Holiday Cottages Oswestry

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Your Oswestry/Croeswallt, Shropshire search returned 136 cottages

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  • Sleeps4
  • Bedrooms2
  • PetsYes
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Little Barn is a gorgeous, stone period cottage situated in the rural village of Trefonen, Shropshire, enjoying a toasty woodburning stove and a Smart TV. Oswestry 2.9 miles; Llanhaeadr-ym-Mochnant 10.6 miles; Shrewsbury 20.2 miles. (Ref. 1172562)

  • Wi-fi
  • Off-road parking
  • Washing machine
  • Baby-friendly

7 nights from £345

Last booked yesterday
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  • Sleeps6
  • Bedrooms3
  • PetsYes

    5.0

    Perfect

  • Sykes rating

Pennall Cottage is a lovely property near Knockin, Shropshire, boasting countryside views to admire, a woodburning stove and a hot tub in the front garden. Oswestry 3.5 miles; Shrewsbury 15.5 miles. (Ref. 935032)

  • Wi-fi
  • Off-road parking
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £641

  • Sleeps5
  • Bedrooms2
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

This idyllic terrace property rests within the centre of Llangollen. Pet-friendly. WiFi. Pub and shop within 0.1 mile. Chester 23.6 miles. (Ref. 1014939)

  • Wi-fi
  • Dishwasher
  • Washing machine

7 nights from £412

Last booked yesterday
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  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

1 Clarkes Lane is a beautiful cottage nestled in the quaint village of St Martins in Shropshire. Woodburning stove. Hot tub. Pet-friendly. Games room. Oswestry 5.3 miles; Llangollen 9.8 miles; Shrewsbury 22.4 miles; Chester 23.5 miles. (Ref. 1159443)

  • Wi-fi
  • Off-road parking
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room

7 nights from £862

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  • Sleeps5
  • Bedrooms3
  • PetsNo

    5.0

    Perfect

  • Sykes rating

A superb, three bedroom barn conversion set in the Ceiriog Valley overlooking the Chirk Aqueduct and Viaduct close to Chirk. Welcoming character property with modernised fixtures and features. Chirk 1 mile. (Ref. 929056)

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

7 nights from £442

  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0

    Perfect

  • Sykes rating

A traditional and rustic property boasting contemporary charm, this detached dwelling is perfect for your family getaway to Shropshire. Ideal for exploring both England and Wales. Open-plan living. Countryside views. On a working farm. Trefonen 2.7 miles. (Ref. 986887)

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

7 nights from £407

  • Sleeps2
  • Bedrooms1
  • PetsYes

    5.0

    Perfect

  • Sykes rating

Well-appointed barn conversion nestled close to the Wales/England border, some 8 miles from the centre of Oswestry. WiFi. Pet-friendly. Off-road parking. Enclosed garden. Llanymynech 4.1 miles. (Ref. 1000425)

  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Ground floor bedroom
  • Dishwasher
  • Washing machine

7 nights from £416

  • Sleeps12
  • Bedrooms4
  • PetsYes

    4.8

    Outstanding

  • Sykes rating

The Willows is a detached holiday home nestled in the outskirts of Llangollen in Denbighshire with a great location and views plus a great games room. Ruthin 17.1 miles; Chester 24.3 miles. (Ref. 1160642)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room

7 nights from £1357

Last booked yesterday
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  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

A homely cottage situated close to the village of West Felton in Shropshire. Conservatory. Pet-friendly. Enclosed garden. En-suite. Oswestry 6.3 miles; Shrewsbury 14.6 miles; Wrexham 19.2 miles. (Ref. 977441)

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

7 nights from £371

  • Sleeps14
  • Bedrooms7
  • PetsYes

    5.0

    Perfect

  • Sykes rating

Tanat House is a wonderful, pet-friendly detached holiday home situated in the outskirts of of Nantmawr in Shropshire with an indulgent private hot tub. Oswestry 4.1 miles; Llanhaeadr-ym-Mochnant 9.2 miles; Shrewsbury 19.7 miles. (Ref. 1155356)

  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room

7 nights from £2310

  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Superb detached cottage in beautiful country location. Woodburning stove, WiFi. Llangollen 9 miles. (Ref. 916332)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • 15% off - Sat 12th Jul to 19th Jul 2025

  • 10% off - Sat 19th Jul to 26th Jul 2025

7 nights from £493

  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Threshers Barn is a stunning, pet-friendly house resting in Weston Rhyn, Shropshire, boasting open-plan living, underfloor heating, and woodburning stove. Oswestry 4.9 miles; Wrexham 10.6 miles; Whitchurch 20.5 miles; Chester 22.5 miles. (Ref. 1169526)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room

