Find My Favourite Holiday Cottages in Oswestry

If enjoying one country on holiday isn’t enough, then a holiday house in Oswestry sitting on the English/Welsh border is the perfect base to explore either side of the border. Oswestry, a rural market town in Shropshire, is one of the oldest borderland settlements in the UK. Close proximity to Wales gives Oswestry an exciting mix of culture, with traditional English Inns and thatched holiday houses contrasting nicely with the many Welsh place names and Welsh-speaking locals in the town.

Exterior view of a stonebuilt, L-shaped barn conversion in the Shropshire Countryside.
Castell Courtyard, Oswestry
Oswestry
Shropshire
England
Sleeps
24
Bedrooms
9

Castell Courtyard is a large holiday cottage with a hot tub on a working sheep farm in the beautiful Shropshire Countryside. It sleeps up to 24 guests in 11 bedrooms near Oswestry and is perfect for walking holidays in the Tanet Valley and Berwyn Mountains.

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ATudor farmhouse with timbered beam and overhanging floor overlooks a mature garden.
Top Farm House in Shropshire
Oswestry
Shropshire
England
Sleeps
13
Bedrooms
7

Top Farm House exudes rural charm. The Grade II listed 17th-century farmhouse in Knockin is surrounded by the Shropshire countryside and boasts original beams, uneven floors and antique furnishings, as well as a wood-burning stove, Aga, baby grand piano, four-poster bed, playroom & lovely gardens.

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Front of a log cabin showing a covered deck.
Cedar Log Cabin at Brynhallt
Ellesmere
Shropshire
England
Sleeps
4
Bedrooms
2

This hand-built and wonderfully fitted log cabin in Shropshire oozes charm and romance. The entire cabin, from the bold exterior to the charming interior, was designed with Western Red Cedar and thoughtfully furnished to ensure that the country charm is carried throughout his eco cottage in Ellesmere.

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Oswestry, and in particular the surrounding area, is steeped in history. Whittington Castle is just a few miles outside of Oswestry. Much of the original fortification still stands, and the striking castle and picturesque grounds are open to visitors in the latter half of the week. The Old Oswestry Hill Fort is just outside the town and can be accessed via a footpath from the playing fields on the edge of town. The spectacular forts are said to be the birthplace of Guinevere, and on a clear day, you can see as far as Nesscliffe to the South and Wrexham to the North.

The market in Oswestry is regarded as one of the best in the UK. With over 70 traders, an indoor, outdoor, and farmer’s market spread throughout the week. It’s the ideal place to grab some superb local produce! There’s a large Sainsbury’s near the town centre for all your supplies during your stay and plenty of country inns and restaurants serving delicious food and drinks to discover. The town is famous for its many public houses, around 40 today, many of which offer real ale from local breweries.

A holiday cottage in Oswestry is an excellent base for exploring some fantastic places in England and Wales. Many of the Welsh Mountains, along with the Coed y Brenin and Gwydyr Forest Parks, are easily accessible from Oswestry, making for a great day out. The English town of Shrewsbury has a largely unaltered medieval street plan and 660 beautiful listed buildings in the town centre alone, making it an attractive and charming area to wander from one landmark to another by way of some enticing independent shops.