farmhouse and out-buildings surrounded by mature gardens. Smallshaw Farm Cottages in Penistone.

Find My Favourite Holiday Cottages in South Yorkshire

The county of South Yorkshire covers 600 square miles and includes the boroughs of Barnsley, Doncaster, Rotherham and Sheffield. It lies on the eastern edge of the Pennines and borders the rest of Yorkshire, Lincolnshire, Derbyshire and Nottinghamshire. Holiday cottages in South Yorkshire are popular among visitors who want to discover the county’s dramatic landscapes of craggy hills and deep valleys. The countryside is crossed by the rivers Dearne, Rother and Don, and is dotted with the remains of mining buildings, steel plants and spoil heaps. On the doorstep of your South Yorkshire holiday cottage, The Peak District National Park is an enchanting expanse of vales, high moorland and jagged gritstone edges, scattered with peaceful villages and opulent country homes. The park is crisscrossed by scenic trails and has exceptional sites for rock climbing, caving and other outdoor pursuits.

Sleeps
6
Bedrooms
3

The Farmhouse is a dog-friendly 3-bedroom Yorkshire Farmhouse in Penistone, offering glorious rural views right across to the Peak District. Sleeps 6. Perfect for walking and cycling holidays in The Pennines.

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Gable end of a 2-storey pennine holiday cottage overlooking a country lane
Sleeps
2
Bedrooms
1

Underbank Hall Cottage is a romantic cottage for couples in a secluded rural location with breathtaking views of the valleys and hills between The Peak District and The Pennines in Stocksbridge, but still within easy reach of the fleshpots of Sheffield. Pets welcome.

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Sleeps
15
Bedrooms
7

It may look Victorian, but Hartcliffe View is a large, sumptuously furnished, modern house in a rural location, standing in moorland on the edge of the Peak District near Penistone in South Yorkshire. This dog-friendly holiday cottage sleeps 15. It has a games room and football pitch in the garden.

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Sleeps
19
Bedrooms
8

Luxuriously large barn conversion Yorkshire Pennine cottages, we have four properties here at Smallshaw Farm near Penistone, sleeping from 2 - 7 (19 people in all). Surrounded by 700 acres of open farmland with a large garden area. Dogs welcome.

  • Accessible Cottages
  • Active Holidays
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  • Dog-Friendly Holiday Cottages
  • Farm Cottages
  • Independent Cottages
  • Large Holiday Cottages
  • Luxury Holiday Cottages
  • Remote Cottages
  • Romantic Cottages

South Yorkshire has a wealth of historical sites, including Monk Bretton Priory, Conisborough Castle and Roche Abbey. Yorkshire Wildlife Park, Elescar Steam Railway and Woodlands Model Village are recommended for family days out. Well worth a visit on self-catering holidays in South Yorkshire, Sheffield is a lively city with a fascinating history. It played an important role in the Industrial Revolution with its booming steel industry and the development of various inventions in the 19th century. The historic city centre is best explored on foot, with a variety of independent shops, a flourishing food scene, and an abundance of interesting landmarks and architecture to discover.

Another popular place to visit in South Yorkshire is Doncaster. In this charming market town, Norman castles, Regency architecture, and horse racing combine to create an atmosphere like nowhere else in the region. 18th-century Cusworth Hall, Potteric Carr Nature Reserve and South Yorkshire Aircraft Museum are all worth a visit.