Holiday Cottages Oswestry

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Holiday Cottages Oswestry

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Your Oswestry/Croeswallt, Shropshire search returned 136 cottages

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Map View
Exterior view of a stone cottage with a blue door and multiple windows at Dovetail Cottage in Llangollen
21
Llangollen, North Wales & Snowdonia, LL20
  • Sleeps3
  • Bedrooms2
  • PetsNo

    4.8

A semi-detached holiday cottage in Llangollen, North Wales. Feature stone walls and exposed beams. Enclosed patio. Town centre 2 mins walk. (Ref. 912854)

  • Wi-fi
  • Off-road parking
  • Dishwasher

7 nights from £275

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A brick house with two dormer windows and glass doors on a gravel driveway at Gwdihw in Gobowen
14
Gobowen, Shropshire, SY10
  • Sleeps3
  • Bedrooms2
  • PetsNo

    4.9

    Sykes Rating

A delightful rural cottage surrounded by countryside. Two bedrooms, open plan living area. Countryside walks and cycle rides from the door. Oswestry 4 miles (Ref. 951869)

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

7 nights from £336

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 £288

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A white two-story house with multiple windows and chimney surrounded by a lawn and plants at The Cottage in Llangollen
19
Llangollen, Wrexham, LL20
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8

    Sykes Rating

A welcoming Cottage situated in Garth near Llangollen, in Denbighshire. Fine valley views. Exposed beams. WiFi. (Ref. 967433)

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

7 nights from £331

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A small stone cottage with a tiled roof and wooden door next to a patio with chairs and a table at Byre Cottage Nesscliffe near Shrewsbury
13
Nesscliffe near Shrewsbury, Shropshire, SY4
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Sykes Rating

Detached stone-built barn conversion, set one mile from Nesscliffe village. Character beams and trusses. Well-equipped, open plan accommodation. Shrewsbury 8 miles. (Ref. 906694)

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

7 nights from £336

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A small green cabin with open doors on a stone patio surrounded by chairs and a wooden fence near trees on a grassy hillside at The Moorhen Retreat in Nantmawr near Trefonen
20
Nantmawr near Trefonen, Shropshire, SY10
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Sykes Rating

A lovely studio-style shepherds hut resting in Nantmawr, Shropshire. Open-plan. Wood-fired hot tub. Romantic. Smart TV. Off-road parking. Country views. Oswestry 5.8 miles; Llanhaeadr-ym-Mochnant 7.8 miles; Shrewsbury 20.6 miles. (Ref. 1070634)

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

7 nights from £445

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Exterior of a stone and brick house with wooden windows and door at The Cart House in Alberbury
21
Alberbury, Shropshire, SY5
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Sykes Rating

The Cart House is a delightful single-storey abode full of character with a steamy hot tub and woodburning stove, in the village of Alberbury, Shropshire. Shrewsbury 10.2 miles; Powis Castle 16.9 miles. (Ref. 1164516)

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

7 nights from £471

Last booked yesterday
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A kitchen with wooden dining table and four upholstered chairs wooden ceiling beams and light gray cabinets at Ascot in Knolton near Ellesmere
26
Knolton near Ellesmere, Wrexham, LL13
  • Sleeps2
  • Bedrooms1
  • PetsNo

    Sykes Rating

Ascot, a charming cottage located on an adults-only holiday park in the hamlet of Knolton near Ellesmere, Wrexham. Romantic. Smart TV. Open-plan. Oswestry 11.1 miles; Shrewsbury 20.1 miles. (Ref. 1161488)

  • Wi-fi
  • Dishwasher

7 nights from £392

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A dome tent on a wooden platform with outdoor chairs and clawfoot bathtubs at Meadow View - Bryn-Mawr Retreat in Brynmawr near Llanymynech
13
Brynmawr near Llanymynech, Powys, SY22
  • Sleeps2
  • Bedrooms1
  • PetsNo

