Holiday Cottages Oswestry

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British Travel Award Winners!

We are delighted to announce that we have been awarded 'Best UK Holiday Cottage/Self Catering Booking Company' at the British Travel Awards.

Holiday Cottages Oswestry

REFINE SEARCH

Your Oswestry/Croeswallt, Shropshire search returned 135 cottages

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Map View
Stone buildings with slate roofs and solar panels surrounded by garden and trees at Little Cow House in Pontfaen near Chirk
35
Pontfaen near Chirk, Shropshire, LL14
  • Sleeps5
  • Bedrooms3
  • PetsNo

    5.0

    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

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A stone and wood house with a fenced lawn and a wooden gate at The Old Cart House in Nantmawr near Trefonen
33
Nantmawr near Trefonen, Shropshire, SY10
  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0

    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 £416

Last booked yesterday
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A brick house with a slate roof and wooden fence surrounded by plants and trees at The Tractor Shed in Kinnerley near Oswestry
25
Kinnerley near Oswestry, Shropshire, SY10
  • Sleeps2
  • Bedrooms1
  • PetsYes

    5.0

    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

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A stone and timber house with a gravel driveway and garden at Pentre Hall in Bronygarth near Chirk
70
Bronygarth near Chirk, Shropshire, SY10
  • Sleeps10
  • Bedrooms5
  • PetsYes

    5.0

    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

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An outdoor patio area with seating and a fire pit by a stone house with ivy and a pond with water lilies in the foreground at Tanat House Nantmawr near Trefonen
86
Nantmawr near Trefonen, Shropshire, SY10
  • Sleeps14
  • Bedrooms7
  • PetsYes

    5.0

    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

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A stone building exterior with doors windows and lights on a paved walkway at Threshers Barn in Weston Rhyn
New property
46
Weston Rhyn, Shropshire, SY10
  • Sleeps8
  • Bedrooms4
  • PetsYes

    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

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A white stone house with a slate roof surrounded by bushes and a tree along a driveway at Penymaes in Bronygarth near Chirk
Offer
31
Bronygarth near Chirk, Shropshire, SY10
  • Sleeps5
  • Bedrooms3
  • PetsNo

    4.9

    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

  • 5% off - Sat 14th Jun to 21st Jun 2025

  • 5% off - Sat 12th Jul to 26th Jul 2025

7 nights from £493

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A wooden house with glass sliding doors a small deck with potted plants and a green lawn at Vitula Cottage Burlton near Wem
32
Burlton near Wem, Shropshire, SY4
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    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

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An exterior view of a white house with large wooden windows and a stone wall in front at Pen Y Bont in Glyn Ceiriog
22
Glyn Ceiriog, Wrexham, LL20
  • Sleeps5
  • Bedrooms3
  • PetsYes

    5.0

    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

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A two story house with white walls a gray roof and a garden with trees and bushes at Belmont Bridge in Henlle
35
Henlle, Shropshire, SY10
  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0

    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

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A white two-story house with a stone patio and garden chairs near a gravel driveway at Bryn Celyn in Trefonen
34
Trefonen, Shropshire, SY10
  • Sleeps10
  • Bedrooms5
  • PetsYes

    4.8

    Sykes Rating

This detached holiday cottage rests in the peaceful village of Trefonen in Shropshire. Pet-friendly. Woodburning stove and open fire. Enclosed garden. Oswestry 2.9 miles; Shrewsbury 20.5 miles. (Ref. 1053089)

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

7 nights from £857

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The exterior of a house with stone and white walls a wooden door and a black chair on a gravel path at Bryn Golau in Glyn Ceiriog
39
Glyn Ceiriog, Wrexham, LL20
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.7

    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

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A brick house with a gravel driveway and garden at 1 Clarkes Lane in St Martins
47
St Martins, Shropshire, SY11
  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.9

    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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A stone cottage with a wooden door and picket fence under a blue sky at The Laurels Barn in West Felton near Oswestry
27
West Felton near Oswestry, Shropshire, SY11
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    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

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A gravel courtyard with a white door and potted plants next to a brick building at Willow Grange Annex in The Trench near Ellesmere
New property
27
The Trench near Ellesmere, Shropshire, SY12
  • Sleeps2
  • Bedrooms1
  • PetsYes

    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

Last booked yesterday
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Exterior view of a brick house with paved driveway plants and flower pots at Plum Hill in Morda near Oswestry
44
Morda, near Oswestry, Shropshire, SY10
  • Sleeps6
  • Bedrooms3
  • PetsNo

    5.0

    Sykes Rating

Plum Hill is a traditional first-floor apartment in the village of Morda, near Oswestry in Shropshire. Gas stove. Off-road parking. Rural views. Llangollen 15.2 miles; Welshpool 14.5 miles; Shrewsbury 19.2 miles. (Ref. 1151783)

  • Wi-fi
  • Off-road parking
  • Dishwasher

7 nights from £431

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A street with a row of white and black timber framed houses and a blue car parked at the end of the road at 21 Church Street in Llangollen
33
Llangollen, Denbighshire, LL20
  • Sleeps5
  • Bedrooms2
  • PetsYes

    4.7

    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 2 days ago
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A brick house with driveway potted plants and trees at Plum Hill Studio in Oswestry
19
Oswestry, Shropshire, SY10
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Sykes Rating

A cosy, ground floor studio apartment located just outside of Oswestry in Shropshire. Open plan. Delightful lawn. Oswestry 1 mile. (Ref. 963200)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher

7 nights from £300

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A two-story house with a gravel driveway and a large outdoor chess set on a lawn at Cwmalis Hall in Llangollen
53
Llangollen, Denbighshire, LL20
  • Sleeps16
  • Bedrooms8
  • PetsYes

    4.7

    Sykes Rating

A Grade II listed, detached property close to Llangollen in North Wales. Countryside views. Hot tub. Games room. Llangollen 2.7 miles; Ruthin 17.8 miles; Chester 23.5 miles. (Ref. 1001247)

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

7 nights from £2212

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The front view of a red brick building with arched windows and a blue door at Wesleyan House in Gobowen
33
Gobowen, Shropshire, SY11
  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.9

    Sykes Rating

This stunning chapel conversion rests in the charming village of Gobowen in Shropshire. Off-road parking. Smart TVs. Characterful. Ground-floor bedroom. Oswestry 3.2 miles; Ellesmere 7.6 miles; Shrewsbury 20.3 miles; Chester 23.9 miles. (Ref. 1087579)

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

7 nights from £772

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Map View

 

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!