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 133 cottages

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Map View
A white cottage with a gravel driveway wooden seating area and hedges at Pennal Cottage in Maesbury Marsh near Knockin
New property
41
Maesbury Marsh near Knockin, Shropshire, SY10
  • Sleeps6
  • Bedrooms3
  • PetsYes

    5.0

    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

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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

Last booked yesterday
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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 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 £1474

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The exterior of a single story house with a tiled roof and a conservatory next to a paved patio at The Willows in Llangollen
71
Llangollen, Denbighshire, LL20
  • Sleeps12
  • Bedrooms4
  • PetsYes

    4.8

    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

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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 £407

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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

Last booked 3 hours ago
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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
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

7 nights from £493

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

    4.8

    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 £774

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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

    4.8

    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 £818

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White exterior of a house with grey window frames and door with plants outside at Little Beeches in Hengoed
22
Hengoed, Shropshire, SY10
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.9

    Sykes Rating

Tremendous, semi-detached cottage well-placed in the village of Hengoed, Shropshire. Exposed stonework. WiFi. Llangollen 10 miles. (Ref. 958275)

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

7 nights from £379

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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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Little Barn - 1172562 - photo 1
New property
33
Trefonen, Shropshire, SY10
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7

    Sykes Rating

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 £374

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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 £856

Last booked yesterday
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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 £2321

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A house with a garden and patio furniture at 2 Mountain View in Chirk
48
Chirk, Wrexham, LL14
  • Sleeps6
  • Bedrooms3
  • PetsYes

    Sykes Rating

2 Mountain View, a welcoming bungalow resting in the outskirts of the town of Chirk in Wrexham. Near to a shop. Near to a pub. Pet-friendly. Open fire. Wrexham 8.9 miles; Clwydian Range & Dee Valley National Landscape 16.6 miles. (Ref. 1157883)

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

7 nights from £490

Last booked yesterday
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A driveway in front of two brick and timber framed buildings with outdoor chairs and potted plants at The Wynnstead Annexe Queen's Head near Oswestry
20
Queen's Head near Oswestry, Shropshire, SY11
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Sykes Rating

This first floor apartment is set above a garage in the owner's grounds and is an ideal romantic retreat. Private patio, short walk to pub and canal. Oswestry 4 miles. (Ref. 954032)

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

7 nights from £333

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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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Front entrance of a timber framed house with a wooden door and a black mailbox at 18 Church Street in Llangollen
41
Llangollen, Denbighshire, LL20
  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0

    Sykes Rating

18 Church Street is a restored, Grade II listed home in the heart of Llangollen, Denbighshire. Original features. Near amenities and river. Pet-friendly. Ruthin 15.7 miles; Chester 23.4 miles. (Ref. 1095762)

  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly

7 nights from £581

Last booked yesterday
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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 £274

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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!