    Sykes Rating

Meadow View - Bryn-Mawr Retreat is a unique, single-storey glamping pod tucked away in the rolling countryside of Brynmawr near Llanymynech, Powys. Llandrinio 3.2 miles. Owestry 7.9 miles. (Ref. 1170384)

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

7 nights from £345

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An outdoor area with a wooden hot tub a gravel ground stepping stones a pod with chairs and a wooden fence at Heron Pod in Nantmawr near Trefonen
22
Nantmawr near Trefonen, Shropshire, SY10
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Sykes Rating

Heron Pod is a charming, contemporary pod resting in the countryside of Nantmawr near Trefonen, Shropshire, with a hot tub and rural location. Trefonen 2.7 miles; Oswestry 5.7 miles. (Ref. 1144522)

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

7 nights from £487

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The exterior of a light green wooden shepherds hut with open doors on a gravel surface with a hill in the background at Tan Y Castell Shepherds Hut in Llangollen
18
Llangollen, Denbighshire, LL20
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9

    Sykes Rating

A wonderful, single-storey shepherds hut residing in Llangollen, Denbighshire. Off-road parking. Romantic. Rural. Ground-floor living. Ruthin 17.7 miles; Chester 21.5 miles. (Ref. 1135593)

  • Off-road parking
  • Ground floor bedroom

7 nights from £328

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A garden patio with two reclining chairs yellow flowers a small table with two chairs a bench and a wooden gate at Cam O'r Fechan Annexe in Llangollen
29
Llangollen, Denbighshire, LL20
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0

    Sykes Rating

A single-storey annexe lying on the luscious outskirts of Llangollgen in North Wales. Single-storey. Open-plan living. Countryside views. Romantic. Private terrace with furniture. Ruthin 17.2 miles; Mold 23.1 miles; Chester 24.9 miles. (Ref. 1110492)

  • Wi-fi
  • Off-road parking

7 nights from £360

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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

    5.0

    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

Last booked 9 hours ago
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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 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

    5.0

    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 £366

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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 brick house with windows a large paved driveway and a hedge on the left at Plum Hill Apartment in Morda near Oswestry
13
Morda, near Oswestry, Shropshire, SY10
  • Sleeps2
  • Bedrooms1
  • PetsYes

    5.0

    Sykes Rating

A charming ground floor apartment looking onto idyllic countryside. Open plan living accommodation. En-suite shower room. Pet-friendly. Perfect touring base. Oswestry 1.5 miles. (Ref. 949423)

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

7 nights from £339

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Stabl, Plas Moelfre Hall Barns - 1020502 - photo 1
Offer
25
Moelfre near Llanrhaeadr-Ym-Mochnant, Powys, SY10
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9

    Sykes Rating

This is a detached cottage situated in Moelfre near to Llanrhaeadr-Ym-Mochnant in Powys. En-suite bathroom. Reverse level accommodation. Hot tub. Oswestry 7.8 miles; Lake Vyrnwy 17.4 miles; Bala 23.9 miles. (Ref. 1020502)

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

  • 3% off - Fri 4th Jul to 1st Aug 2025

7 nights from £526

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Front door with green paint and heart decoration with two potted plants and a window on a white brick cottage at Top Farm Cottage in Knockin
16
Knockin, Shropshire, SY10
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.7

    Sykes Rating

A delightful semi-detached cottage resting in Knockin, Shropshire. Ground-floor living. Romantic retreat. Rural setting. Oswestry 5.7 miles; Shrewsbury 13.5 miles. (Ref. 1059788)

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

7 nights from £361

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A kitchen and dining area with wooden beams on the ceiling and a wooden table with four chairs at Bangor in Knolton near Ellesmere
26
Knolton near Ellesmere, Wrexham, LL13
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.8

    Sykes Rating

Bangor, a romantic cottage located on an adults-only holiday park in the hamlet of Knolton near Ellesmere, Wrexham. Smart TV. Open-plan. Pet-friendly. Oswestry 11.1 miles; Shrewsbury 20.1 miles. (Ref. 1161491)

  • Wi-fi
  • Off-road parking
  • Dishwasher

7 nights from £375

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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!