7 nights from £750

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.7

    Outstanding

  • Sykes rating

Bryn Golau is an attractive, detached stone cottage in Glyn Ceiriog in North Wales. Woodburning stove. Family-friendly. Dog-friendly. Great views. Llangollen 5.2 miles. Wrexham 16.3 miles. Chester 28.5 miles. (Ref. 1149555)

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

7 nights from £587

  • Sleeps5
  • Bedrooms3
  • PetsYes

    5.0

    Perfect

  • Sykes rating

A beautiful, detached, Welsh cottage, set in the Ceiriog Valley, two miles from Glyn Ceiriog. Peaceful countryside views. Character features and contemporary design. Woodburning stove. WiFi. Llangollen 7 miles. (Ref. 939502)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Sky TV

7 nights from £493

  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0

    Perfect

  • Sykes rating

This charming semi-detached cottage rests next to the Shropshire Union Canal in the area of Henlle, Shropshire. Woodburning stove. Garden with seating. Off-road parking. Oswestry 5 miles; Llangollen 8.7 miles; Shrewsbury 22.2 miles. (Ref. 1057460)

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

7 nights from £613

  • Sleeps10
  • Bedrooms5
  • PetsYes

    5.0

    Perfect

  • Sykes rating

Pentre Hall is a characterful, five-bedroom property in Bronygarth near Chirk, Shropshire. Clwydian Range and Dee Valley AONB. Original features. Hot tub. Oswestry 5.7 miles; Llangollen 8.8 miles; Chester 24.4 miles. (Ref. 1112629)

  • Wi-fi
  • Off-road parking
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £1595

  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Outstanding

  • Sykes rating

Beautiful barn conversion located between Ellesmere and Shrewsbury, near the market town of Wem. Conservatory with hot tub. WiFi. (Ref. 998662)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Hot Tub
  • Dishwasher
  • Washing machine

7 nights from £620

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0

    Perfect

  • Sykes rating

Border View Lodge is a detached barn conversion resting in Bulthy near Llandrinio, Shropshire. Countryside. Hot tub. Woodburning stove. Lovely view. Llandrinio 6.2 miles; Oswestry 13 miles; Shrewsbury 13.1 miles. (Ref. 1053933)

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

7 nights from £710

  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.9

    Outstanding

  • Sykes rating

Stunning barn conversion near the Powys village of Llanrhaeadr-ym-Mochnant. Countryside views. Open-plan. All en-suite bedrooms. Hot tub. (Ref. 912237)

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

7 nights from £680

  • Sleeps2
  • Bedrooms1
  • PetsYes

    5.0

    Perfect

  • Sykes rating

Willow Grange Annex is a lovely, dog-friendly annex resting in The Trench, Shropshire, boasting stunning countryside views and an open-plan living space. Oswestry 10.1 miles; Shrewsbury 18.6 miles; Chester 25.9 miles. (Ref. 1173020)

  • Wi-fi
  • Off-road parking

7 nights from £375

 

Just Show Me Oswestry Cottages

Straddling the Anglo-Welsh border, our Oswestry holiday cottages are firm favourites with lovers of history and countryside. Once an important frontier town, an ancient hill fort looms high above while Offa's Dyke National Trail marks the boundary. This unique setting allows you to pop in and out of England and Wales as many times as you like during your Oswestry cottage stay, giving you a real feel for the fusion of cultures.

On the Welsh side are historic treasures like the castles of Chirk, Powis and Whittington, said to be the former home of that famous pantomime character! Natural delights, meanwhile, include Lake Vyrnwy and Pistyll Rhaeadr waterfall, the highest in Wales.

Also close to your holiday home in Oswestry is the spectacular Pontcysyllte Aqueduct World Heritage Site, built by Thomas Telford - if you've a head for heights, experience mind-boggling scenery and travel across by horse-drawn barge.

Family days out include woodland walks and picnics in Nesscliffe Country Park, mini Land Rover rides and more at the award-winning Park Hall Farm and many other fantastic days out in and around Oswestry in Shropshire.

Exploring Oswestry

Back in town, join a themed walking tour and discover Oswestry's nooks and crannies. Much of the centre is a designated Conservation Area, with a wonderful mix of architectural styles. Dip in and out of the attractive shops, the tempting eateries and cosy pubs. And don't miss a trip to the market (three days a week) or monthly farmers' market.

Did you know Oswestry was voted one of the 'coolest places to live in England'? Find out for yourself and book that Oswestry cottage holiday soon!