bolsterstone village near the Peak District. Hot tub; sauna. Pizza oven; BBQ. Modern design. Shop and pub 10 mins walk. (Ref. 982384)

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


for 7 nights From $1296